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Vacation Rentals in Chicago, IL

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From
$79
Per Night
1 / 14
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Northwest Side
Studio, 1 Bathroom, Sleeps 2
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From
$95
Per Night
1 / 11
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Lincoln Square
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (1) Make Inquiry
From
$99
Per Night
1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
From
$159
Per Night
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
$250
Per Night
1 / 15
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Housekeeping...
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and clubs with-in walking distance. Try a different ethnic specialty every night of the week. The apartment is in an ideal location to come and explore Chicago. Stroll 2 blocks through... View all property information
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From
$233
Per Night
1 / 28
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Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
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! ************************************************************************************************ A Vintage Beauty With All the Modern Comforts &... View all property information
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From
$197
Per Night
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
  • Housekeeping...
  • 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
$99
Per Night
1 / 28
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Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden or Yard
  • 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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From
$250
Per Night
1 / 15
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Near North Side
1 Bedroom, 2 Bathrooms, Sleeps 3
Bookings
Details Reviews (3) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
With 42 stories of sleek modern architecture, Optima Downtown is the place to stay while you're in Chicago. Located only 1 block from the world famous Michigan Ave, this 1 bedroom is located directly in the heart of Downtown. In this modern building you'll enjoy: -Prime location in Chicago... View all property information
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3 of 5 stars Reviewed October 24, 2014
The apartment was in a great location. However the kitchen was not clean. When I opened a drawer to see the contents, I found two pans with dried on food. One had food an inch...
4 of 5 stars Reviewed September 7, 2014
Great location, hard to find it's on upper Illinois...parking expensive, use spothero and find a better place to park, lousy housekeeping, dirty dishes in dishwasher, no linens...
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From
$65
Per Night
1 / 40
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The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
888.761.RENT or 312.242.1625 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) Check Availability and Book Online Now: http://reservation.worldweb.com/hotel/1278... View all property information
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5 of 5 stars Reviewed July 19, 2014
Beautiful furnished apartments with kitchennete and in the heart of downtown, just a few blocks away from State st and michigan ave. I had a very pleasant and comfortable stay...
5 of 5 stars Reviewed May 7, 2014
The location is so convenient, the blue line train from O'hare airport takes you right to the stop of which is about 5 minutes walk to the building. The unit is clean and with...
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From
$75
Per Night
1 / 16
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (31) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
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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...
5 of 5 stars Reviewed November 7, 2014
I visit my son often and have stayed in other condos and hotels all throughout the city and this by far is the best. With dorm style amenities and generous snacks, it's better...
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From
$199
Per Night
1 / 9
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our 1 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic Mattresses, Cleaning Service... View all property information
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4 of 5 stars Reviewed September 29, 2014
The apartment was more spacious and comfty than it appeared in photos. The location was excellent, we had everything we could need at much 2 blocks away (restaurants, bars...
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From
$135
Per Night
1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
High rise apartment: Downtown Chicago. Walking distance most attractions. Close to public transportation One bedroom apartments available for short term or extended stay. View all property information
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4 of 5 stars Reviewed August 18, 2014
Very strategic location near to major attractions. Very spacious and quiet. The best coffee is just down the building! The only thing was the wifi was extremely slow, me and my...
3 of 5 stars Reviewed July 1, 2014
security was not aware of our check in and had to call and verify. kitchen is not adequately stocked for those who may use knives, forks and wine glasses. it was, however...
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From
$80
Per Night
1 / 14
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Washer
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
$425
Per Night
1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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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From
$85
Per Night
1 / 14
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Garden or Yard
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This is a nice place on a quiet street, close to transportation and many restaurants. Very close to I 94. View all property information
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5 of 5 stars Reviewed September 20, 2014
Hanne was very easy to work with and extremely nice. Nice roomy apt and pretty close to everything. I would definitely stay here again when traveling to Chicago. Very quiet...
5 of 5 stars Reviewed September 11, 2014
Roomy 2 bedroom was in walking distance to great bars and restaurants and was a ten minute drive to many "Lincoln Park" area attractions such as the zoo, aquarium and...
