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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 (2) Excellent
    Northwest Side
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    1 / 7
    4 of 5 stars (7) 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 stars Reviewed August 10, 2015
    Stayed in the LPA location this past weekend and enjoyed the area tremendously. You have a park across the street and zoo just mins. down the road. The apartment itself is a cozy...
    4 of 5 stars Reviewed July 13, 2015
    Located across from Lincoln Park Zoo & Conservatory, this is an ideal location for a couple, or a family of 3. The apartment is on the 4th floor and features a large living room...
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    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
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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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
    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
    1 / 14
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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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 / 32
    5 of 5 stars (4) Excellent
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR>Welcome to the LEX... View all property information
    Location Information
    Chicago, Illinois 60616
    5 of 5 stars 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 stars 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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    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    This condo, located on Lake Shore Dr. is in the prestigious east Lincoln Park and hip Lakeview area. It has scenic views of Lake Michigan and Belmont Harbor from both the bedroom and living room. A few blocks away from Broadway Street and its stretch of restaurants, bistros, and nightlife. Steps... View all property information
    Location Information
    Chicago, Illinois 60657
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    1 / 40
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Ref # 369697 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. If you are looking for a spacious 2,000sq fully furnished condo with brand new floors,... View all property information
    Location Information
    Chicago, Illinois 60653
    1 / 29
    5 of 5 stars (1) 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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    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 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 / 19
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 360046 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. Travelling to Chicago is no hassle as you can stay in this luxurious and furnished one... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 26
    5 of 5 stars (1) Excellent
    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Sauna
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
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    • ?
    About this property
    Unit not available for daily rental in July 4th Holiday !<BR><BR><BR>*Prices may vary depending on the season. Premium months are between April and September. <BR>*Prices negotiable based on length of stay. Please inquire and we will provide a direct quote for your stay.<BR><BR><BR>Michigan Avenue... View all property information
    Location Information
    Chicago, Illinois 60616
    5 of 5 stars 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 / 21
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Ref # 359720 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Experience luxury in Chicago by staying in this wonderful one bedroom condominium that... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 8
    4 of 5 stars (3) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • x
    About this property
    One of three spacious apartments in a multi-flat historic building, located in the true artist oriented neighborhood in the heart of Chicago. Large kitchen space and a full newly remodeled bath with Jacuzzi tub and beautiful Moroccan tile. Cozy dinning room and sunny living room each with... View all property information
    Location Information
    Chicago, Illinois 60608
    5 of 5 stars Reviewed 1 week ago
    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 1 week ago
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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 / 7
    5 of 5 stars (3) Excellent
    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 stars Reviewed 1 week ago
    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 / 20
    4 of 5 stars (1) Very good
    Lakeview
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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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 Soft Towels, coffee and tea as well as everything you need to cook for a longer... View all property information
    Location Information
    Chicago, Illinois 60657
    4 of 5 stars 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 / 9
    The Loop
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 372626 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. Marquee at Block 37 is a brand new, full-amenity building located just two blocks from... View all property information
    Location Information
    Chicago, Illinois 60601
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    1 / 11
    5 of 5 stars (1) Excellent
    Northwest Side
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
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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
    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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    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
    1 / 38
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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 1.5 bedroom, 1 bathroom loft in Chicago. Modern... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 36
    4 of 5 stars (1) Very good
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Experience our 2 bedroom fully furnished “Old Town Chicago” condos designed by famous Chicago artist Edgar Miller (The Chicago Renaissance Man) with Flat Panel HDTVs, Fireplaces, All Utilities, All Major Appliances, WiFi, Internet, Cable, Queen Size Mattresses, Cleaning Service Included,... View all property information
    Location Information
    Chicago, Illinois 60610
    4 of 5 stars Reviewed October 24, 2015
    We chose this property for the Chicago marathon weekend - so glad we picked here as for marathon spectating it couldn't have been better. In fact, the location was great all round...
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    1 / 5
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 364653 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. Furnished studio in Gold Coast area, 2 twin beds or a King, cable TV, wireless... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 33
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Ref # 360346 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. Enjoy staying in this cool and comfortable studio loft with exposed brick which has a... View all property information
    Location Information
    Chicago, Illinois 60610
    1 / 16
    Near North Side
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Ref # 361752 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 amazing apartment has all the luxuries of home. It has been beautifully furnished... View all property information
    Location Information
    Chicago, Illinois 60611
    The Loop
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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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.<BR>800 square feet<BR><BR>32″ Flat-screen TV<BR>Wireless Internet-5 MPBS<BR><BR>This luxury condominium is conveniently located one block to McCormick... View all property information
    Location Information
    Chicago, Illinois 60616
    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
    • Child-friendly
    • ?
    • ?
