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Apartment Rentals and Condos in Chicago, IL

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    Travelers to Chicago are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 21
    5 of 5 stars (3) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 7
    4 of 5 stars (9) Very good
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 10
    5 of 5 stars (3) Excellent
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 16
    5 of 5 stars (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 / 11
    4.5 of 5 stars (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 stars Reviewed 4 weeks ago
    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 stars 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 / 40
    5 of 5 stars (4) Excellent
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 stars 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 stars 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 / 10
    5 of 5 stars (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 stars 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 stars 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 / 11
    4 of 5 stars (4) 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 stars Reviewed February 4, 2015
    Good value for the money. We enjoyed the player piano. Beds were comfortable and everything was clean.
    4 of 5 stars Reviewed July 28, 2014
    Close to transit & grocery. Lots of space. Communication with Andy was great. He answered any questions we had before the trip in a timely manner. Easy check in and out...
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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 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
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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
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    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 / 8
    3.5 of 5 stars (3) Average
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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
    Location Information
    Chicago, Illinois 60630
    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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    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
    • Private Yard
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    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 stars Reviewed 2 weeks ago
    I really enjoyed the condo with it stylish decor. John was so nice and accommodating. I needed a early check in and late check out and John accommodated both request. There was...
    5 of 5 stars Reviewed June 18, 2016
    This is a fabulous flat, exceptionally clean, comfortable, well equipped and well decorated! John is an extremely thoughtful host, providing fresh flowers in every room, fresh...
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    1 / 22
    Lincoln Square
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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
    Location Information
    Chicago, Illinois 60625
    1 / 12
    5 of 5 stars (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 stars 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
    5 of 5 stars (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 stars 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 / 15
    5 of 5 stars (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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    • 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 / 21
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Outdoor Dining Area
    • Porch
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    • Pet-friendly
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    • x
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    • x
    About this property
    The space is fresh and open and can sleep 8 on individual beds and 12 if you double up on the queen mattresses. There are 2 sets of bunk beds in a small 3rd bedroom/bonus room. There are 2 living rooms which makes it easy to get away from your mates when one wants to have some quiet time or giving... View all property information
    Location Information
    Chicago, Illinois 60622
    1 / 56
    4.5 of 5 stars (35) Very good
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    • Pet-friendly
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    • ?
    • ?
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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 stars Reviewed July 17, 2016
    I did a LOT of research before deciding to stay here. I firmly believe you will not find a better value in the Chicago area. The vacation rental is just outside of the hustle...
    4 of 5 stars Reviewed July 7, 2016
    Hanne has a lovely place and was a very pleasant person. I was visiting the States from the UK with my elderly parents. The steps at the front of the house was hard work for them...
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    1 / 16
    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<BR><BR>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... View all property information
    Location Information
    Chicago, Illinois 60640
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    TWO-BEDROOM SUITES WITH BALCONY Open gourmet kitchen with stainless appliances Granite breakfast bar Bright and sunny living room with 10' ceilings Private balcony complete with gas grill and patio furniture King-sized bed in the master bedroom Spa-like bathroom with glass shower Two Bedroom... View all property information
    Location Information
    Chicago, Illinois 60640
    1 / 18
    4 of 5 stars (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 9 | Quick View
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    • x
    About this property
    Welcome! Welcome!Our single family brick house is located in a rare semi-private block about 5 miles West of Downtown Chicago. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen, Washer/Dryer. If you enjoy a quiet home with free parking, newer beds, clean sheets and towels,... View all property information
    Location Information
    Chicago, Illinois 60644
    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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    1 / 8
    4 of 5 stars (3) 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
    5 of 5 stars 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!
    3 of 5 stars Reviewed July 11, 2016
    Owner seems new to visitor needs. Unit is really too small for 5 or 6 guests. Items that need to be addressed: 1). Let guests know they can request fresh bath towels. We had...
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    1 / 6
    3.5 of 5 stars (3) Average
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Charming, roomy one bedroom , with open kitchen and living space. This recently refurbished loft-style apartment gives visitors to Chicago a chance to visit and explore whist enjoying the comforts of modern living. Hardwood floor, and ceramic tiles in kitchen and bathroom. Plenty of sitting... View all property information
    Location Information
    Chicago, Illinois 60618
    4 of 5 stars Reviewed September 16, 2014
    The accommodations were not real fancy but well suited for a busy stay in Chicago! Excellent location for the price. Wrigley and other top sites are easily accessible. If you are...
