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Lofts and Condos in Chicago, IL

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    All 181 Rentals in Chicago
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    Travelers to Chicago are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 13
    5 of 5 stars (2) Excellent
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    1 / 12
    5 of 5 stars (1) Excellent
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
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    1 / 11
    5 of 5 stars (1) Excellent
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    1 / 48
    5 of 5 stars (14) Excellent
    Southwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
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    About this property
    We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow... View all property information
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    Location Information
    Chicago, Illinois 60609
    5 of 5 stars Reviewed April 3, 2015
    The location is in a quaint neighborhood. We enjoyed the location because you felt like part of the area. The apartment was very spacious. It was truly a home away from home...
    5 of 5 stars Reviewed April 7, 2014
    Our family of four (two teens) spent 5 days here during spring break and had an excellent experience. We went downtown every day by catching the red line train at the 35th/Sox...
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    1 / 15
    4.5 of 5 stars (3) Very good
    Studio / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
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    • Elder access
    • x
    About this property
    Furnished Studio. Double bed, full bath, and full kitchen. Unique location. You don't need a car living here. Plenty of transit options. A couple of blocks to Red line train station. Direct express bus to Chicago downtown stops right around the corner. 20 minutes to the city center by public... View all property information
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    Location Information
    Chicago, Illinois 60640
    4 of 5 stars Reviewed September 3, 2014
    Great stay, close to the El train and cheaper than a hotel! Able to stay parked out front for free and take the El where ever we wanted to. If you want a great stuffed pizza...
    5 of 5 stars Reviewed July 8, 2014
    the location of the apartment we stayed was convenient enough:only some min away from the red line train and a min from the bus stop,so getting to downtown is easy.we got a great...
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    1 / 23
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Balcony
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    • Internet Access
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    The South Loop is classic Chicago. In the South Loop, streets with decades of history come alive as music and life pulse magnetically. Chicago's South Loop is a neighborhood that's buzzing with bars, restaurants and entertainment; it's the perfect place to stay during your time in Chicago. The... View all property information
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    Chicago, Illinois 60616
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    1 / 40
    4.5 of 5 stars (6) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
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    • Gym
    • Housekeeping...
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    • Pool Table
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    888.761.RENT or 312.242.1625 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) Check Availability and Book Online Now: http://reservation.worldweb.com/hotel/1278... View all property information
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    Location Information
    Chicago, Illinois 60661
    5 of 5 stars Reviewed July 19, 2014
    Beautiful furnished apartments with kitchennete and in the heart of downtown, just a few blocks away from State st and michigan ave. I had a very pleasant and comfortable stay...
    5 of 5 stars Reviewed May 7, 2014
    The location is so convenient, the blue line train from O'hare airport takes you right to the stop of which is about 5 minutes walk to the building. The unit is clean and with...
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    1 / 14
    5 of 5 stars (12) Excellent
    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    This is a nice place on a quiet street, close to transportation and many restaurants. Very close to I 94. View all property information
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    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed May 11, 2015
    Our stay was really quite comfortable with very nice surroundings. Many bedding plants and flowers in plant boxes on the porch as well as the yard. Nicely furnished at a...
    5 of 5 stars Reviewed May 5, 2015
    Great & confortable house, nice neighborhood and extraordinary city. You don't need to rent a car to enjoy the city. Hanne is pretty kindly and her recommendations are usefull...
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    1 / 43
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • ?
    • x
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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
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    Location Information
    Chicago, Illinois 60657
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    1 / 11
    5 of 5 stars (2) Excellent
    DePaul
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    BEFORE YOU BOOK PLEASE NOTE THERE IS A 4 NIGHT MINIMUM FROM MAY THROUGH OCTOBER, WITH A 5 NIGHT MINIMUM FOR HOLIDAY WEEKENDS AND SPECIAL EVENT WEEKENDS. PLEASE DO NOT AUTO BOOK FOR PERIODS SHORTER THAN WHAT IS REQUIRED AS THE BOOKING MAY NOT BE HONORED. PLEASE EMAIL OR CALL WITH ANY QUESTIONS.... View all property information
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    Location Information
    Chicago, Illinois 60614
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    1 / 14
    5 of 5 stars (2) Excellent
    DePaul
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
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    About this property
    This Unit has one regular sized bedroom and a 'Lil' bedroom - twin bed only. Located 1 block from the Fulllerton L stop (Brown Purple & Red Line service), getting around the Windy City is a breeze. Magnificent Mile in under 10 minutes, the Loop (Grant Park, Millennium Park, Museum Row) in 12. With... View all property information
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    Location Information
    Chicago, Illinois 60614
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    1 / 20
    4.5 of 5 stars (4) Very good
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Plenty of free street parking is available on our block. This is the first floor of our home so we expect all guests to be QUIET & respectful. If you love to party, stomp around and yell then this is not the place for you. No parties, no loud music & no stumbling in drunk at 2 am. We are old &... View all property information
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    Location Information
    Chicago, Illinois 60609
    4 of 5 stars Reviewed September 3, 2014
    This was my first experience using Trip Advisor and renting a private home to stay in. The weekend was great. The apartment was located in a safe neighborhood to walk around in...
