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Luxury Rentals in Chicago, IL

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    $1,350
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    1 / 49
    Lakeview
    11 Bedrooms, 6 Bathrooms, Sleeps 21 | Quick View
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    1 / 55
    Northwest Side, Wicker Park / Bucktown
    3 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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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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    1 / 37
    Lakeview
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    CHICAGO GUEST HOUSE Tripadvisor Certificate of Excellence 2014 5.0 of 5 stars --128 Reviews on TRIPADVISOR Ranked #1 of 51 Specialty Lodging in Chicago! ************************* Beautiful & Spacious--Filled With Charm & Character! The Guest House on Newport Avenue has two apartments in the... View all property information
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    1 / 10
    5 of 5 stars (2) Excellent
    Near North Side
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is the stuff dreams are made of. Towering 54 floors above the city, with dramatic two-story living areas and exquisite fireplace, this Penthouse gives you the ultimate city living. It's all about the views and location. From 25 foot floor to ceiling windows, the city unfolds before your very... View all property information
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    5 of 5 stars Reviewed August 12, 2011
    The location was perfect for our needs - we walked to all the restaurants, bars and stores. Parked the car and didn't move it until we left. Beautifully decorated and furnished...
    5 of 5 stars Reviewed August 12, 2011
    The location was great it was within walking distance to the Chicago Theater, many restaurants, and bars. I would recommend the hop-on and hop-off bus tour which is two blocks...
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    1 / 12
    Near North Side
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The Penthouse at Grand Plaza is a magnificent unique rental in Chicago. Towering 56 floor above the city, with dramatic two story living areas and exquisite fireplace, this Penthouse gives you the ultimate in city living. It's all about the views and location. From 20 foot floor to ceiling windows... View all property information
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    1 / 24
    Lakeview
    6 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Chicago Vacation Rental lenience # 2320200 This well kept property sleeps 14 comfortably with space for two to four more on pull out couches. Enjoy the nice open one level floor plan and sunny interior. Additional bonus includes a a huge patio/ lounge with grill and garden. Between the... View all property information
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    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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. NEW PICTURES COMING SOON 800 square feet Sleeps 6 32″ Flat-screen TV Wireless Internet-5 MPBS This luxury condominium is conveniently located with... View all property information
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    1 / 11
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Gym
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    • Sauna
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    About this property
    Welcome to the luxury and tranquility of the Chicago Penthouse Suite, a rental residence with elegant condominium-quality interiors. The suite boasts 9.5' ceilings, floor to ceiling windows, a private balcony with grill, granite bath and kitchen, beautiful cabinetry, and stainless steel kitchen... View all property information
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    $575
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    1 / 23
    5 of 5 stars (17) 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. Located in Chicago's newest neighborhood - 'SONO', at the... View all property information
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    5 of 5 stars Reviewed November 24, 2014
    We stayed during the Chicago marathon. The apartment is very conveniently located to the subway so that we could get everywhere we needed to during our stay. My favorite part of...
    5 of 5 stars Reviewed November 24, 2014
    My friends made all the arrangements on where to stay and they couldn't have picked a better place. I loved the location and the living space we had. I am not much of a writer...
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    • Suitable for children
    • x
    • x
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    About this property
    This unit is unique because we offer 'Luxury At It's Best'. In addition, we offer luxury & exotic features at a Premium level that you won't get anywhere within the downtown area. All guest have access to all amenities excluding dancing pole and bar area. Both can be purchased at an additional... View all property information
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    1 / 18
    DePaul
    4 Bedrooms, 4 Bathrooms, Sleeps 24 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
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    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
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    About this property
    Temporarily live in the best neighborhood in Chicago in an amazing Furnished Custom Single Family Home. This home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2 blocks to grocery stores, etc, etc. Everything you need is here! This is a top of the line... View all property information
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    1 / 13
    4.5 of 5 stars (3) Very good
    Near North Side
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Overview Reviews (3)
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    • Pets allowed
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    • x
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    About this property
    This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with dramatic two story living areas and exquisite fireplace, this Penthouse gives you the ultimate in city living. It's all about the views and location. From 20 foot floor to ceiling windows the city unfolds... View all property information
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    5 of 5 stars Reviewed July 21, 2013
    We had a group of 6 ranging in age from 16 to 85. We had all looked at the pictures on line but were still blown away when we entered. Furnishings are beautiful and the views are...
    5 of 5 stars Reviewed December 28, 2012
    This penthouse is at the heart of everything. It is a very short walk from Michigan Ave., not to mention all to see on State Street. The views from the penthouse are...
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    1 / 19
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with dramatic two story living areas and exquisite fireplace, this Penthouse gives you the ultimate in city living. It's all about the views and location. From 20 foot floor to ceiling windows the city unfolds... View all property information
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    $550
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    • x
    About this property
    The Hotel Blake*, situated in downtown Chicago's urban Printer's Row district, offers a relaxing retreat and easy access to everything the city has to offer. Unwind in your spacious accommodations, complete with soaring ceilings, exquisite bathrooms and stunning city views. Each room is designed... View all property information
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    About this property
    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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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Grill
    • Hot Tub
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    This unit is unique because we offer 'Luxury At It's Best'. In addition, we offer luxury & exotic features at a Premium level that you won't get anywhere within the downtown area. All guest have access to all amenities excluding dancing pole and bar area. Both can be purchased at an additional... View all property information
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    $500
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    1 / 24
    4.5 of 5 stars (7) Very good
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Water Views
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    • Wheelchair access
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    About this property
    Beautiful B & B Boatel Yacht - Pier Gold offers Chicago visitors a great alternative to regular hotel stays. Located at Chicago's most sought after harbor in the heart of our city waterfront; at Burnham Harbor you will enjoy waking up at your floating waterfront boatel at our harbor with stunning... View all property information
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    4 of 5 stars Reviewed July 31, 2014
    This was absolutely a great choice for a buddy and I to hang out in Chicago for a long weekend. The location was incredible and fortunately for so was the weather. Having done...
