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Vacation Rentals in Chicago, IL

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From
$149
Per Night
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1 / 15
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$159
Per Night
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1 / 11
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Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
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From
$195
Per Night
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1 / 15
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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$85
Per Night
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1 / 14
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a nice place on a quiet street, close to transportation and many restaurants. Very close to I 94. View all property information
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5 of 5 stars Reviewed January 12, 2015
The rental was EXCEPTIONAL! The Hannn was so nice and the unit couldn't have been better! My family absolutely loved it! Thanks again!
5 of 5 stars Reviewed December 3, 2014
Booking this flat was so, so much better than a hotel. It was less expensive, for a start, especially for a group of four. It was great to have multiple rooms so some could...
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From
$65
Per Night
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1 / 14
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Northwest Side
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (9) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The studio is situated in the couch house of the property. It is 300 square feet plus the bathroom. Beautiful decorated and very quiet place with the windows facing the beautiful garden. There is a washer and dryer on side and we can offer also breakfast. View all property information
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5 of 5 stars Reviewed September 20, 2014
The place is immaculate. Super clean and fully equipped. The location is great. You have the subway blue line (to downtown) in a short walk from the house to the station. The...
5 of 5 stars Reviewed September 1, 2014
I enjoyed my stay here and the hosts are warm, friendly and welcoming people. Hanne is just the sweetest person and I feel as if I have known her for many years. She always made...
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From
$250
Per Night
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1 / 10
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
**LOCATION **LOCATION **LOCATION! ***CAN'T BEAT IT! ***Views Views Views! Breathtaking Lake and City Views!!*** Looks Like Hawaii Up There!*** Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep of... View all property information
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5 of 5 stars Reviewed September 2, 2014
We're home from our trip and back to reality! We loved your City and will definitely be back, next time could you arrange a bit better weather please!! But, as Brits we're used to...
5 of 5 stars Reviewed July 22, 2014
We booked through Steps From Everything and they were very easy to work with. The price was very reasonable and the location was great. We could walk two blocks to the Metro...
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From
$75
Per Night
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1 / 16
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (32) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
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4 of 5 stars Reviewed December 10, 2014
Cheryl's apartment worked perfectly as a home base for my husband and me during a long weekend's visit to Chicago. We spent much of our time in and around the Loop, but found the...
5 of 5 stars Reviewed November 14, 2014
My husband and I rented the apartment for 5 days in early November. I was attending a Conference downtown and did not want to pay the high price hotel. This place was perfect...
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From
$99
Per Night
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1 / 7
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
If you are looking for a private, cozy, and comfortable place then this is just right for you. Here you can relax and lay back in a newly renovated unit with a private entrance for your convenience. Let the travel stress behind you and enjoy your stay in that great City we call HOME, Chicago We... View all property information
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From
$315
Per Night
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1 / 32
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Take me to the Penthouse! Stay in our Penthouse Condo on the 50th Floor! A true Penthouse, stunning views of the lake and city. Walk to everything downtown. Upgraded everything. Granite kitchen counter tops, stainless steal appliances, marble in the bathrooms, king size beds, floor to ceiling... View all property information
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5 of 5 stars Reviewed June 30, 2014
Can't sat enough good things about this place. Excellent host, great amenities, perfect location. Top shelf stay.
5 of 5 stars Reviewed August 15, 2011
Was a bit nervous booking the condo vs. a traditional hotel for a group of co-workers. Fantastic accommodations, great view, clean, convenient location. We already re-booked with...
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$75
Per Night
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1 / 18
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The Loop
Studio, 1 Bathroom, Sleeps 2
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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4 of 5 stars Reviewed August 20, 2014
Tr`es bien situé, propre et bien équipé. Personnel de l'immeuble bien chaleureux. Pitsfield's café `a ne pas manqué au rez-de-chaussée. Calme , bien insonorisé...`a l'exeption de...
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From
$120
Per Night
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1 / 49
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Southwest Side
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Reviews (30) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
We have two really incredible vacation rental apartments. We are offering great special off season rates for our Winter Months through March. These specials range from $110 per night to $195 per night and as low as $875 per week.. The best rates are for longer rentals and some dates will have... View all property information
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5 of 5 stars Reviewed November 13, 2014
Our family of four had an excellent time at this apartment. Bob was very easy to deal with and extremely helpful. Key code access to the apartment was very convenient. A garage...
