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Vacation Rentals in Chicago, IL

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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
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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
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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
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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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$120
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1 / 48
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Southwest Side
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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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
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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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$321
Per Night
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1 / 32
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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$125
Per Night
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1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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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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$99
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1 / 7
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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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
$222
Per Night
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1 / 26
Lakeview
3 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Intimate & cozy and filled with character! You'll be so comfortable you'll never want to leave! 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 the historic Greystone recaptured;... View all property information
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$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
$80
Per Night
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1 / 6
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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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
$1,000
Per Week
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1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 3
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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
$65
Per Night
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1 / 12
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Northwest Side
Studio, 1 Bathroom, Sleeps 2
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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
$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
$275
Per Night
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1 / 10
The Loop
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
30 Day Minimum Rental Beautiful natural light pours into this spacious 4-bedroom Lincoln Park vacation rental. Host friends with a beautiful kitchen, or step out into the heart of a famous Chicago neighborhood. Out your door you'll find micro-brews at Atlas Brewing Company, deep dish pizza at... 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
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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
$395
Per Night
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1 / 8
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DePaul
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
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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
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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
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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
$129
Per Night
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1 / 13
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Lakeview
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This beautifully updated 1 Bedroom, 1 Bathroom loft in Lakeview has all you'll need during your stay in Chicago! Conveniently located only 1 block from the lake shore, only 3 blocks from Wrigley Field, & close downtown, shopping, dining and more! Lakeview is one of the hearts of Chicago. The unit... View all property information
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From
$99
Per Night
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1 / 20
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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
$205
Per Night
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1 / 12
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Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
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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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$205
Per Night
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1 / 12
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Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
First Class Chicago vacation rentals by owner gives you the loveliest choice in Chicago Brownstone vacation rentals. Located in the Gold Coast neighborhood, these brownstones will surpass your expectations for quality and comfort. You will never want for a Magnificent Mile hotel as First Class... View all property information
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From
$80
Per Night
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1 / 14
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Studio, 1 Bathroom, Sleeps 2
Bookings
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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
$350
Per Night
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1 / 33
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
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Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ping Pong Table
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Unit not available for daily rental in July 4th Holiday ! *Prices may vary depending on the season. Premium months are between April and September. *Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay. Michigan Avenue at 21st street 2BR /... View all property information
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From
$305
Per Night
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1 / 12
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Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Apartment - 2 Bedrooms + Convertible bed(s) - 2 Baths - (Sleeps 4-8) Another First Class Chicago property! City of Chicago Vacation Rental License #2125365. Rent Legally! You've found it! Location, Location, Location! An historic 1890's brownstone in the heart of the exclusive Gold Coast where... View all property information
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2 of 5 stars Reviewed August 24, 2014
I waited a while to write this review to ensure it gave the landlord a chance to answer some of the issues that I had with this property however after 3 weeks I have still...
1 of 5 stars Reviewed May 12, 2014
We had very high hopes for a First Class stay during our four-day trip to Chicago over Easter at the 2-bedroom unit in the Gold Coast area to celebrate two special occasions...
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From
$165
Per Night
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1 / 22
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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
$169
Per Night
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1 / 16
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Lakeview
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This is a spacious 1 bedroom 1 bath that hosts large windows and updated appliances with comfortable shabby chic decor. The apartment is located in the center of it all in the lively neighborhood of Lakeview, bordering Lincoln Park. There are tons of restaurants and activities within a few blocks,... View all property information
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From
$550
Per Night
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1 / 18
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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
$150
Per Night
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1 / 14
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Housekeeping...
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!! ASK ABOUT OUR PRICE MATCHING OPTION!! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. -3 Bedrooms -2 Bathroom -Hardwood Floors -Tiled Bathroom -Centrally controlled Heat and Air -Big back yard... 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
$69
Per Night
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1 / 7
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Lincoln Park
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (2) 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
Per Night
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1 / 28
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Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (5) Make Inquiry
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
$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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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
Make our apartment the perfect home base for your family vacation or romantic getaway to Chicago. There is plenty of room to spread out and enjoy yourselves. The house is beautifully furnished and stocked with all of the essentials. The apartment is an easy walk to multiple bus and train lines,... View all property information
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5 of 5 stars Reviewed September 25, 2014
My wife and I travel to Chicago 4-6 times per year to visit our daughter and her family. We usually stay with her but this time she hosted her sister and their family which made...
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From
$234
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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
$75
Per Night
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1 / 16
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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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
$575
Per Night
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1 / 23
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3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
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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
$149
Per Night
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1 / 16
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located a block north of the Chicago River this property features a prime location just steps from Michigan Avenue. Amenities include gym, pool, and hot tub. Two queen size beds and a fold out sleeper sofa make it possible to sleep six. Chicago's premier downtown Streeterville neighborhood grants... View all property information
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From
$100
Per Night
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1 / 18
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Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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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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1 / 1
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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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From
$300
Per Night
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1 / 14
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Brilliantly sunny top floor of historic two flat on a lovely tree lined street. The well appointed apartment is beautiful. It has been furnished very thoughtfully, with comfort and simplicity in mind - It boasts of old world charm along with modern conveniences. Steps away from the quaint... 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
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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
$100
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1 / 20
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
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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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1 / 14
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
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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
$350
Per Night
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1 / 13
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (15) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Modern 2 Bedroom Apartment walking distance to Wrigley Field and the Blue Line. Beautiful Place and Great Location! The apartment comes with anything you could want. -A full kitchen, with all brand new appliances. -A brand new queen sized bed with box spring, and an ultra modern bathroom... View all property information
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From
$200
Per Night
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1 / 14
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Tides is a great way to experience life and culture in the heart of Chicago! Featuring a modern contemporary feel, the short term rentals at The Tides offer dramatic finishes including tiled entries, granite islands and cherry cabinetry, open floor plans with captivating views from the... View all property information
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From
$125
Per Night
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1 / 6
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This unit sleeps up to 4(four) guests maximum... I have additional units if you need more beds!! Please be sure to view my other units: Please view my other units: #2936706, #2936829, #2937555, #2936763 and #2937588...hope to see you soon! Bright and inviting…large 1 bedroom in LINCOLN SQUARE.... View all property information
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From
$225
Per Night
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1 / 9
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Details 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
Gracious duplex with comforts of home. This unit has 1 full bath on upstairs level and a powder room on the main level. Fully equipped eat in kitchen with breakfast bar. Cable, wireless internet. Convenience is Key! A quick walk to Chicago's Brown Line 'L'...take the train downtown...or to... View all property information
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From
$145
Per Night
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1 / 28
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Newly built! Sleeps comfortable 4. Conveniently located steps from the from train station! Elevator and top floor. Attached indoor parking garage included for no add'l charge. ***BEFORE ACCEPTING*** NO PARTIES and noise level must be keep to a minimum as this is a residential place with neighbors.... View all property information
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5 of 5 stars Reviewed August 26, 2014
This was a very nice condo in great condition and is very clean and comfortable. The owner was very helpful and pleasant. The location was super with the Brown "L" Train being...
4 of 5 stars Reviewed July 2, 2014
The apartment is very well located, very close to buses and the train station. It is very well maintained and nicely furnished. The bedroom is small but very comfortable. The...
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From
$7,000
Per Month
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1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Optima Chicago sits directly behind the famed Intercontinental Hotel on Michigan Avenue. In addition to it's amazing location, this condo boasts massive views of Lake Michigan and a roof-top hot tub overlooking the entire city of Chicago! 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.