    5 of 5 stars Reviewed November 11, 2013
    From start to finish this rental was perfect. I was hesitant to rent from a private party, however great communication early on helped put me at ease. As a solo traveling female I...
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    1 / 49
    5 of 5 stars (30) Excellent
    Southwest Side
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    We have two really incredible vacation rental apartments. The view in our first picture is our large hot tub. It's your new best friend after a day of travel, sightseeing, or business. The next photo is the amazing Chicago City Skyline view from our deck (closed in winter when there is snow... View all property information
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    Location Information
    Chicago, Illinois 60609
    5 of 5 stars Reviewed November 13, 2014
    Our family of four had an excellent time at this apartment. Bob was very easy to deal with and extremely helpful. Key code access to the apartment was very convenient. A garage...
    4 of 5 stars Reviewed September 27, 2014
    We were very pleased with our stay at this facility. It isn't in the typical touristy area which we liked as it made our urban experience feel more authentic and any neighbors we...
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    1 / 18
    4 of 5 stars (1) Very good
    The Loop
    Studio / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    Location Information
    Chicago, Illinois 60602
    4 of 5 stars Reviewed August 20, 2014
    Tr`es bien situé, propre et bien équipé. Personnel de l'immeuble bien chaleureux. Pitsfield's café `a ne pas manqué au rez-de-chaussée. Calme , bien insonorisé...`a l'exeption de...
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    $300
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    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Gorgeous 2 bedroom/1 bath located on the second floor of a classic Chicago 3-flat. Building is located in the heart of Lakeview, steps to the cta (no train noise), and walking distance to Wrigley Field and the Lake. Building had a full renovation in 2014 including a brand new kitchen with gorgeous... View all property information
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    Location Information
    Chicago, Illinois 60657
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    $95
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    1 / 10
    5 of 5 stars (1) Excellent
    Lakeview
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is a beautiful garden unit. It comes fully furnished with a queen size bed plus a pull-out couch. Plenty of sitting room, updated bathroom, does not have kitchen but does have small fridge, microwave and coffee maker. The location is ideal, being close to the city and still in a quiet... View all property information
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    Location Information
    Chicago, Illinois 60657
    5 of 5 stars Reviewed October 13, 2014
    My wife and I spent 3 night here in Sept 2014. The owner was very friendly and helpful. This studio is located in a nice quiet neighborhood, close to restaurants and shops, and...
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    $259
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    1 / 37
    4 of 5 stars (5) Very good
    Near North Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Studio Apartment Downtown Chicago Millennium Park walking distance most attractions close to public transportation... View all property information
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    Location Information
    Chicago, Illinois 60611
    4 of 5 stars Reviewed August 18, 2014
    Very strategic location near to major attractions. Very spacious and quiet. The best coffee is just down the building! The only thing was the wifi was extremely slow, me and my...
    3 of 5 stars Reviewed July 1, 2014
    security was not aware of our check in and had to call and verify. kitchen is not adequately stocked for those who may use knives, forks and wine glasses. it was, however...