4 of 5 stars Reviewed September 27, 2014
We were very pleased with our stay at this facility. It isn't in the typical touristy area which we liked as it made our urban experience feel more authentic and any neighbors we...
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From
$120
Per Night
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1 / 48
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Southwest Side
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (13) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
We have two really incredible vacation rental apartments. We are offering great special off season rates for our Winter Months through March. These specials range from $110 per night to $195 per night and as low as $875 per week.. The best rates are for longer rentals and some dates will have... View all property information
Make Inquiry
5 of 5 stars Reviewed April 7, 2014
Our family of four (two teens) spent 5 days here during spring break and had an excellent experience. We went downtown every day by catching the red line train at the 35th/Sox...
5 of 5 stars Reviewed May 2, 2012
We couldn’t be more pleased with our stay, everyone had a fantastic time. Our visit took place April 12-15 and there were six of us; my parents (early 50’s), younger brother and...
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From
$125
Per Night
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1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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4 of 5 stars Reviewed August 18, 2014
Very strategic location near to major attractions. Very spacious and quiet. The best coffee is just down the building! The only thing was the wifi was extremely slow, me and my...
3 of 5 stars Reviewed July 1, 2014
security was not aware of our check in and had to call and verify. kitchen is not adequately stocked for those who may use knives, forks and wine glasses. it was, however...
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From
$115
Per Night
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1 / 23
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Northwest Side, Wicker Park / Bucktown
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Chicago Bathhouse Corporate Residences are located on the 2nd floor of a 2 story building in Wicker Park Chicago. This vacation rentals are 2 bedrooms, 1 bathroom, 10 minutes from Chicago downtown. Close to restaurants, cafes. 5 min walk to Blue Line which takes you Downtown in 10 min... View all property information
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2 of 5 stars Reviewed October 14, 2014
I felt like I was being punked! When I booked this place it advertised access to the spa at the bath house. When we arrived the curt "receptionist" said access was only for one...
3 of 5 stars Reviewed June 15, 2014
This apartment in Wicker Park is enormous and very nice! It's in a pretty sweet location above a bathhouse and next to a great breakfast place called Milk & Honey. The el is about...
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From
$315
Per Night
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1 / 12
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (9) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Walk to Everything Downtown! Enjoy Stunning Views of the City Skyline and Grant Park! ONE OF FEW 3BD/2.5BA UNITS RIGHT IN THE MIDDLE OF DOWNTOWN CHICAGO. Very affordable! ***WALK TO EVERYTHING ***YES, THESE ARE THE VIEWS! ***BREATHTAKING VIEWS OF THE CITY SKYLINE AND GRANT PARK ***3... View all property information
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4 of 5 stars Reviewed October 30, 2014
This is a superb place to stay. Warm, comfortable with stunning views of downtown and Grant Park. We booked with stepstoeverything and their communications were top class...
5 of 5 stars Reviewed July 18, 2014
Pretty close to downtown parking is across the street Reservation and service are with phone communication, quick and helpful. Keyless entry Recent renovated with quality...
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From
$199
Per Night
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1 / 34
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Lincoln Square
5 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Huge 5 Bedroom-4.5 Bathroom home, 4 fire places, completely remodeled, fully furnished. Equipped kitchen with large breakfast island, separate dining room seating 8-10. Family room off the kitchen with fire place, huge deck and private back yard. Huge master bedroom with decorative fire place,... View all property information
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From
$1,000
Per Week
View Details
1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 3
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Perfect for short term stays in a great neighborhood. Available For weekly or monthly rentals Furnished for comfort and design, price includes all utilities and everything you need This completely furnished apartment is 1/2 block from the chicago avenue bus line, which runs straight to the blue... View all property information
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From
$80
Per Night
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1 / 17
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
1100 sq feet of your own space! Lots of room to stretch out here, two bedrooms, an office, living room, den, full kitchen, one bathroom, laundry in unit, back deck, backyard with apple tree (apples!!!), Keurig coffee maker, and parking right out front! Queen sized air mattress if needed. Free... View all property information
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From
$550
Per Night
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1 / 13
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Northwest Side
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Available ONLY 12/23/14- 12/29/14 We normally take 2 long vacations and are willing to rent our place. This house is fully furnished with a fully operational kitchen and full use of cooking utensils. Seating for up to 10 at dining room table. This house is best for someone looking to get their... View all property information
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From
$105
Per Night
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1 / 7
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (7) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Excellent Location: 1 block to the Navy Pier and lakefront 2 blocks to the shopping area on Michigan Ave Just on the other side of the river from Grant Park and Millennium Park (15 min walk) Large Unit: Largest 1bd/1ba floor plan downtown Wrap around windows, corner unit Full size kitchen,... View all property information
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4 of 5 stars Reviewed July 16, 2013
Our first visit to Chicago and we wanted to stay someplace with a great view--McClurg Court was wonderful for us. The apartment reminded us of a newly employed graduate who can...
