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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 / 6
    5 of 5 bubbles (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    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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    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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    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 / 21
    5 of 5 bubbles (3) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Situated feet from Logan Square itself and the (underground and quiet) Logan Square Blue Line train stop for easy 24/7 downtown & O'Hare access. We also provide free permits for convenient street parking on our block. We've lovingly preserved our 1907 home and look forward to hosting you in... View all property information
    Location Information
    Chicago, Illinois 60647
    5 of 5 bubbles Reviewed 2 weeks ago
    We came to Chicago to spend some time with our adult daughter for an extended weekend. She was traveling back from Canada to her home in Australia. This home was easy for her to...
    5 of 5 bubbles Reviewed July 5, 2016
    Alex is a phenomenal host. We had everything we needed and then some. This home is conveniently located by the L and Logan Square. This 1907 Greystone is perfectly decorated and...
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    1 / 29
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
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    About this property
    Andersonville, Edgewater, Loyola's campus and great restaurants, like Uncommon Ground, are a block away. Shopping and the lakefront are less than a 5 min walk away. There's no need for a car here, it's a short walk to the red line. The Space This is a large, bright, happy space. The apartment is... View all property information
    Location Information
    Chicago, Illinois 60660
    5 of 5 bubbles Reviewed October 5, 2016
    I don't think you'd get better anywhere - a superb combination of classy accommodation, quiet location and faultless host - thanks so much John. Use Uber to get around at very...
    5 of 5 bubbles Reviewed September 21, 2016
    Was very please with reservation, excellent communication with owner. Very accommodating. Clean nice decor, Nice well equip kitchen. Quiet residential neighborhood
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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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    About this property
    NO LARGE PARTIES!!!!great riverwest location in the heart of the city(1346 west augusta). 3 bed, 2 bath. 2800 square feet. 17 foot ceilings. perfect for entertaining. pool table, 115" movie theater,dart board, 2 blocks to bus/train line. you wont be disappointed. two bedrooms are located in the... View all property information
    Location Information
    Chicago, Illinois 60642
    5 of 5 bubbles Reviewed June 7, 2016
    The photos of this property do not quite do it justice. This property was everything and more than we had hoped for. This property is way bigger than it appears in the photos...
    5 of 5 bubbles Reviewed March 22, 2016
    Everything went excellent! Easy to get to resturants and bars. My friends and i were very impressed with the spacious home. It was clean and ready for entertaining. Pool table and...
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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 / 56
    5 of 5 bubbles (42) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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 / 11
    4 of 5 bubbles (5) Very good
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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 / 12
    5 of 5 bubbles (10) Excellent
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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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 / 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 / 28
    2.5 of 5 bubbles (2) Poor
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 / 32
    5 of 5 bubbles (4) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • Hot Tub
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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 / 11
    4.5 of 5 bubbles (2) Very good
    Northwest Side
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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 / 12
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 14
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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 / 26
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Ref # 376168 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. *This unit is being Furnished On-Demand by HomeSuite! Photos are meant to give you a... View all property information
    Location Information
    Chicago, Illinois 60611
    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
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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 / 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 / 25
    Northwest Side, West Town
    Studio, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    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
    5 of 5 bubbles (40) Excellent
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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
    Location Information
    Chicago, Illinois 60625
    5 of 5 bubbles Reviewed September 27, 2016
    This spacious basement floor was very comfortable and attractive with room to relax and catch up with washing. The owner was very thoughtful providing tourist information, snacks...
    5 of 5 bubbles Reviewed September 6, 2016
    Chicago..a place that we had yet to visit and was on the summer vacation bucket list. In looking for lodging, our criteria was comfort, access to public transportation and...
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    1 / 12
    5 of 5 bubbles (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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 / 9
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Ref # 360239 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. For a spectacular Chicago experience, stay in this fully furnished 1 bedroom, 1... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 15
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
    Location Information
    Chicago, Illinois 60618
    1 / 10
    5 of 5 bubbles (3) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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 / 38
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    Ref # 360350 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. Glide your way to this fully furnished 1 bedroom, 1 bathroom loft in Chicago. Modern... View all property information
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    Chicago, Illinois 60610
    1 / 13
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 359555 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. Come home to this gorgeous and furnished one bedroom condo in Chicago. It has a fully... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 17
    5 of 5 bubbles (1) Excellent
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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 / 10
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Live like a local and save! Book now to take advantage of discounted fall rates! Beautiful 2 Bedroom unit in boutique luxury building with 24 hour concierge service. Located in the wonderful and historic Andersonville neighborhood, The Guesthouse Chicago vacation rental encourages you to live... View all property information
    Location Information
    Chicago, Illinois 60640
    5 of 5 bubbles Reviewed May 18, 2015
    Great property in Chicago, a short distance from Lakeshore Drive, perfect for a family vacation. We stayed in the spacious 2 bed/2 bath unit. The unit was stunning, with beautiful...
