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Apartment Rentals and Condos in Chicago, IL

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    Travelers to Chicago are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 29
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 21
    5 of 5 bubbles (3) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 21
    5 of 5 bubbles (3) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 6
    5 of 5 bubbles (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Chicago, Illinois 60613
    5 of 5 bubbles 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 bubbles Reviewed April 28, 2014
    This condo was wonderful. It was clean , modern and very spacious. It is at the end of a quiet street so there was no noise. It is right by Lincoln Park and it was very easy to...
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    1 / 56
    5 of 5 bubbles (42) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    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
    Location Information
    Chicago, Illinois 60618
    5 of 5 bubbles Reviewed 3 weeks ago
    Tiendas cercanas, a 20 minutos del centro de Chicago. Recomendable. ... Many thanks hanne for your hospitality, we really enjoyed staying in your apartment.
    5 of 5 bubbles Reviewed 4 weeks ago
    The apartment is very nice and comfortable. The place is close to the Belmont metro station (the Blue Line connects directly with O´Hare and downtown). The owners are very...
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    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!!<BR><BR>ASK ABOUT OUR PRICE MATCHING OPTION!!<BR><BR>Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people.<BR><BR>-3 Bedrooms<BR><BR>-2 Bathroom<BR><BR>-Hardwood Floors<BR><BR>-Tiled Bathroom<BR><BR>-Centrally... View all property information
    Location Information
    Chicago, Illinois 60162
    5 of 5 bubbles Reviewed November 17, 2015
    The house was very nice modern and clean. The area is quite. I would recommend staying here. They were very accommodating. Would stay here again in the future.
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    1 / 8
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • x
    About this property
    .One of three spacious apartments in a multi-flat historic building, located in the true artist oriented neighborhood in the heart of Chicago. Large kitchen space and a full newly remodeled bath with Jacuzzi tub and beautiful Moroccan tile. Cozy dinning room and sunny living room each with... View all property information
    Location Information
    Chicago, Illinois 60608
    4 of 5 bubbles Reviewed August 29, 2016
    The apartment is lovely and huge. It was a pleasure to stay there. The neighborhood was friendly and fascinating. We were too busy to use the tv or internet so I can't say...
    5 of 5 bubbles Reviewed July 12, 2016
    Would reccomend! The apartment was much bigger than I had expected. The pictures did not do it justice. Amanda was a wonderful host. We had a great time!
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    1 / 27
    4.5 of 5 bubbles (6) Very good
    Near South Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    1 KING SIZE Bed in the masteroom and 1 full size bed in the second and air-mattress available for more than 5 people 1600 square feet Sleeps 6 2 Flatscreen TVs Clean freshly-washed white sheets and white Towels waiting for you. Coffee maker now available. Private garage parking in the... View all property information
    Location Information
    Chicago, Illinois 60606
    4 of 5 bubbles Reviewed May 29, 2015
    I actually rented this place for the "bike the drive" cycle ride over Memorial Day. The pictures are accurate. Tee was always available for questions, checking in, etc. a short...
    5 of 5 bubbles Reviewed November 7, 2014
    The Condo was a great place for rest and relaxation between all the excitement we found in Chicago. Outstanding views of the Chicago skyline, great location, comfortable beds and...
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    1 / 32
    5 of 5 bubbles (4) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR>Welcome to the LEX... View all property information
    Location Information
    Chicago, Illinois 60616
    5 of 5 bubbles Reviewed November 5, 2014
    The apartment was great! The hosts were very easy to contact when needed. Even the neighbours were friendly. Good location, away from the busy city Central but still close enough...
    5 of 5 bubbles Reviewed October 29, 2014
    21st and Michigan, right on the bus route to go to the Downtown core and to get to the museums. Just blocks away from Chinatown. Market just across the street for meat and eggs...
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    1 / 10
    5 of 5 bubbles (3) Excellent
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
    Location Information
    Chicago, Illinois 60618
    5 of 5 bubbles Reviewed July 4, 2016
    Very clean, modern, and responsive owner. It is located in a nice neighborhood that is close to public transportation.
    5 of 5 bubbles Reviewed August 7, 2015
    We needed a place to stay in Chicago close to family. This rental was perfect. There was more than enough room for 5 of us. It was extremely clean and very nicely decorated...