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From
$140
Per Night
1 / 49
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Southwest Side
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (30) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
We have two really incredible vacation rental apartments. We are offering great special off season rates for our Winter Months through March. These specials range from $110 per night to $195 per night and as low as $875 per week.. The best rates are for longer rentals and some dates will have... View all property information
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5 of 5 stars Reviewed November 13, 2014
Our family of four had an excellent time at this apartment. Bob was very easy to deal with and extremely helpful. Key code access to the apartment was very convenient. A garage...
4 of 5 stars Reviewed September 27, 2014
We were very pleased with our stay at this facility. It isn't in the typical touristy area which we liked as it made our urban experience feel more authentic and any neighbors we...
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From
$140
Per Night
1 / 48
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Southwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (13) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
We have two really incredible vacation rental apartments. We are offering great special off season rates for our Winter Months through March. These specials range from $110 per night to $195 per night and as low as $875 per week.. The best rates are for longer rentals and some dates will have... View all property information
Make Inquiry
5 of 5 stars Reviewed April 7, 2014
Our family of four (two teens) spent 5 days here during spring break and had an excellent experience. We went downtown every day by catching the red line train at the 35th/Sox...
5 of 5 stars Reviewed May 2, 2012
We couldn’t be more pleased with our stay, everyone had a fantastic time. Our visit took place April 12-15 and there were six of us; my parents (early 50’s), younger brother and...
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From
$89
Per Night
1 / 7
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden or Yard
  • Housekeeping...
  • 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
$175
Per Night
1 / 4
Payment Protection
Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Great Old Town 2BR. Very homey and well suited for travelers on business or leisure. Steps away from all public transportation in a area with gorgeous tree lined streets and high end accommodations. The Space Welcome to my 2 bedroom fully furnished “Old Town Chicago” condo. Inside there... View all property information
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4 of 5 stars Reviewed August 18, 2014
I stayed at this apartment for 6 nights in August together with my wife and my two kids. The apartment was big enough for all of us and had almost everything that we needed. The...
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From
$199
Per Night
1 / 15
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Garden or Yard
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our 1 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic Mattresses, Cleaning Service... View all property information
Make Inquiry
4 of 5 stars Reviewed September 20, 2012
We rented a one-bedroom apartment in this six-apartment building for the entire summer, so we could experience Chicago without exhausting ourselves. Cozy apartment, comfortably...
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From
$120
Per Night
1 / 26
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Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
  • Shared Outdoor Pool...
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
$140
Per Night
1 / 19
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Gold Coast, Near North Side
Studio, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • 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 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
$199
Per Night
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
  • Garden or Yard
  • Grill
  • Hot Tub
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
$200
Per Night
1 / 16
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Hot Tub
  • Internet Access
  • Private Pool
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Enjoy unbelievable waterfront and city views from your 37th floor corner unit with floor-to-ceiling windows. This designer suite is 3X larger than a typical Marriott King room and will be your home away from home. Start you Chicago experience here Luxury high rise between the Loop & River with... View all property information
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From
$115
Per Night
1 / 23
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Northwest Side, Wicker Park / Bucktown
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Housekeeping...
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Chicago Bathhouse Corporate Residences are located on the 2nd floor of a 2 story building in Wicker Park Chicago. This vacation rentals are 2 bedrooms, 1 bathroom, 10 minutes from Chicago downtown. View all property information
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2 of 5 stars Reviewed October 14, 2014
I felt like I was being punked! When I booked this place it advertised access to the spa at the bath house. When we arrived the curt "receptionist" said access was only for one...
3 of 5 stars Reviewed June 15, 2014
This apartment in Wicker Park is enormous and very nice! It's in a pretty sweet location above a bathhouse and next to a great breakfast place called Milk & Honey. The el is about...
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From
$100
Per Night
1 / 14
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Garden or Yard
  • 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
$167
Per Night
1 / 13
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Housekeeping...
  • 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
1 / 8
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DePaul
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Housekeeping...