    3 of 5 stars Reviewed June 15, 2014
    Ok so if you're expecting a pretty little getaway in Chicago with views and a location then this place isn't for you. The apartment is located atop of a commercial building that's...
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    1 / 23
    5 of 5 stars (1) Excellent
    Lincoln Park
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    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 stars 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 / 9
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    • x
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    • x
    About this property
    Large, roomy two bedroom loft like apartment tastefully appointed and furnished. Hardwood floors and ceramic tiles in kitchen and bathroom. Plenty of sitting room with large screen TV, fireplace and free WiFi. Two full bedrooms, one with a king sized and the other with a queen sized bed. You... View all property information
    Location Information
    Chicago, Illinois 60618
    3 of 5 stars Reviewed 2 weeks ago
    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 / 97
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Our 3 bedroom cozy house feels like a cottage in the middle of the popular Avondale Neighborhood. It's perfect place for a family up to 8, we are a block from a park, Target and the river. Enjoy restaurants and a craft brewery all within in 3 blocks.<BR><BR>Entire house with 2 bedrooms and bath... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed October 3, 2015
    This 4 bedroom 2 full bath was very clean, well stocked, in a good neighborhood, had a very nice park for our grand children to play at within a block, great restaurants within...
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    1 / 21
    5 of 5 stars (1) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    An irresistibly charming apartment! Good things do come in small packages! Walk in to the home and the first thing you notice is nothing, absolutely nothing, has been overlooked. You’ll be engulfed in warm inviting hues. The beauty & integrity of the historic Greystone recaptured; undeniably... View all property information
    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed June 15, 2015
    We were very happy finding this vacation rental. The location was accommodating to our interest. The apartment was excellent. We were able to stay altogether and enjoy the...
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    1 / 25
    The Loop
    2 Bedrooms, 6 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Fabulous 2 bedroom apartment. 3 queen beds, sofa, 2 bathrooms. Great views and amazing amenities. Very close to Michigan & State. Within walking distance to the Lake and Millennium Park. All subway lines just few steps away. Apt has wifi, cable. Clean and modern high rise, two bedroom apartment,... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 14
    5 of 5 stars (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 stars 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 / 7
    3.5 of 5 stars (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    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 stars 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 stars 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 stars (18) Very good
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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
    4 of 5 stars 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!
    4 of 5 stars Reviewed July 13, 2016
    Our stay at this rental was mostly pleasant. It's situated in the northern suburbs of Chicago. There were plenty of restaurants and stores in the neighborhood. Parking can be...
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    1 / 11
    5 of 5 stars (1) Excellent
    Lincoln Square
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Our basement studio is perfect for people who want to explore downtown yet get a feel for a true Chicago neighborhood. It feels more like your own apartment than a hotel room. There is no need for a car as we are close to the Brown Line stop. Our rental space has its own entrance and is separate... View all property information
    Location Information
    Chicago, Illinois 60625
    5 of 5 stars Reviewed 1 week ago
    This property looks nice in the photos, but it was even better than we expected. The actual apartment is clean, spacious, and inviting. The bathroom and bedroom areas are large...
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    1 / 7
    5 of 5 stars (4) Excellent
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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 stars Reviewed July 14, 2016
    We were in town to visit. This gave us a quiet spot between visits and adventures. Host responds quickly to any needs.
    5 of 5 stars Reviewed June 16, 2016
    It was a pleasure to stay here. We were to check in on Memorial Day and we were late to our 4 p.m. check in time. I texted Hanne and she said that it would not be a problem and...
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    1 / 27
    4.5 of 5 stars (6) Very good
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 60605
    4 of 5 stars 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 stars 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 / 21
    5 of 5 stars (2) Excellent
    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
    5 of 5 stars 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...
    5 of 5 stars Reviewed August 15, 2015
    The host, Emmanuel, was exceptionally friendly and helpful. He was very kind and helped us to the apartment with our bags. We had arrived an hour prior to what we had said as we...
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    1 / 17
    Lakeview
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
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    Chicago, Illinois 60613
    1 / 12
    5 of 5 stars (9) Excellent
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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 stars Reviewed 3 days ago
    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 stars 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 / 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
    Location Information
    Chicago, Illinois 60613
    1 / 6
    2.5 of 5 stars (4) Poor
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    2 bedroom 2 bathroom Apartment Sleeps 4 2 queen beds 5 min walk to Blue Line Station in Logan Square 25 min to Downtown... View all property information
    Location Information
    Chicago, Illinois 60647
    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...
