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Vacation Rentals in Chicago, IL

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From
$85
Per Night
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1 / 14
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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From
$195
Per Night
View Details
1 / 15
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
From
$89
Per Night
View Details
1 / 7
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
From
$79
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
$197
Per Night
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1 / 7
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two bedrooms, two bathrooms condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 8 people. FREE Wireless internet access. FREE parking on public street in front of the building.... View all property information
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From
$79
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
$140
Per Night
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1 / 48
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Southwest Side
2 Bedrooms, 1 Bathroom, Sleeps 6
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
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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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From
$140
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
Make Inquiry
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
$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
$167
Per Night
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1 / 13
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two bedrooms, one bathroom condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 8 people. FREE Wireless internet access. FREE parking on public street in front of the building. Bus... 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
$80
Per Night
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1 / 6
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
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
$275
Per Night
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1 / 9
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 5
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • 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
The Aster House has been a legitimate business since 1891 (!) and under the present owners since1982. We've had several tenants stay as long as 9 years and return for as long as 18 years, so you may be assured of a secure and comfortable stay! TRANSPORTATION: We're 1/2 to 1 block from the... View all property information
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From
$149
Per Night
View Details
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
$200
Per Night
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1 / 8
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This very affordable two bedroom, two bathroom apartment can sleep up to six guests. There are queen sized beds in each bedroom and a pull out couch in the living room. With features including: a breakfast table in the well-appointed kitchen; dining room; comfortable living room; a balcony;... View all property information
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5 of 5 stars Reviewed August 17, 2014
Nice apartment for up to 6 people, around $20 taxi ride from the Airport. Close to a large park, bus, and train stations. We purchased 7 days CTS passes for $33 each with...
4 of 5 stars Reviewed March 29, 2014
Bed was a little uncomfortable and broke often. Parking was difficult. Clean apartment, ideal for a large family
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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
$159
Per Night
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1 / 11
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Roscoe Village
2 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
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
$80
Per Night
View Details
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
$250
Per Night
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1 / 14
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West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (3) Make Inquiry
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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From
$99
Per Night
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1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Hello and thank you for viewing my listing. I have a fully furnished two bedroom, one bath apartment available for your upcoming trip to Chicago. The neighborhood is located on them city's far West side. For easy, hassle-free transportation to the downtown area look for tube Metra station a mere... View all property information
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From
$199
Per Night
View Details
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
$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
$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
$120
Per Night
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1 / 23
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
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
$766
Per Night
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1 / 49
Lakeview
11 Bedrooms, 6 Bathrooms, Sleeps 21
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Looking for Space? You've Come to the Right Place! The Lakewood Avenue property has three apartments in the building offering plenty of space for your larger gathering while at the same time providing some privacy when you need those 'alone' times! 10 Bedrooms (13 beds) & 6 Bathrooms total--Sleeps... View all property information
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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
$325
Per Night
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1 / 23
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 8
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
Amazing spacious, bright and sunny loft in Lincoln Park at the crossroads of everything. This 2/3 bedroom two full bath former magic card factory has been renovated into an oversized two bedroom plus connected den that very comfortably sleeps up to 7 guests in real beds with plenty of dining and... 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
$150
Per Night
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1 / 13
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The Loop
Studio, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Downtown apartment with great location, views and furnishings. Large convertible studio with views of Lake Michigan and Navy Pier. Luxurious memory foam king size bed, queen size high end futon sofa, full kitchen and bath. It is a studio, so it is perfect for 2 people and a 3rd or 2 children on... View all property information
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4 of 5 stars Reviewed October 25, 2014
Had great time staying here, awesome views of the lake and Navy Pier. Easily can walk to restaurants, attractions, shopping, and parks. Great place to stay.
5 of 5 stars Reviewed September 30, 2014
Very Confortable apartment. NIce neighborhood. Good location a few blocks from Millennium Park, Navy Pier and Downtown Chicago. Excellent lake view.
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From
$250
Per Night
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1 / 14
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
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
$300
Per Night
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1 / 6
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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
$300
Per Night
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1 / 8
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
An 1890's vintage walk-up in the heart of Gold Coast where Chicago's elite reside - centrally located downtown is an updated one bedroom, one bathroom has everything you need outside the front door...enjoy coffee every morning in the park at Whisper's Cafe, spend the day shopping on Michigan Avenue... View all property information
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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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$120
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Lincoln Park
1 Bedroom, 1 Bathroom, Sleeps 3
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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 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...
5 of 5 stars Reviewed August 24, 2014
Vintage Chicago apartment. Really spacious. Everything you need is there: just bring your clothes and toiletries! Can't get a more convenient location. Nice owners to work with...
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$258
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago. Located on the Magnificent Mile. Industry and creativity converge in Chicago, the birthplace of the... View all property information
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5 of 5 stars Reviewed December 2, 2014
For downtown Chicago stay, this was fantastic...lots of room and great location! We were a walk away from anything...from Navy Pier to the beach to shopping to family museums. A...
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$140
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Northwest Side
3 Bedrooms, 1 Bathroom, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
We created this new construction apartment to fit our family as a second home. We live in Arkansas but are from Chicago with friends and family all here. When we visit it is perfect for our family of 5 with a crib, bunk bed, and queen bed. The apartment is right off of both major highways, 90... View all property information
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$99
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Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
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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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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...