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    1 / 15
    4.5 of 5 bubbles (3) Very good
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Brand New Renovation, Hardwood floors Throughout , New fully stocked Kitchen and brand new Bath. Leave your troubles behind and escape to a clean, Modern, Cozy and Comfortable Apartment. We have Fresh Linens, Clean Towels, coffee and tea as well as everything you need to cook for a longer stay.... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 bubbles Reviewed August 31, 2016
    Our host was so accommodating to all our needs. Didn't not have to call them with any issues. The location was perfect for us. We would recommend this listing to friends and/or...
    4 of 5 bubbles Reviewed April 4, 2016
    Pros: Ideal for 1-2 people traveling. I think there's an inflatable mattress or something to set up in living room for more. Nicely updated apartment. Walk to Wrigley...
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    1 / 11
    4.5 of 5 bubbles (2) Very good
    Northwest Side
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Hello and thank you viewing my condo's listing. My name is Bogdan and I am the property owner of this duplex. I'm a business professional and proud Chicagoan. If you are looking for comfortable, clean and modern accommodations, you've come to the right place. <BR><BR>My duplex is located in the... View all property information
    Location Information
    Chicago, Illinois 60647
    4 of 5 bubbles Reviewed July 26, 2016
    This house in the Humboldt Park section of Chicago was a bargain. It's very spacious -- many bedrooms on 2 levels, sleeping about 10 people. LOADS of room. Never having visited...
    5 of 5 bubbles Reviewed May 5, 2016
    Such a fantastic space!! Originally we were to have 10 people in our group for the weekend, but after unexpected cancelations we were down to six or less. The space could easily...
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    1 / 7
    4.5 of 5 bubbles (12) Very good
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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
    Location Information
    Chicago, Illinois 60614
    5 of 5 bubbles Reviewed 4 weeks ago
    The flat was great, keys in place to be picked up when we arrived and all spotless. We appreciated coffee available too in the cooler.
    5 of 5 bubbles Reviewed October 5, 2016
    Worked great for a quick night in the city. Girlfriend loved that the zoo was within walking distance and everything else was a short cab/Uber trip away. Only downside was road...
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    1 / 12
    5 of 5 bubbles (10) Excellent
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    This studio is situated in the garden of the property. Very quiet and peaceful setting. It has full bed and a jacuzzi. View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 bubbles Reviewed August 26, 2016
    We had a wonderful stay and would recommend her place to anyone. Nice, safe location and is walking distance to the subway station. Everything went extremely well thanks to Hanna.
    5 of 5 bubbles Reviewed July 18, 2016
    Great accommodations at the right price!!! Hanne was extremely helpful with how to get from the airport and to Wrigley, providing restaurant recommendations and answering any...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    West Town
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Yard
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    • Pet-friendly
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    • x
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    • x
    About this property
    A modern, recently renovated apartment located near public transit, with easy access to the prime downtown sites, and the hopping Noble Square and West Loop restaurant scenes. The building was just renovated, with lots of upgrades to make your visit comfortable and enjoyable. It features a... View all property information
    Location Information
    Chicago, Illinois 60642
    5 of 5 bubbles Reviewed 2 weeks ago
    The apartment had two true bedrooms and a nice pull out couch. The wifi was fast and reliable. No complaints!
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    1 / 15
    5 of 5 bubbles (2) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • Waterfront
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    • Pet-friendly
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    • 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
    Location Information
    Chicago, Illinois 60657
    1 / 11
    4 of 5 bubbles (5) Very good
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    • 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
    Location Information
    Chicago, Illinois 60657
    5 of 5 bubbles Reviewed October 10, 2016
    The music suite was quiet, spacious, reasonably priced, and located in a nice neighborhood. Free parking right outside, and the Paulina brown line station is a 5 minute walk away...
    5 of 5 bubbles Reviewed February 4, 2015
    Good value for the money. We enjoyed the player piano. Beds were comfortable and everything was clean.
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    1 / 14
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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    • Terrace
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    You will love my place because of the location, views/private balcony, the amazing amenities, convenience of provided essentials and host experience. With a near perfect walk score, you can get anywhere within minutes and have access to the Chicago PedWay System. My place is great for couples, solo... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 26
    5 of 5 bubbles (1) Excellent
    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Sauna
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    • Pet-friendly
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    • ?