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    • 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
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 1 week ago
    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 2 weeks ago
    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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    DePaul, Lincoln Park
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    PLEASE NOTE: This is not a new property. We have recently left our previous management company, which had been managing this and our other 6 properties for 2+ years. Please see photos for past reviews! Our historic Lincoln Park apartment features: 4 bedrooms and 2 baths Sleeping for 8 Premier... View all property information
    Location Information
    Chicago, Illinois 60614
    1 / 13
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Ref # 359743 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Experience luxury in Chicago by staying in this wonderful one bedroom condominium that... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Ref # 361990 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. 38 Unit brick building. This HomeSuite property comes fully furnished and has at least... View all property information
    Location Information
    Chicago, Illinois 60623
    1 / 7
    3.5 of 5 stars (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    About this property
    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 floors . Kitchenette with essentials (cable TV, Computer with wireless... View all property information
    Location Information
    Chicago, Illinois 60608
    4 of 5 stars Reviewed 5 days ago
    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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    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    About this property
    This 60-story sleek skyscraper in the loop is very classy and chic. It is located in the downtown loop area, and borders the Chicago River. The beautiful new skyscraper is situated next to numerous restaurants, nightlife spots, and shopping. This full 1br condo has a modern and clean feel, and... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 17
    The Loop
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 360100 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. Travelling to Chicago is no hassle as you can stay in this luxurious and furnished one... View all property information
    Location Information
    Chicago, Illinois 60601
    1 / 39
    4.5 of 5 stars (18) Very good
    Northwest Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Shared Yard
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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
    4 of 5 stars Reviewed 1 week ago
    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 1 week ago
    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 / 30
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This beautiful unit features Eastern views of the Chicago skyline, including Willis (Sears) Tower. White quartz countertops, two-tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplash Full size washer/dryer Custom designed wide plank flooring... View all property information
    Location Information
    Chicago, Illinois 60607
    1 / 21
    5 of 5 stars (1) Excellent
    Lakeview
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Shared Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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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    Northwest Side
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Two bedrooms, two bathroom condo apartment on the north side of Chicago. The apartment can accommodate 4 guests comfortably, but if need be can add two inflatable mattresses to accommodate up to 6 people. FREE Wireless internet access. FREE parking on public street in front of the building. Bus... View all property information
    Location Information
    Chicago, Illinois 60618
    1 / 10
    5 of 5 stars (3) Excellent
    Roscoe Village
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • Washer
    • Satellite TV
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Make our apartment the perfect home base for your family vacation or romantic getaway to Chicago. There is plenty of room to spread out and enjoy yourselves. The house is beautifully furnished and stocked with all of the essentials. The apartment is an easy walk to multiple bus and train lines,... View all property information
    Location Information
    Chicago, Illinois 60618
    5 of 5 stars Reviewed 2 weeks ago
    Very clean, modern, and responsive owner. It is located in a nice neighborhood that is close to public transportation.
    5 of 5 stars Reviewed August 7, 2015
    We needed a place to stay in Chicago close to family. This rental was perfect. There was more than enough room for 5 of us. It was extremely clean and very nicely decorated...
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    1 / 21
    5 of 5 stars (2) Excellent
    Northwest Side
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Terrace
    • Patio
    • Housekeeping...
    • Washer
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    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 stars Reviewed 2 weeks ago
    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...
    5 of 5 stars Reviewed March 17, 2016
    My family and I enjoyed 3 nights in this lovely home. It's a wonderful location with easy access to O'hare via the train. The house is beautifully decorated and clean. We really...
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    1 / 31
    Lakeview
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 360326 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Have a fantastic stay in Chicago by staying in this gorgeous three bedrooms apartment.... View all property information
    Location Information
    Chicago, Illinois 60613
    1 / 6
    3.5 of 5 stars (3) Average
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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 / 8
    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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 / 30
    5 of 5 stars (37) Excellent
    Northwest Side
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Chicago, Illinois 60625
    5 of 5 stars Reviewed 1 week ago
    I absolutely loved this place, from the emails I sent to Cheryl ( with her quick responses) to the condo itself. Everything was as advertised. The place was spotless, the little...
    5 of 5 stars Reviewed August 19, 2015
    The owner thought to provide everything you might need. Little things like a few snacks and a fan in the bedroom made the place welcoming from start to finish. Large den space...
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    1 / 12
    5 of 5 stars (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • Washer
    • Waterfront
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Elegant 1 bedroom apartment on N Lake Shore Drive,10 min away from Michigan Avenue, Northwestern Memorial Hospital, 25 min by bus to Millenium Park and the Art Institute. Fully furnished, 900 sq ft,beautiful oak floors, high ceilings, custom architectural details.Perfect residential accommodations... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars 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 stars Reviewed December 8, 2011
    My friend and I were blown away by this apartment, beautifully accomodation and accessible to the city with 3 regular buses passing by. The owner was very helpful and...
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    1 / 11
    Northwest Side
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 361759 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. Enjoy tranquil moments in this furnished two bedroom condo in Chicago. This unit has... View all property information
    Location Information
    Chicago, Illinois 60630
    1 / 19
    Near North Side
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • DVD Player
    • Shared Outdoor Pool...
    • Washer
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Stunning Space Features wall to wall upgraded plush carpeting, beautiful open kitchen with granite countertops and stainless steel appliances, massive walk in closet with loads of storage space, floor to ceiling windows exposing eastern peak-a-boo lake views, beautifully updated bathroom, and w/d... View all property information
    Location Information
    Chicago, Illinois 60611
    1 / 25
    5 of 5 stars (1) Excellent
    Lakeview
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Balcony
    • Patio
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! Beautifully furnished and fully equipped--guaranteed a unique and unforgettable experience for you, your family and friends. Rest... View all property information
    Location Information
    Chicago, Illinois 60613
    5 of 5 stars Reviewed December 23, 2015
    Stayed in this house for three nights and had family come in for Christmas get together. It was absolutely perfect. The home is very well maintained with all of the personal...
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    Near North Side
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    ENTIRE SPACE This is an ideal location for visitors. This is modest but nice and completely private studio condo in the Gold Coast located near Water Tower Place, the Hancock Tower, and the Museum of Contemporary Art. It’s 1/2 block from the public transportation stop ( trains and buses), 4 blocks... View all property information
    Location Information
    Chicago, Illinois 60610
    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.