4 of 5 stars Reviewed October 18, 2012
We stayed here for a week in October. The booking process and everything went well and we were given information relevant to our stay. The unit is in a fantastic location in...
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From
$65
Per Night
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1 / 12
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Northwest Side
Studio, 1 Bathroom, Sleeps 2
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This studio is situated in the garden of the property. Very quiet and peaceful setting. It has a Murphy bed and a jacuzzi. View all property information
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From
$199
Per Night
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1 / 16
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Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Village is a very family friendly neighborhood. This warm and welcoming first floor unit features a high end kitchen equipped with stainless appliances & granite countertops, 1 King... View all property information
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From
$120
Per Night
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1 / 23
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Live like a native in this artist-owned, artist-occupied vintage building located between the leading edge of the trendy Logan Square restaurant nexus and the old Polish neighborhood. Furnished in rustic Modern finds, it's on the Blue Line with easy access to the Loop and O'Hare. The unit has two... View all property information
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From
$110
Per Night
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1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Enjoy a great urban experience staying in the Ukrainian Village of Chicago! -- 2 bedroom flat perfect for short term stays. Convenient to shops, grocery, restaurants, library, bars, gym, swimming pool! THE SPACE: This main floor apartment includes the following amenities: Two comfortable bedrooms... View all property information
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From
$250
Per Night
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1 / 10
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Chicago Vacation Rental License # 2246788 This gorgeous 3 bedroom 2 bathroom unit is located on Damen Avenue, just steps away from the city's most trendy boutique shops and restaurants. The apartment will sleep 7 comfortably in beds, with one queen, two twins, one day-bed with a trundle, and a very... View all property information
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From
$395
Per Night
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1 / 8
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DePaul
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
HISTORY: Aster House has been renting since 1891, and under the present owners since 1982. We've had guests return as long as 18 years, so you may be assured of a safe secure visit. NEIGHBORHOOD: Aster House is on a quiet residential street in Lincoln Park, Chicago's most upscale downtown... View all property information
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From
$139
Per Night
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1 / 14
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden or Yard
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Welcome! Welcome! Our single family brick house is located in a rare semi-private block about 5 miles West of Downtown. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen. If you enjoy a quiet home with newer beds, clean sheets and towels, spaces, privacy, kitchen, laundry,... View all property information
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5 of 5 stars Reviewed July 18, 2014
Nice location. Everyone got their own beds. Easy to downtown. Kitchen and free laundry. Free Tide detergent too (not expected). Will stay again.
3 of 5 stars Reviewed May 7, 2014
The location of this property was great. It was about 12-15 minutes from downtown, which is where we wanted to be. There was plenty of on-street parking right in front of the...
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From
$149
Per Night
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1 / 10
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Housekeeping...
  • Internet Access
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This is a 3 Bed Room apartment of a two flat brick building in Andersonville area of Chicago. This apt has: 3 bedrooms, sleeps 8 Air Conditioners Free cell phone for international guests (plus deposit) Eat-in Kitchen Living Room Full size fridge Free parking Free laundry Complete kitchen Living... View all property information
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4 of 5 stars Reviewed July 10, 2014
I really enjoyed staying here. A great property. The sink did break while we were there but Jackie was right on getting it fixed for us! Great place, big enough for our group!