    About this property
    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR><BR>Michigan Avenue... View all property information
    Location Information
    Chicago, Illinois 60616
    5 of 5 bubbles Reviewed December 9, 2014
    The view really is amazing and the apartment is well-equipped. After a little trouble getting in (which was solved by friendly staff right away), we found everything we...
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    1 / 40
    5 of 5 bubbles (4) Excellent
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Located in Chicago's East Lakeview Neighborhood (home of Wrigleyville and Boystown), our Junior 1-Bedroom Apartment provides peace & quiet while only minutes away from Chicago's best attractions. Steps from Lake Michigan and Belmont Harbor; with easy access to the lakefront, nightlife, dining,... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 bubbles Reviewed June 2, 2016
    My wife and I are very happy with our stay. The studio is very tastefully decorated and many amenities provided. The location was perfect for our needs. We will definitely...
    5 of 5 bubbles Reviewed April 6, 2016
    I took my three little boys to Chicago for spring break. This location was perfect. About a five minute walk from the Belmont El station and lots of bus stops nearby. Many...
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    1 / 30
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    • x
    About this property
    This beautiful unit features Eastern views of the Chicago skyline, including Willis (Sears) Tower. White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring... View all property information
    Location Information
    Chicago, Illinois 60607
    1 / 21
    5 of 5 bubbles (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Whether you are coming to stay at Raffaello Chicago for business, a romantic getaway, or traveling with your family and friends, we have the perfect accommodation ready and waiting for you.<BR><BR>Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth... View all property information
    Location Information
    Chicago, Illinois 60611
    5 of 5 bubbles Reviewed February 27, 2015
    We were lucky that we chose this place. It is in a perfectly managed hotel , Raffaello Hotel . Everything was ready to have a nice stay. Thanks
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    1 / 19
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    About this property
    Stunning Space Features wall to wall upgraded plush carpeting, beautiful open kitchen with granite countertops and stainless steel appliances, massive walk in closet with loads of storage space, floor to ceiling windows exposing eastern peak-a-boo lake views, beautifully updated bathroom, and w/d... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 10
    5 of 5 bubbles (3) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    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
    Location Information
    Chicago, Illinois 60601
    5 of 5 bubbles Reviewed March 14, 2016
    We recently stayed here for an extended weekend vacation and were very happy with this hotel. The location was perfect! Rooms were very spacious and clean! We even ordered...
    5 of 5 bubbles Reviewed June 10, 2015
    From the time that we checked in to the time that we left, everything was great. The staff and service was first rate. The rooms were clean and well kept. The front desk was very...
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    1 / 15
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    About this property
    A truly beautiful space that features a defined living area with eat in kitchen and separate bedroom space. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 7
    4.5 of 5 bubbles (9) Very good
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Yard
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    • ?
    • ?
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    • 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
    Location Information
    Chicago, Illinois 60618
    5 of 5 bubbles Reviewed 3 weeks ago
    My husband and I eally enjoyed our stay here place is cozy and perfect size. Almost everything needed was provided. Another mirror would be nice to get ready. Overall great place.
    5 of 5 bubbles Reviewed September 25, 2016
    We booked this apartment quite last minute, we wanted to find somewhere relatively cheap but still nice. Hanne's apartment fitted the bill, it was very clean and comfortable...
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    1 / 7
    5 of 5 bubbles (1) Excellent
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    It is a great location in Downtown Chicago. It is close to everywhere. Opposite side is Northwestern Memorial Hospital , following building is Ann Lurie Children's Hospital. It is walking distance to Magnificent Mile (Michigan Ave.) , Navy Pier. There are restaurants , markets all around. Welcome... View all property information
    Location Information
    Chicago, Illinois 60611
    5 of 5 bubbles Reviewed June 22, 2015
    The apartment is in a very good position. I found it clean and with all the services working perfectly.
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    1 / 21
    4 of 5 bubbles (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    One bedroom apt located in south loop Bronzeville area. Close to McCormick convention center. About 15 mins to Sox stadium.Easy access to public transportation cta bus and train. 15 mins drive to downtown. And Chinatown neighborhood.Walking distance to grocery store jewel. Walgreens .next to la... View all property information
    Location Information
    Chicago, Illinois 60653
    4 of 5 bubbles Reviewed October 31, 2016
    Emmanuel our host and his friend Tee were extremely accommodating, Emmanuel left us a fridge full of drinks and a cupboard stocked up, Emmanuel also provided lots of lovely fluffy...