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    1 / 59
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    2nd Floor apartment with 3 bedrooms, 1 bath, full living room, full dining room, full kitchen. So close to Wrigley field you can sit in your living room and listen to concerts like, Billy Joel, Nirvana, Paul McCartney etc. Walk 1/2 block to the new plaza and shops when construction is complete.... View all property information
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    Chicago, Illinois 60613
    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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    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 / 25
    Lakeview
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Lakeview neighborhood is an incredible Chicago experience! We live 3 blocks from the Brown Line stop, just a 7 minute walk from Wrigley field, right next door to some amazing Southport Corridor shopping, and terrifically close to a lot of other amazing venues. This apartment is completely... View all property information
    Location Information
    Chicago, Illinois 60657
    1 / 6
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Perfect location for a Chicago getaway or for a work trip!!! This Great home with a Great location is steps away from all Chicago has to offer with loads of restaurants, shops and sightseeing. Just a mile from the zoo, a few more to the lakefront for biking, running, rollerblading, walking and... View all property information
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    Chicago, Illinois 60610
    1 / 15
    5 of 5 bubbles (2) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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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    Chicago, Illinois 60657
    1 / 19
    4 of 5 bubbles (1) Very good
    Lakeview
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    HOT WINTER MONTHLY RATES Starting at $99Nt (30 Night Min) January / February / March ONLY NO TAX on Monthly Rentals Cleaning Fee NOT Included 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... View all property information
    Location Information
    Chicago, Illinois 60613
    4 of 5 bubbles Reviewed August 9, 2015
    Our extended family of six had a great time in Chicago, thanks in large part to having Teri's Guesthouse as the base for the busy weekend of wedding events. We even had a...
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    1 / 7
    3.5 of 5 bubbles (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Last min cancellation trying get my renter some of her deposit back for her!In the heart of Pilsen in Chicago's Artist community. Beautiful city views. Unique space in Chicago's Historic district. One block from Thalia Hall. Fire Place, Brand new Bathroom/custom tile. Restored original Red hardwood... View all property information
    Location Information
    Chicago, Illinois 60608
    4 of 5 bubbles Reviewed July 19, 2016
    As long as you manage your expectations, this place is great! W It's in a rowhouse they are renovating in a Pilsen, a mostly hispanic area of town.The neighborhood is up and...
    3 of 5 bubbles Reviewed June 1, 2016
    The loft is decorated in a fun Moroccan theme. The building is nice and we found free street parking less than a block away. Walking distance to restaurants, bars and public...
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    1 / 39
    4.5 of 5 bubbles (19) Very good
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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. We are city bee keepers as we learned they are very important for our... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 bubbles Reviewed September 27, 2016
    A comfortable and cozy living quarters. Not downtown but close to CTA bus/subway lines so easy to get around. Costco about a mile away! Hanne is a great host, very helpful and...
    4 of 5 bubbles Reviewed July 13, 2016
    We loved staying here for our quick anniversary getaway! It was a short walk to the bus and train. We definitely would stay here again!
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    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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. The Guesthouse Hotel offers great style, comfort and value. Stay... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 9
    3 of 5 bubbles (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Chicago, Illinois 60618
    3 of 5 bubbles Reviewed August 9, 2016
    Comfortable, large and roomy apartment with good air com and wifi, in a residential area. The apartment is approx 30- 45 mins from the centre of Chicago with very good public...
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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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    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 / 11
    The Loop
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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 / 21
    5 of 5 bubbles (1) Excellent
    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
    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 / 27
    5 of 5 bubbles (22) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 / 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 / 23
    5 of 5 bubbles (1) Excellent
    Lincoln Park
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Historic cottage in exclusive Lincoln Park neighborhood. 3 bedrooms (1 King and 2 Queens); 2 full and 1 half bath; laundry; full kitchen and family room; media room; 2 car garage; living and dining room; outdoor decks; walking distance to DePaul University, Lincoln Avenue entertainment district,... View all property information
    Location Information
    Chicago, Illinois 60604
    5 of 5 bubbles Reviewed September 2, 2015
    My friends and I spent the weekend at Paul's house for our fantasy football draft. The house is in walking distance to Wrigley field and lake shore drive. It easily accommodates 6...
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    1 / 11
    Lakeview
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 48
    5 of 5 bubbles (17) Excellent
    Southwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Details: __ Large Comfortable Apartment That You Will Love __ 5 Star Reviews. __ 2nd Apartment Available. You Can Rent the Entire Building. Our Location: __ 15 Minutes to Everything that is Chicago. __ One Click and Uber or Lyft transport you. __ 15 to Navy Pier, Millennium Park,... View all property information
    Location Information
    Chicago, Illinois 60609
    5 of 5 bubbles Reviewed July 5, 2016
    I traveled with colleagues to Chicago for a conference in June. This was our second time staying in this particular apartment. Bob's place is very clean and well maintained. The...
    4 of 5 bubbles Reviewed January 4, 2016
    Even in the nicest hotels, it can be hard to be away from home -- you lose your privacy and all that you enjoy about your personal routine. Waking up in the middle of the night...
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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.