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From
$99
Per Night
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1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Plenty of free street parking is available on our block. This apt is very big and had a has a lot of natural sunlight. Located on the first floor of our building. We live upstairs in a completely separate apt so we are very close if you have any questions or concerns, but your privacy is assured.... View all property information
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4 of 5 stars Reviewed September 3, 2014
This was my first experience using Trip Advisor and renting a private home to stay in. The weekend was great. The apartment was located in a safe neighborhood to walk around in...
5 of 5 stars Reviewed November 11, 2013
From start to finish this rental was perfect. I was hesitant to rent from a private party, however great communication early on helped put me at ease. As a solo traveling female I...
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From
$321
Per Night
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1 / 32
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --128 Reviews on TRIPADVISOR Ranked #1 of 51 Specialty Lodging in Chicago! ************************* Beautiful & spacious--filled with charm and character! A Vintage Beauty With All the Modern Comforts & Amenities.... View all property information
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5 of 5 stars Reviewed July 26, 2014
What a perfect place for a family get away. The Clark Suite was perfect for our family of 7 adults. The kitchen was immaculate and well equipped with anything you needed. I...
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From
$80
Per Night
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1 / 14
Payment Protection
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Furnished Studio. Double bed, full bath, and full kitchen. Unique location. You don't need a car living here. Plenty of transit options. A couple of blocks to Red line train station. Direct express bus to Chicago downtown stops right around the corner. 20 minutes to the city center by public... View all property information
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4 of 5 stars Reviewed September 3, 2014
Great stay, close to the El train and cheaper than a hotel! Able to stay parked out front for free and take the El where ever we wanted to. If you want a great stuffed pizza...
5 of 5 stars Reviewed July 8, 2014
the location of the apartment we stayed was convenient enough:only some min away from the red line train and a min from the bus stop,so getting to downtown is easy.we got a great...
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From
$575
Per Night
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1 / 23
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
Details Reviews (17) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Spacious Bright Loft in the Heart of Everything Chicago 2 -10 adults, up to 12 with children Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Park home can be your home away from home in Chicago. Located in Chicago's newest neighborhood - 'SONO', at the... View all property information
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5 of 5 stars Reviewed November 24, 2014
We stayed during the Chicago marathon. The apartment is very conveniently located to the subway so that we could get everywhere we needed to during our stay. My favorite part of...
5 of 5 stars Reviewed November 24, 2014
My friends made all the arrangements on where to stay and they couldn't have picked a better place. I loved the location and the living space we had. I am not much of a writer...
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From
$250
Per Night
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West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
An Urban Oasis! This sophisticated end unit, 3-story townhome features exquisite mosaic, stone and marble thruout, island kitchen w/dark-stained cherry cabinets, imported granite and wallpaper, custom flooring/tiles. State-of-the-art Master BA w/Grohe fixtures, rain and steam w/multiple shower... View all property information
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3 of 5 stars Reviewed September 17, 2014
Nice place, only one bed and couldn't use the garage as advertised. Parking is a bit tricky, had to park several blocks away on Hubbard, but when rush hour ends it is good. No...
4 of 5 stars Reviewed July 10, 2014
This was a beautiful condo in a great location in Chicago. We rented the condo for one day for a video shoot and the couple renting it to us were so helpful and flexible with our...