4 of 5 stars Reviewed September 3, 2014
Stayed here with a few friends for the weekend. Had a great time, The location is perfect, its close to everything, yet still residential. Lisa was the main contact, she was...
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$140
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Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 3
Booking
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
I've lived here for six years and it keeps getting better and better. We're located in Streeterville (downtown Chicago). The building is just two blocks from Lake Michigan (beaches, parks, bike trails), two blocks from Michigan Ave (endless shopping), and is about a three min. walk to Navy Pier.... View all property information
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5 of 5 stars Reviewed June 20, 2014
Brooks was a pleasure to deal with and his apartment is great. He was super easy to deal with during the booking process, stopped by on our arrival and made clear he was there if...
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From
$145
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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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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$120
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Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
I've lived in the building for 6 years and it keeps getting better and better. We're located in Streeterville (downtown Chicago). The building is just two blocks from Lake Michigan (beaches, parks, bike trails), two blocks from Michigan Ave (endless shopping), and is about a three min. walk to Navy... View all property information
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5 of 5 stars Reviewed November 15, 2014
We had a wonderful time at Brooks's "Urban Oasis". It is well located to see everything around Chicago city. Friendly helpful doormen/women, secure access, great facilities...
5 of 5 stars Reviewed November 15, 2014
Why was staying at Brook's make your trip to Chicago so special: * Immaculate condo with all your comfort needs *Close to everything -Really! *We felt so very comfortable and...
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From
$280
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Lakeview
3 Bedrooms, 1 Bathroom, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Safe
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Hey, I have a great apartment available in one of the safest area in Chicago,Wrigleyville! My place is very clean, comfortable and a great fit for you! This unit is in a great location rigth across from wrigley field! It is furnished with nice furniture. A great living room that is very cozy... View all property information
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From
$350
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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
  • ?
  • ?
About this property
This is a beautiful high end building and modernly furnished condo in the heart of River North that can accommodate up to six people. 2 bedrooms with queen sized beds and 2 bathrooms, plus a huge sectional couch with a fully equipped kitchen. View all property information
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$275
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
This is another one of our properties in the South Loop that has amazing amenities and a great feel to it. You will see from the pictures there is a king sized bed along with a sleeper sofa in the loving room which is how this unit can accommodate four people. Please let me know what questions you... View all property information
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$99
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2 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This is a house and the main floor is occupied by other guests. You WILL NOT have the house to yourself.... ONLY the entire top floor of the house will be reserved for you as a private room. I DO NOT accept Chicago Residents. THIS ad is for entire Newly Renovated Attic Space/ floor as a private... View all property information
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From
$225
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Spacious, elegantly appointed and furnished Lakeview vacation/executive two bedroom, one bathroom apartment. First floor on a quiet tree-lined street, the entire apartment features; either oak floors or ceramic tiles, all solid oak doors and windows and oriental rugs. You will find our... View all property information
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4 of 5 stars Reviewed July 28, 2014
Close to transit & grocery. Lots of space. Communication with Andy was great. He answered any questions we had before the trip in a timely manner. Easy check in and out...
4 of 5 stars Reviewed July 2, 2014
The house was great, clean and comfortable with everything we needed. The neighborhood was great and walking distance to Wrigley Field. The train was close as well. The only down...
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$234
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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
$95
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1 / 10
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Lakeview
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a beautiful garden unit. It comes fully furnished with a queen size bed plus a pull-out couch. Plenty of sitting room, updated bathroom, does not have kitchen but does have small fridge, microwave and coffee maker. The location is ideal, being close to the city and still in a quiet... View all property information
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5 of 5 stars Reviewed October 13, 2014
My wife and I spent 3 night here in Sept 2014. The owner was very friendly and helpful. This studio is located in a nice quiet neighborhood, close to restaurants and shops, and...
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From
$90
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Charming, roomy one bedroom , with open kitchen and living space. This recently refurbished loft-style apartment gives visitors to Chicago a chance to visit and explore whist enjoying the comforts of modern living. Hardwood floor, and ceramic tiles in kitchen and bathroom. Plenty of sitting... View all property information
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4 of 5 stars Reviewed September 16, 2014
The accommodations were not real fancy but well suited for a busy stay in Chicago! Excellent location for the price. Wrigley and other top sites are easily accessible. If you are...
3 of 5 stars Reviewed June 15, 2014
Ok so if you're expecting a pretty little getaway in Chicago with views and a location then this place isn't for you. The apartment is located atop of a commercial building that's...
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From
$150
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1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Large, roomy two bedroom loft like apartment tastefully appointed and furnished. Hardwood floors and ceramic tiles in kitchen and bathroom. Plenty of sitting room with large screen TV, fireplace and free WiFi. Two full bedrooms, one with a king sized and the other with a queen sized bed. You... View all property information
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$99
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Rogers Park
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
The Ashland Arms Guest House is an adult urban bed-and-breakfast. We offer five themed rooms; Sports, Dream, Gear, Bunk and Leather. These open up to our generously appointed soft-loft Great Room featuring a comfortable and inviting communal kitchen/dining/living room. Continental breakfast is... View all property information
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From
$7,000
Per Month
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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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.