    4 of 5 stars Reviewed September 29, 2013
    We stayed in apartment #3 which is different from the one in the photos on TripAdvisor. (sorry, I didn't take any photos to include) Booking this apartment was a bit difficult...
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    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    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 stars 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 / 50
    5 of 5 stars (1) Excellent
    Lincoln Park
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Fully furnished luxury apartment in the heart of Lincoln Park next to Oz Park. Walkscore 97/100. Brand new recently fully renovated 1 bedroom apartment, bathroom with jacuzzi tub, fireplace, hardwood floors, in unit laundry, private entrance and kitchen with new appliances. 700 square... View all property information
    Location Information
    Chicago, Illinois 60614
    5 of 5 stars Reviewed July 8, 2016
    I previously lived in Chicago for 5 years and chose this place based on the neighborhood. Not only is the Armitage and Halsted area the nicest part of Lincoln Park (with an 18...
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    1 / 15
    4 Bedrooms, 1 Bathroom, Sleeps 17 | Quick View
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    About this property
    Room type: Entire home/apt Property type: Apartment Accomodate: 12+ Bedrooms: 3 Bathrooms: 1 Beds: 5 Check In: 3:00 PM Check Out: 12:00 PM Amenities Wifi Parking Kitchen utensils Price Extra People: $18 / night after the first guest . Cancellation level? Cleaning Fee: None Security Deposit:... View all property information
    Location Information
    Chicago, Illinois 60608
    1 / 22
    5 of 5 stars (1) Excellent
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    The Duplex Condo is located in the vibrant Gold Coast neighborhood, one of Chicago's most affluent and treasured residential areas with quiet, tree-lined streets, stately homes and connections to the city's past. This property is in a Charming historic lowrise brick building. It has a bright and... View all property information
    Location Information
    Chicago, Illinois 60610
    5 of 5 stars Reviewed September 30, 2015
    The place was neat, confortable and very well located. We enjoyed our time, and would definitely stay there again. Vee was truly thoughtful. Absolutely recommendable
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    1 / 23
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our place is close to everything you could hope for when visiting Chicago! Walking distance to: Soldier Field, Grant Park, Buckingham Fountain, Field Museum, Shedd Aquarium, amazing grocery stores and restaurants, the CTA, Divvy bikes, and Michigan Ave. As well as a little over 1 mile to: The Art... View all property information
    Location Information
    Chicago, Illinois 60605
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    This historic turn of the century home has been recently remodeled while paying homage to original and period details like crown moldings and stained glass. Fresh, clean and sparkling with drop dead mid century décor. Both comfortable, roomy and stylish. There is a large fully stocked kitchen with... View all property information
    Location Information
    Chicago, Illinois 60625
    1 / 11
    The Loop
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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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 / 22
    West Town
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Balcony
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    • x
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    About this property
    Here you'll find a wonderful, recently renovated two bedroom apartment with lots of upgrades to make your visit comfortable and enjoyable. There's a spacious backyard, high ceilings, new appliances and all the essential (plus some extras) so you'll feel right at home! The building is conveniently... View all property information
    Location Information
    Chicago, Illinois 60642
    1 / 6
    Near South Side
    2 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
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    A nice place to stay in the heart of Chicago. Beautiful home in a very convenient location. Lots of transportation, food, and entertainment, right at your fingertips. The home is also located within walking distance of McCormick Place, so if you're coming in town for a convention, this is place for... View all property information
    Location Information
    Chicago, Illinois 60616
    1 / 41
    5 of 5 stars (23) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Spacious Bright Loft in the Heart of Everything Chicago 2 -10 adults, up to 12 with children Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Park home can be your home away from home in Chicago. If you’re heading to Chicago and looking to be near downtown but... View all property information
    Location Information
    Chicago, Illinois 60642
    5 of 5 stars Reviewed 2 weeks ago
    Wow, it's going to be hard to limit this as start to finish I can't say enough good things. I had never booked this type of vacation rental before and was very nervous that...
    5 of 5 stars Reviewed June 25, 2016
    Our family of five loved our stay at the Magic Factory. The loft is beautifully decorated with great amenities and a comfortable living room for reading or watching movies. If you...
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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.