    5 of 5 bubbles Reviewed September 15, 2015
    We got lost coming into the city due to road work and Emmanuel was quick to jump in his car and come to the rescue. He helped us with our bags, gave us recommendations for bars...
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    1 / 17
    5 of 5 bubbles (1) Excellent
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This unit is an officially licensed Chicago Vacation Rental. License #2438049 There’s nothing average about this 4-bedroom, 3-bath apartment in Lakeview. Whether it’s the vast interior with plenty of elbow room for 10 people, the premier location in one of Chicago’s most vibrant neighborhoods or... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 bubbles Reviewed September 17, 2016
    Really nice place, excellent location,lots of bars and restaurants. With no traffic it takes a few minutes to get to the McCormick place. I recommend it
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    1 / 28
    2.5 of 5 bubbles (2) Poor
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    High-end, furnished condo downtown Chicago will be available for vacation rental. 52nd Floor HUGE 2 Bedrooms 2 FULL Bathroom with 3 Queen Beds. Laundry In the Unit The Space The condo is fully furnished with modern design pieces - sectional leather sofas, memory foam on both beds, and feather... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 25
    Northwest Side, West Town
    Studio, 1 Bathroom, Sleeps 8 | Quick View
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    Retreat to the Windy City with this stylish studio garden suite! The property sleeps 8, boasts a location in one of the hottest neighborhoods in the city and loads of amenities making it an ideal landing spot for all of your Chicago adventures. Nestled west of Lake Michigan and south of the... View all property information
    Location Information
    Chicago, Illinois 60622
    1 / 30
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This beautiful unit features Eastern views of the Chicago skyline, including Willis (Sears) Tower. White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring... View all property information
    Location Information
    Chicago, Illinois 60607
    1 / 15
    The Loop
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Amazing unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated marble... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 27
    5 of 5 bubbles (22) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
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    Want to live like a local while staying in Chicago and save? Reserve now and take advantage of discounted rates this fall! Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our city! A family-owned, Chicago boutique vacation rental... View all property information
    Location Information
    Chicago, Illinois 60640
    5 of 5 bubbles Reviewed July 13, 2016
    My husband and I and our daughter and two grandsons from Denver all stayed at the airbandb It was a great place to stay. We had three bedrooms, two baths, a ktchen, wifi, and...
    5 of 5 bubbles Reviewed March 16, 2016
    Thank you everyone who helped make our first visit so special!!! Rental was perfect for our 4yr. olds party and mini reunion. Would do it again.Thank You Donna
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    1 / 14
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Live like a local in one of Chicago's best neighborhoods at a top-rated TripAdvisor property! Located in the vibrant and historic Andersonville, our spacious apartments are ideal for guests looking for a special getaway. Unit includes gourmet kitchen with breakfast bar, king size bed, and balcony... View all property information
    Location Information
    Chicago, Illinois 60640
    5 of 5 bubbles Reviewed May 28, 2016
    We frequently visit Chicago and find ourselves staying in the northern suburbs. This apartment rental was a find! Very classy and comfortable, room to spread out, a well stocked...