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$100
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Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Nice and bright 2 bedroom 2 bath condominium two blocks from the lake and one block from train, bus, restaurants and coffee shops. Unit is cozy, spacious and conveniently located on first floor, with washer and dryer. Hardwood floors. LOCATION The unit is located on East Rogers Park, two blocks... View all property information
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From
$233
Per Night
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Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --133 Reviews Ranked #1 of 51 Specialty Lodging in Chicago! Walk in to the home and the first thing you notice is nothing has been taken for granted. You'll be engulfed in warm inviting hues. The beauty & integrity of... View all property information
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From
$165
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Lincoln Square
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Space Beautiful 2 Floor Duplexapartment near Foster and Damen on the North Side of Chicago. •3 bedrooms 2 Full Bathrooms •Full modern kitchen •Wireless internet •Cable with Smart TV have access to your Netflix and Hulu Accounts • Large Outdoor Deck w/ BBQ •Laundry in Unit The apartment... View all property information
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From
$100
Per Night
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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From
$100
Per Night
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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From
$175
Per Night
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1 / 22
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Enjoy all that Chicago has to offer and then come home and relax on the huge (20 x20) deck with the best skyline views in the city. This is a charming Condo in the perfect location. Have the neighborhood feel with dozens of great places to go for a bite to eat within a couple blocks, and also... View all property information
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From
$234
Per Night
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1 / 13
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This two queen room overlooks the city. The pillowtop bed and blackout drapes/curtains help ensure a restful night. The private bathroom has complimentary toiletries. Complimentary wireless Internet access keeps you connected, and the 37-inch plasma TV and iPod docking station are offered for your... View all property information
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From
$550
Per Night
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DePaul
4 Bedrooms, 4 Bathrooms, Sleeps 24
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Temporarily live in the best neighborhood in Chicago in an amazing Furnished Custom Single Family Home. This home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2 blocks to grocery stores, etc, etc. Everything you need is here! This is a top of the line... View all property information
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From
$74
Per Night
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Lincoln Park
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Wireless Internet Flat Screen TV in bedroom and living room Cable Clean sheets and towels Silverware, pots & pans Very large bedroom and living room Wall unit AC's in bedroom and living room Washer & Dryer is downstairs on first floor This is an ideal location for visitors. Nice restaurants... View all property information
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4 of 5 stars Reviewed January 18, 2015
This was our second time staying here. It is less than 5 minutes from our daughter's apartment. and the perfect Lincoln Park location. The apartment was clean, the bed...
4 of 5 stars Reviewed September 29, 2014
The unit is very nice: in a great neighborhood, within walking distance of a huge park, free (world class) zoo, free (world class) conservatory, and very nice business area full...
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From
$99
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Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This listing is for a private 2-bedroom apartment in the Rogers Park neighborhood of Chicago. The apartment is over 1200 square feet (111 sq meters) and has tall 9.5' ceilings (2.9 meters), a marble bath, and hardwood floors throughout. There is also a charmingly retro yet fully functional kitchen... View all property information
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5 of 5 stars Reviewed January 1, 2015
Lisa and Caitlin did such an amazing job making the home comfortable and I loved the books about Chicago and the Book they had made with so much helpful information! The location...
4 of 5 stars Reviewed October 2, 2014
Three of us stayed at at Devon property and were thrilled with the accommodations. The location to the local bus and train stops were very convenient. The hosts, Lisa and...
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From
$399
Per Night
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1 / 15
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3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (15) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Book Now for ALL INCLUSIVE BUDGET PACKAGE at a unique and beautifully decorated Bed & Breakfast inn. Stay on our third floor apartment with a shared bath and accommodations for up to 6-9 travelers - Full Size Refrigerator, Huge Leather Couch, Dinette Set, Massage Chair, Air Hockey Table and so... View all property information
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5 of 5 stars Reviewed April 13, 2013
We were visiting Chicago for accepted students' visit days at University of Chicago and wanted to stay somewhere close to the university that wasn't a Ramada Inn type hotel...
4 of 5 stars Reviewed December 7, 2012
We enjoyed our stay at Welcome Inn Manor B and B. Mel and his assistant were very hospitable, and always started our day off with a hearty and tasty breakfast. Mel is at the ready...
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From
$300
Per Night
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1 / 6
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Avenue. First Floor Condominium Unit, New Oak Floors, Granite Counters, Marble Baths. Stainless Steel Brand New Appliances. In Unit, Washer, Dryer. Three Large Bedrooms. Master Bath... View all property information
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5 of 5 stars Reviewed October 7, 2014
The condo is all that it is advertised. The neighborhood is quiet and the condo is well appointed with all of amenities for you to enjoy your stay. The hardwood floors are a nice...
5 of 5 stars Reviewed June 10, 2014
This condo fit our needs perfectly. My wife and I were staying with our young daughter and going to 3 Cubs games. It was great every night to be able to come back to this place...