    5 of 5 stars Reviewed August 8, 2013
    A short walk (about a block) from the museums you find yourself in the quiet Burnham Harbor and on you very own Yacht! Two very private cabins, a comfortable living area with...
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    1 / 17
    DePaul
    4 Bedrooms, 4 Bathrooms, Sleeps 24 | Quick View
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    • Balcony
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    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Vacation in the best neighborhood in Chicago in this amazing Furnished Custom Single Family Home. This home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2 blocks to grocery stores, etc, etc. Everything you need is here! This is a top of the line... View all property information
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    1 / 10
    4.5 of 5 stars (17) Very good
    Lincoln Park
    4 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    We bought this home because of its proximity to everything the city has to offer while still maintaining the feeling of a small village. It is a village adjacent to all the culture, theatres, shopping, and restaurants that make Chicago a world-class city. We also loved being able to walk or ride... View all property information
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    5 of 5 stars Reviewed March 9, 2015
    We had my brothers bachelor party in Chicago and stayed here this past weekend and had an awesome time! We had 11 people and it was plenty big for all of us. The owner was very...
    5 of 5 stars Reviewed January 26, 2015
    Staying at this property was a dream come true. I had a large group of friends I needed to accommodate and Patti was very responsive and understanding. The house was very clean...
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    $487
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    • Suitable for children
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    About this property
    Book Now for ALL INCLUSIVE BUDGET PACKAGE at a unique and beautifully decorated Bed & Breakfast inn. Stay on our third floor apartment with a shared bath and accommodations for up to 6-9 travelers - Full Size Refrigerator, Huge Leather Couch, Dinette Set, Massage Chair, Air Hockey Table and so... View all property information
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    5 of 5 stars Reviewed April 13, 2013
    We were visiting Chicago for accepted students' visit days at University of Chicago and wanted to stay somewhere close to the university that wasn't a Ramada Inn type hotel...
    4 of 5 stars Reviewed December 7, 2012
    We enjoyed our stay at Welcome Inn Manor B and B. Mel and his assistant were very hospitable, and always started our day off with a hearty and tasty breakfast. Mel is at the ready...
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    $466
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    1 / 27
    5 of 5 stars (19) Excellent
    Overview Reviews (19)
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    • Grill
    • Internet Access
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    • Smoking allowed
    • Suitable for children
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    • x
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    About this property
    Want to live like a local while staying in Chicago and save? Reserve now and take advantage of discounted rates this fall! Our Chicago vacation rental offers an affordable and comfortable place to lay your head during your visit to our city! A family-owned, Chicago boutique vacation rental... View all property information
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    5 of 5 stars Reviewed September 3, 2014
    Every aspect was wonderful. Great location. Easy to get into downtown. Great staff. Beautiful and luxurious condo/home.
    5 of 5 stars Reviewed July 8, 2014
    Brand new. Friendly staff. Helpful. Restaurants close by we're awesome. Used as a running base to lakeshore 1.25 miles. And also less than two miles to Wrigley.
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    About this property
    Enjoy this newly completed high-end renovation of a classic Brownstone home with 5 spacious bedrooms, 3 full baths and home theater equipped living rooms. This beautiful home is located on a quiet, tree lined street on the Northside of Chicago. Located in the Lincoln Square neighborhood, there are... View all property information
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    1 / 32
    5 of 5 stars (26) Excellent
    The Loop
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (26)
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    • Gym
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    • Suitable for children
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    About this property
    Brand new luxury 2 bedroom 2 bathroom corporate housing suite with panoramic views in a building unlike anything in Chicago!! The Resort is located in Chicago's high end neighborhood, Lakeshore East, where the Chicago River meets Lake Michigan. You will enjoy exclusive access to two full-floors... View all property information
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    5 of 5 stars Reviewed September 2, 2013
    We arrived to a great welcome from Nadiya - everything was very straightforward and well organised. The apartment is superb, with terrific lakeside views and is very well...
    5 of 5 stars Reviewed March 14, 2013
    The suite was beautiful... from the furnishings, the view, the amenities, and a few surprise items! Underground free parking was a big plus. Location was perfect. Walking...
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    1 / 7
    The Loop
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautifully done high-end furnished 3 bedroom | 2 bath | located downtown Chicago Beds: 1 King Bed, 2 Queen Beds View all property information
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    $400
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    About this property
    This unit is located in one of the best neighborhoods in downtown Chicago. Studio apartment with 2 full size beds and one bathroom. Sleeps 5 32″ Flat-screen TV Wireless Internet-5 MPBS ENTIRE SPACE (More pictures coming soon) This is an ideal location for visitors. This is unique nice and... View all property information
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    1 / 31
    Lakeview
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Smoking allowed
    • Suitable for children
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    • Elder access
    • x
    About this property
    Beautiful & Spacious! Vintage Charm 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 the historic Greystone recaptured; undeniably charming. Glance around and you’ll see large, colorful... View all property information
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    1 / 6
    Near North Side
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Private Indoor Pool
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    • x
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    About this property
    Location. Situated in the heart of Chicago, this lovely building is within walking distance of American Medical Association Headquarters, Wrigley Building, and Tribune Tower. Also nearby are Hancock Tower and Millennium Park. Property Features. The front desk is open 24 hours a day. Guest... View all property information
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    $395
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    1 / 10
    DePaul
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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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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    1 / 34
    Lincoln Square
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    • x
    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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