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    1 / 8
    4.5 of 5 stars (2) Very good
    Northwest Side
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travelers have booked this property
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    • Air Conditioning
    • Balcony
    • Dryer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This very affordable two bedroom, two bathroom apartment can sleep up to six guests. There are queen sized beds in each bedroom and a pull out couch in the living room. With features including: a breakfast table in the well-appointed kitchen; dining room; comfortable living room; a balcony;... View all property information
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    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 / 7
    5 of 5 stars (1) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    If you are looking for a private, cozy, and comfortable place then this is just right for you. Here you can relax and lay back in a newly renovated unit with a private entrance for your convenience. Let the travel stress behind you and enjoy your stay in that great City we call HOME, Chicago We... View all property information
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    Chicago, Illinois 60618
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    $247
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Grill
    • Gym
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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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
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    Location Information
    Chicago, Illinois 60640
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    $85
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    1 / 16
    5 of 5 stars (33) Excellent
    Northwest Side
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    A big thank you to my guests for their great reviews. I'm so honored to have earned a 2014 Certificate of Excellence from tripadvisor! Very comfortable, private lower level of duplex. Perfect for a business traveler who doesn't want to be downtown, or a couple visiting the city for pleasure.... View all property information
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    Location Information
    Chicago, Illinois 60625
    5 of 5 stars Reviewed May 21, 2015
    Cheryl made us feel like a guest in her home. She has a gift of hospitality that made our stay there welcoming and enjoyable. There is plenty of room and very clean and...
    4 of 5 stars Reviewed December 10, 2014
    Cheryl's apartment worked perfectly as a home base for my husband and me during a long weekend's visit to Chicago. We spent much of our time in and around the Loop, but found the...
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    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
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    Chicago, Illinois 60640
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    $195
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    1 / 10
    5 of 5 stars (1) Excellent
    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • 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
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    Location Information
    Chicago, Illinois 60601
    5 of 5 stars Reviewed December 2, 2014
    For downtown Chicago stay, this was fantastic...lots of room and great location! We were a walk away from anything...from Navy Pier to the beach to shopping to family museums. A...
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    1 / 7
    Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • 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
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    Location Information
    Chicago, Illinois 60611
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    $999
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    1 / 55
    Northwest Side, Wicker Park / Bucktown
    3 Bedrooms / 5 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
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    About this property
    Architecturally significant single family home in Chicago's best neighborhood, Wicker Park. This home has been featured in design magazines and is ideal for entertaining. Filled with mid-mod furnishings throughout. Forbes rated Wicker Park #4 in the country for hippest neighborhoods, and this home... View all property information
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    Location Information
    Chicago, Illinois 60622
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    $199
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    1 / 16
    Roscoe Village
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Village is a very family friendly neighborhood. This warm and welcoming first floor unit features a high end kitchen equipped with stainless appliances & granite countertops, 1 King... View all property information
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    Location Information
    Chicago, Illinois 60618
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    $395
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    1 / 34
    Lincoln Square
    5 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Balcony
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    • Hot Tub
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    About this property
    Huge 5 Bedroom-4.5 Bathroom home, 4 fire places, completely remodeled, fully furnished. Equipped kitchen with large breakfast island, separate dining room seating 8-10. Family room off the kitchen with fire place, huge deck and private back yard. Huge master bedroom with decorative fire place,... View all property information
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    Chicago, Illinois 60625
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    Northwest Side
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    Enjoy the entire house for a fraction of any hotel. Our house is a 10 room, 4 Bedroom, 3.5 Bathroom. Completely remodeled with huge fully equipped kitchen open to family room, perfect for entertaining, two story master suite with steam shower, double marble vanity, huge Jacuzzi, two walk in... View all property information
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    Chicago, Illinois 60659
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    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Enjoy a great urban experience staying in the Ukrainian Village of Chicago! -- 2 bedroom flat perfect for short term stays. Convenient to shops, grocery, restaurants, library, bars, gym, swimming pool! THE SPACE: This main floor apartment includes the following amenities: Two comfortable bedrooms... View all property information
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    Chicago, Illinois 60622
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    Lakeview
    3 Bedrooms / 1 Bathroom / Sleeps 10
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    Hey, I have a great apartment available in one of the safest area in Chicago,Wrigleyville! My place is very clean, comfortable and a great fit for you! This unit is in a great location rigth across from wrigley field! It is furnished with nice furniture. A great living room that is very cozy... View all property information
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    Chicago, Illinois 60614
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    2 Bedrooms / 1 Bathroom / Sleeps 3
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    Great 2b, 1 bath apartment in the walkable Ukrainian Village! Close to groceries, restaurants, shopping, clubs, public transportation, and easy access to downtown and the lake frowalk out of your apartment to the garden in the backyard, and enjoy your coffee, or watch the kids playing in the... View all property information
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    Chicago, Illinois 60622
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    The Loop
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Magnificent mile 1 brm convertible apt off Michigan Avenue in hotel district featuring 24 hr doorman, rooftop gym, sundeck, business ctr and garden patio. Your neighbors are the Hyatt, Fairmont and Radisson Blue. Gym, sundeck on rooftop 48th floor. Insane winter reductions!! North side prices in... View all property information
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    Chicago, Illinois 60601
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    Northwest Side
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Live like a native in this artist-owned, artist-occupied vintage building located between the leading edge of the trendy Logan Square restaurant nexus and the old Polish neighborhood. Furnished in rustic Modern finds, it's on the Blue Line with easy access to the Loop and O'Hare. The unit has two... View all property information
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    Location Information
    Chicago, Illinois 60618
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    5 of 5 stars (4) Excellent
    The Loop
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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
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    Location Information
    Chicago, Illinois 60605
    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...