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From
$125
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1 / 6
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2 Bedrooms, 1 Bathroom, Sleeps 3
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is an English Garden apartment...3 steps down... in an extra wide Greystone building, this charming two bedroom offers plenty of light, lots of closet space, hardwood floors and private entrance with vestibule & foyer... kitchen w/dishwasher & microwave. Fully furnished, utilities included... View all property information
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4 of 5 stars Reviewed August 17, 2014
I rented the garden unit of this house just north of Chicago. I was traveling with my 13-yr.old grandson and wanted separate bedrooms. The apartment was very clean and fully...
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From
$215
Per Night
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1 / 10
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3 Bedrooms, 1 Bathroom, Sleeps 5
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Just a quick walk to Chicago's Brown Line 'L'...take the train downtown...or to Wrigley Field (you can walk, too) from this North Center location. Comfy & inviting. Private entrance, private deck, plenty of space in this 3 bedroom unit. Updated kitchen, stainless Maytag appliances (built-in... View all property information
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5 of 5 stars Reviewed August 4, 2014
We had a wonderful stay on Belle Plaine Ave. Victoria was very accommodating to our needs and the apartment is beautiful. The neighborhood is also great, quiet but with walking...
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From
$265
Per Night
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1 / 9
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3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
3 Bedroom/1 Bath apartmentt located in the North Center neighborhood…Sleeps 6 Just 2 blocks from the train...A quick walk to Chicago's Brown Line 'L'...take the train downtown...or to Wrigley Field (you can walk, too) from this North Center location... Walk to everything...restaurants... Sola,... View all property information
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4 of 5 stars Reviewed July 3, 2014
Maison excellente !!!! Très propre, très fonctionnelle. Elle convient très bien pour être entre amis ou une famille. Clim, lave vaisselle, lave linge, sèche linge : tout est super...
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From
$205
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Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy this fabulous Chicago brownstone vacation rental located in the heart of the exclusive Gold Coast neighborhood. This downtown vacation rental gives you access to all the amazing features of downtown Chicago. Enjoy the shopping, eateries and entertainment that you can only find here. A... View all property information
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5 of 5 stars Reviewed September 28, 2014
Excellent contact with owner throughout the booking period and a good service overall. Really liked this old Brownstone building. The apartment was spacious, comfortable and...
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Lakeview
Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Housekeeping...
  • Internet Access
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Hello, we are currently looking to FLIPKEY our studio for the month of December and January 2015. This particular unit is on the 9th floor with phenomenal city views. The building's location is off of Belmont and Broadway. 500 West Belmont is a modern, elevator-equipped 9-story apartment building... View all property information
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Chicago Vacation Rentals

Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!

Chicago family vacations

Chicago is a great city for families and a vacation home rental makes it easy to explore all that the second city has to offer. If it’s baseball season, catch a Chicago Cubs game at historic Wrigley Field, one of the oldest ball parks in the country. Or take the kids out to Navy Pier, which features amusement rides, shops and restaurants right on Lake Michigan. If you’re kids are animal lovers, visit the Great Ape House at the Lincoln Park Zoo, where admission is still free. Or see dinosaurs at The Field Museum of Natural History.

Chicago attractions

There's plenty to do in Chicago and a vacation rental in the city will put you within walking distance of most of the city's many attractions. Art lovers will enjoy the Art Institute of Chicago where they can browse the large collection of impressionist and post-impressionist paintings before heading to the newer Modern Wing. After, you’ll want to head over to nearby Millennium Park, which features public art and cultural events year-round. During the warmer months, find a spot on the sand at Oak Street Beach, a great place to people watch with views of downtown skyscrapers and Lake Michigan.

Chicago day trips

For those who want to explore Chicago beyond the city center, there are plenty of short getaways worth exploring, all within an hour or two of your vacation rental. Nearby Oak Park is home to the Frank Lloyd Wright Home and Studio. It’s also the birthplace of Ernest Hemingway. For those looking for outdoor adventure, head south to Starved Rock State Park where you can hike miles of trails through rolling hills or go fishing, boating or horseback riding. Other popular getaways include Lake Geneva in southern Wisconsin or the shores along Lake Michigan outside the city.

Saving money on Chicago vacation rentals

Whether you want to stay in a chic downtown apartment rental in Chicago or a spacious house in the suburbs, we can help you find a deal that fits your budget. There are discounts on every type of property to help you get the most bang for your buck.