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    1 / 11
    The Loop
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    A kitchenette is provided in every spacious suite at Grand Riverfront at Chicago. Extras include a sofa bed and flat-screen cable TV. Private bathrooms also come with a bath or shower. A fitness centre is available at Grand Riverfront at Chicago. Other facilities like meeting facilities, luggage... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 24
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Suite Details * King bed in Master Bedroom and Queen Size Sofa bed in living room * Living room and separate kitchen * Floor to ceiling windows with city view * Fresh Cotton Linens and Towels Provided * Bamboo Wood Floors * Fully Equipment Kitchen with all Major Appliances including Fridge, Stove,... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 14
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 359724 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Experience luxury in Chicago by staying in this wonderful one bedroom condominium that... View all property information
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    Chicago, Illinois 60611
    1 / 40
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Take in views of the entire city from this massive Iconic skyscraper in downtown Chicago. Experience elite luxury and comfort from your own perch overlooking the Chicago skyline. This building is equipped with full gym, indoor outdoor pools and hot tubs, dry and wet saunas, and on-site 5-star... View all property information
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    Chicago, Illinois 60601
    1 / 51
    3 of 5 bubbles (2) Average
    Near North Side
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Included is a 3-bedroom fully furnished “Old Town Chicago” condo with TWO PRIVATE BALCONIES, Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service upon Vacating Included, Complimentary Laundry, and all of the atmosphere... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 26
    5 of 5 bubbles (1) Excellent
    Lakeview
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
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    • x
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    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! Beautifully furnished and fully equipped--guaranteed a unique and unforgettable experience for you, your family and friends. Rest... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 bubbles Reviewed December 23, 2015
    Stayed in this house for three nights and had family come in for Christmas get together. It was absolutely perfect. The home is very well maintained with all of the personal...
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    3 bedrooms, 2 full bathrooms, Balcony with Grill, sleeps 8. Kid Friendly Live like a local in one of Chicago's best neighborhoods at a top-rated TripAdvisor property! Located in a family-owned boutique building in the vibrant and historic Andersonville neighborhood, our Chicago vacation property... View all property information
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    Chicago, Illinois 60640
    1 / 16
    5 of 5 bubbles (1) Excellent
    Lincoln Park
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Vacation in your own charming historic Lakeview / Lincoln Park 2-bdr & 2.5-bth Coach House with deck. Enjoy modern furnishings and amenities comfortably accommodating up to six guests. When you’re ready to explore the area, grab a bite to eat, drink, shop or play -- just a few steps out your door... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 21
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
    • ?
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    About this property
    Beautiful open floorplan studio with wall to wall bamboo hardwood flooring, open kitchen with tile backsplash, stainless steel appliances, and granite countertops, huge walk-in closet, floor to ceiling windows exposing city views, updated large bathroom with stone surround, and w/d in unit. Great... View all property information
    Location Information
    Chicago, Illinois 60654
    1 / 25
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Whether you are coming to stay at Raffaello Chicago for business, a romantic getaway, or traveling with your family and friends, we have the perfect accommodation ready and waiting for you.<BR><BR>Every Raffaello guest room reflects an upscale European style with soothing accents, subtle earth... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 12
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Our suite features Two Bedrooms/Two Bathrooms with a pull out couch and can accommodate six guests. Suite also contains fully equipped gourmet kitchen and is perfect for families or individuals, traveling for business or pleasure. Guests can enjoy their individual balconies with gas grill as well... View all property information
    Location Information
    Chicago, Illinois 60640
    5 of 5 bubbles Reviewed August 26, 2015
    This apartment is specious, clean and luxurious. the living seating area has a comfortable couches and big TV. The kitchen is elegant and fully equipped. The staff are really...
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    1 / 21
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 359720 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Experience luxury in Chicago by staying in this wonderful one bedroom condominium that... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 10
    The Loop
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Ref # 360127 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Have your very own private space while in Chicago by staying in this remarkably... View all property information
    Location Information
    Chicago, Illinois 60661
    1 / 12
    5 of 5 bubbles (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Waterfront
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    • x
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    • x
    About this property
    Elegant 1 bedroom apartment on N Lake Shore Drive,10 min away from Michigan Avenue, Northwestern Memorial Hospital, 25 min by bus to Millenium Park and the Art Institute. Fully furnished, 900 sq ft,beautiful oak floors, high ceilings, custom architectural details.Perfect residential accommodations... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 bubbles Reviewed April 15, 2012
    We were in Chicago to visit our daughter and this was our first stay at this 1 bedroom apartment. It was absolutely wonderful - cozy, well-appointed and suited our needs...
    5 of 5 bubbles Reviewed December 8, 2011
    My friend and I were blown away by this apartment, beautifully accomodation and accessible to the city with 3 regular buses passing by. The owner was very helpful and...
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    1 / 11
    Lakeview
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Our updated Lakeview/Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 10 Premier location near shopping, dining and parks Gourmet-inspired kitchen with full appliance package Recently furnished with modern appointments Classic meets contemporary interior WiFi and cable Linens... View all property information
    Location Information
    Chicago, Illinois 60657
    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.