    5 of 5 stars Reviewed August 1, 2014
    We loved the pad, the location, the view, and the city. Would go back to this spot in a heartbeat. The owner was courteous and easy to contact.
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    4 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    About this property
    Welcome! Welcome! Our single family brick house is located in a rare semi-private block about 5 miles West of Downtown. It has 3 Bedrooms, 1 Bathroom, Living Room, Dining Room and Full Kitchen. If you enjoy a quiet home with newer beds, clean sheets and towels, spaces, privacy, kitchen, laundry,... View all property information
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    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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    4.5 of 5 stars (2) Very good
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    About this property
    This is a 3 Bed Room apartment of a two flat brick building in Andersonville area of Chicago. This apt has: 3 bedrooms, sleeps 8 Air Conditioners Free cell phone for international guests (plus deposit) Eat-in Kitchen Living Room Full size fridge Free parking Free laundry Complete kitchen Living... View all property information
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    Chicago, Illinois 60640
    4 of 5 stars Reviewed July 10, 2014
    I really enjoyed staying here. A great property. The sink did break while we were there but Jackie was right on getting it fixed for us! Great place, big enough for our group!
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    5 of 5 stars (2) Excellent
    Lakeview
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Waterfront
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    • Pets allowed
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    • ?
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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
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    Location Information
    Chicago, Illinois 60657
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    4 of 5 stars (5) Very good
    Rogers Park
    2 Bedrooms / 1 Bathroom / Sleeps 7
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    • ?
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    About this property
    This listing is for a private 2-bedroom apartment in the Rogers Park neighborhood of Chicago. The apartment is over 1200 square feet (111 sq meters) and has tall 9.5' ceilings (2.9 meters), a marble bath, and hardwood floors throughout. There is also a charmingly retro yet fully functional kitchen... View all property information
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    Location Information
    Chicago, Illinois 60660
    5 of 5 stars Reviewed January 1, 2015
    Lisa and Caitlin did such an amazing job making the home comfortable and I loved the books about Chicago and the Book they had made with so much helpful information! The location...
    4 of 5 stars Reviewed October 2, 2014
    Three of us stayed at at Devon property and were thrilled with the accommodations. The location to the local bus and train stops were very convenient. The hosts, Lisa and...
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    5 of 5 stars (1) Excellent
    Lakeview
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --133 Reviews Ranked #1 of 51 Specialty Lodging in Chicago! Walk in to the home and the first thing you notice is nothing has been taken for granted. You'll be engulfed in warm inviting hues. The beauty & integrity of... View all property information
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    Chicago, Illinois 60613
    5 of 5 stars Reviewed April 28, 2015
    I traveled to Chicago for a Baptism, meeting family from LA and Boston. We stayed in the Lakeview suite. Teri allowed us to enter the apt. early on the day of our arrival. The...
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    5 of 5 stars (37) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Suitable for children
    • x
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    About this property
    City of Chicago Vacation LICENSE NO.: 2087699 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful tree-lined neighborhood of Andersonville. Located in the FUN, EXCITING, ECLECTIC ANDERSONVILLE Neighborhood on the north side of Chicago less than 2-blocks west of Clark Street... View all property information
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    Location Information
    Chicago, Illinois 60640
    5 of 5 stars Reviewed May 7, 2015
    Love Andersonville. Attractive, quiet & comfortable apartment with amenities and good parking options. Paul very responsive to any questions or concerns. Enjoyable stay. Hope to...
    5 of 5 stars Reviewed March 31, 2015
    This apartment was wonderful. It was clean and accessible to the trains. The parking was great. I was able to find street parking within 1/2 block at all times. The...