  • Internet Access
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
$450
Per Night
1 / 19
Payment Protection
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Newest Luxury Residential High Rise in the Heart of Downtown Chicago, Right off the Magnificent Mile! The Space A Modern 2 Bed 2 Bath Condo Located In The Heart Of Downtown Chicago Right Off The Magnificent Mile In this modern building you'll enjoy: -Prime location in Chicago right off of... View all property information
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From
$195
Per Night
1 / 10
Payment Protection
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
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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$199
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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
  • Garden or Yard
  • 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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$165
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1 / 22
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Lincoln Square
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • 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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$169
Per Night
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
$500
Per Night
1 / 10
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The Loop
2 Bedrooms, 1 Bathroom, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Modern luxury One bedroom with queen size bed Location, Location, Location Hotel type amenities. Queen size bed in your private room 900 square feet space Sleeps 4 Flatscreen TV in the livingroom Wireless Internet is not available Clean freshly-washed white sheets and white Towels waiting for... View all property information
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$100
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1 / 20
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
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  • Air Conditioning
  • Dishwasher
  • Garden or Yard
  • 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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$120
Per Night
1 / 23
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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
  • 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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$110
Per Night
1 / 7
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Garden or Yard
  • 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
$249
Per Night
1 / 17
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Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Experience our 2 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service Included,... View all property information
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From
$160
Per Night
1 / 19
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Optima is a new building opening in Spring of 2013, towering 42 stories over Michigan Avenue. Sleek design incorporates floor-to-ceiling reflective glass windows and European-designed finishes throughout. The condo features 700 sq. ft. of bamboo flooring, porcelain tile, granite counter tops,... View all property information
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5 of 5 stars Reviewed April 12, 2014
This modern apartment really is 1 minute walk from the mag mile, next door to Inter Continental Hotel (try the wine tasting menu!) also has lake views. A well equipped gym and...
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From
$80
Per Night
1 / 18
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Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Nice and bright 2 bedroom 2 bath condominium two blocks from the lake and one block from train, bus, restaurants and coffee shops. Unit is cozy, spacious and conveniently located on first floor, with washer and dryer. Hardwood floors. LOCATION The unit is located on East Rogers Park, two blocks... View all property information
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From
$159
Per Night
1 / 7
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Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Fireplace
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our amazing, over sized, fully furnished “Old Town Chicago” studio with private balcony designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Tempur-Pedic... View all property information
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From
$275
Per Night
1 / 9
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DePaul
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Garden or Yard
  • Grill
  • Housekeeping...
  • Internet Access
  • Safe
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
$1,000
Per Week
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
$200
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1 / 34
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (6) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
With 42 stories of sleek modern architecture, Optima Downtown is the place to stay while you're in Chicago. Located only 1 block from the world famous Michigan Ave, this 1 bedroom is located directly in the heart of Downtown. In this modern building you'll enjoy: -Prime location in Chicago... View all property information
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5 of 5 stars Reviewed April 29, 2014
My wife and I were in Chicago for the 100th anniversary of Wrigley Field. The apartment was spotless upon arrival. Alvin was gracious and more than asccommodating. Great public...
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$299
Per Night
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Welcome to Chicago -- far from your typical Chicago rental. The building offers unparalleled amenities, upscale stylish accommodations, and floor-to-ceiling dynamic views of the Chicago skyline. This property is unlike any other in its class and the experience is definitely one-of-a-kind.... View all property information
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5 of 5 stars Reviewed October 21, 2014
El departamento está mucho mejor de lo que se ven en las fotos y vale la pena cada centavo que pagamos por él. Además de la excelente ubicación (está a una cuadra de la avenida...
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$200
Per Night
1 / 8
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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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
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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$120
Per Night
1 / 7
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Lincoln Park
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
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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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$400
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1 / 18
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Lakeview
3 Bedrooms, 1 Bathroom, Sleeps 8
Booking
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Great 3 Bedroom unit located in the heart of Wrigleyville, walking distance to Wrigley Field, restaurants, bars and all that Wrigleyville has to offer!!!! The Red Line Train, which is the main train line in Chicago is only 2 blocks away. 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.