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    5 of 5 stars (19) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
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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. Located in Chicago's newest neighborhood - 'SONO', at the... View all property information
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    Chicago, Illinois 60642
    5 of 5 stars Reviewed April 20, 2015
    Traveling to Chicago for a conference with 4 colleagues and rented the Magic Factory for a few nights in early April 2015. Booking was simple and Carole & Basil were great...
    5 of 5 stars Reviewed April 20, 2015
    Beautiful, spacious loft in a convenient location. Our group of 6 stayed for the weekend. We didn't bring our cars, but it was super easy to get around because it's a very...
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    2.5 of 5 stars (2) Poor
    Rogers Park
    3 Bedrooms / 1 Bathroom / Sleeps 8
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    • x
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    • x
    About this property
    Perfect Home while visiting Chicago for a few days or longer stays, perfect for family gatherings, vacation, wedding stays, or simply enjoying time in The city. Walking distance to lots and public transportation! THE UNIT Lots of natural light due to the unit being on the top floor of nice and... View all property information
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    Location Information
    Chicago, Illinois 60626
    1 of 5 stars Reviewed April 15, 2015
    My sister was staying with us on (Apr.7) and opened the door and entered, NO HEAT,beds shabby very low to the floor and frumpy.The house was not up to advertised pictures on the...
    4 of 5 stars Reviewed April 9, 2015
    We like the house, it 's bright, lot of windows,it's a charming older home with hardwood floor.Very good location, walking distance to Loyola University and lake Michigan. There...
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    2 of 5 stars (1) Poor
    Rogers Park
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Hot Tub
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    • x
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    About this property
    The Space Living room and dining room combo. Rooms are nice and cozy, cute and quiet. The unit is located in the East Rogers Park neighborhood of Chicago and border with Edgewater, within walking distance to the CTA Red Line Loyola station, Loyola University, restaurants, coffee shops, Lake... View all property information
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    Chicago, Illinois 60626
    2 of 5 stars Reviewed May 5, 2015
    Place was dark and damp. Bed sheets were clean, but pillows old and flat. Beds are double size. Towels were clean, but bathroom toilet area smelled moldy. Floors not very clean...
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    Northwest Side
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    Available ONLY 12/23/14- 12/29/14 We normally take 2 long vacations and are willing to rent our place. This house is fully furnished with a fully operational kitchen and full use of cooking utensils. Seating for up to 10 at dining room table. This house is best for someone looking to get their... View all property information
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    Chicago, Illinois 60656
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    $150
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    2 Bedrooms / 2 Bathrooms / Sleeps 10
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    Modern 3BD 2Bth Brick-Style Ranch! Sleeps 10!! ASK ABOUT OUR PRICE MATCHING OPTION!! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. -3 Bedrooms -2 Bathroom -Hardwood Floors -Tiled Bathroom -Centrally controlled Heat and Air -Big back yard... View all property information
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    Location Information
    Chicago, Illinois 60162
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    The Loop
    2 Bedrooms / 1 Bathroom / Sleeps 8
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    About this property
    This is a one bedroom loft with the living-room converted into a second bedroom. It has two beds in the bedroom and the living-room has a bunk bed. 800 square feet 32″ Flat-screen TV Wireless Internet-5 MPBS This luxury condominium is conveniently located one block to McCormick Place with easy... View all property information
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    Chicago, Illinois 60616
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    DePaul
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    HISTORY: Aster House has been renting since 1891, and under the present owners since 1982. We've had guests return as long as 18 years, so you may be assured of a safe secure visit. NEIGHBORHOOD: Aster House is on a quiet residential street in Lincoln Park, Chicago's most upscale downtown... View all property information
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    Chicago, Illinois 60614
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    5 of 5 stars (1) Excellent
    Gold Coast, Near North Side
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • x
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    About this property
    First Class Chicago vacation rentals by owner gives you the loveliest choice in Chicago Brownstone vacation rentals. Located in the Gold Coast neighborhood, these brownstones will surpass your expectations for quality and comfort. You will never want for a Magnificent Mile hotel as First Class... View all property information
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    Location Information
    Chicago, Illinois 60611
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    Northwest Side
    3 Bedrooms / 3 Bathrooms / Sleeps 10
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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. My duplex is located in the historic... View all property information
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    Location Information
    Chicago, Illinois 60647
    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.