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Rentals for Seniors in Chicago, IL

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From
$75
Per Night
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1 / 18
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The Loop
Studio, 1 Bathroom, Sleeps 2
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From
$189
Per Night
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1 / 16
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3 Bedrooms, 1 Bathroom, Sleeps 6
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$125
Per Night
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1 / 37
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
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$80
Per Night
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1 / 14
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • 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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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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From
$199
Per Night
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1 / 15
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Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located a block north of the Chicago River this property features a prime location just steps from Michigan Avenue. Amenities include gym, pool, and hot tub. Two queen size beds and a fold out sleeper sofa make it possible to sleep six. Chicago's premier downtown Streeterville neighborhood grants... View all property information
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5 of 5 stars Reviewed January 28, 2015
My fiancé and I really enjoyed ourselves here!! It was everything we were looking for in a nice condo for a mini getaway. We walked right out our condo and BOOM there was...
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$375
Per Night
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1 / 32
Lakeview
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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 and character! A Vintage Beauty With All the Modern Comforts & Amenities.... View all property information
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5 of 5 stars Reviewed July 26, 2014
What a perfect place for a family get away. The Clark Suite was perfect for our family of 7 adults. The kitchen was immaculate and well equipped with anything you needed. I...
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From
$80
Per Night
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1 / 17
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
1100 sq feet of your own space! Lots of room to stretch out here, two bedrooms with queen-sized beds, an office, living room, den, full kitchen, one bathroom, laundry in unit, back deck, backyard with apple tree (apples!!!), Keurig coffee maker, and parking right out front! Queen sized air... View all property information
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5 of 5 stars Reviewed February 8, 2015
This is a two bedroom apartment on the first floor on a quiet street two blocks from Humboldt Park. We arrive in two days after the big blizzard, and the sidewalk was nicely...
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From
$199
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1 / 16
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Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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From
$200
Per Night
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1 / 22
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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 has been taken for granted. You’ll be engulfed in warm inviting hues. The beauty & integrity of the historic homerecaptured; undeniably charming. Glance around... View all property information
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From
$120
Per Night
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1 / 15
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Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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From
$218
Per Night
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1 / 11
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • 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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From
$85
Per Night
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1 / 16
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Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (32) Make Inquiry
Amenities & Details
  • 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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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...
5 of 5 stars Reviewed November 14, 2014
My husband and I rented the apartment for 5 days in early November. I was attending a Conference downtown and did not want to pay the high price hotel. This place was perfect...
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From
$99
Per Night
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1 / 14
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DePaul
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
NOTE This calendar is updated weekly not daily. Please visit www.LincolnParkVacationRentals.com for the most accurate information or email inquiry@lincolnparkvacationrentals.com to inquire about this or our other units at the same location. Please also note that holiday weeks and special event... View all property information
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5 of 5 stars Reviewed July 18, 2012
We first stayed at this holiday rental last summer when visting our son at Depaul university. The location of the rental is good for exploring the lincoln park area and an...
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From
$195
Per Night
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1 / 15
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Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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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From
$237
Per Night
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1 / 10
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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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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From
$99
Per Night
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1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
Suitability
  • 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 apt is very big and had a has a lot of natural sunlight. Located on the first floor of our building. We live upstairs in a completely separate apt so we are very close if you have any questions or concerns, but your privacy is assured.... View all property information
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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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From
$100
Per Night
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1 / 24
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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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From
$100
Per Night
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1 / 20
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Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • 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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From
$100
Per Night
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1 / 18
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Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Nice and bright 2 bedroom 2 bath condominium two blocks from the lake and one block from train, bus, restaurants and coffee shops. Unit is cozy, spacious and conveniently located on first floor, with washer and dryer. Hardwood floors. LOCATION The unit is located on East Rogers Park, two blocks... View all property information
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From
$300
Per Night
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1 / 6
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Avenue. First Floor Condominium Unit, New Oak Floors, Granite Counters, Marble Baths. Stainless Steel Brand New Appliances. In Unit, Washer, Dryer. Three Large Bedrooms. Master Bath... View all property information
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5 of 5 stars Reviewed October 7, 2014
The condo is all that it is advertised. The neighborhood is quiet and the condo is well appointed with all of amenities for you to enjoy your stay. The hardwood floors are a nice...
5 of 5 stars Reviewed June 10, 2014
This condo fit our needs perfectly. My wife and I were staying with our young daughter and going to 3 Cubs games. It was great every night to be able to come back to this place...
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From
$550
Per Night
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1 / 13
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Northwest Side
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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From
$487
Per Night
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1 / 15
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (15) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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From
$623
Per Week
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1 / 40
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The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
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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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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From
$4,100
Per Month
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1 / 19
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Optima is a new building opening in Spring of 2013, towering 42 stories over Michigan Avenue. Sleek design incorporates floor-to-ceiling reflective glass windows and European-designed finishes throughout. The condo features 700 sq. ft. of bamboo flooring, porcelain tile, granite counter tops,... View all property information
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5 of 5 stars Reviewed April 12, 2014
This modern apartment really is 1 minute walk from the mag mile, next door to Inter Continental Hotel (try the wine tasting menu!) also has lake views. A well equipped gym and...
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From
$550
Per Night
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1 / 13
Near North Side
2 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Reviews (3) Make Inquiry
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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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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From
$299
Per Night
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1 / 34
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to Chicago -- far from your typical Chicago rental. The building offers unparalleled amenities, upscale stylish accommodations, and floor-to-ceiling dynamic views of the Chicago skyline. This property is unlike any other in its class and the experience is definitely one-of-a-kind.... View all property information
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5 of 5 stars Reviewed October 21, 2014
El departamento está mucho mejor de lo que se ven en las fotos y vale la pena cada centavo que pagamos por él. Además de la excelente ubicación (está a una cuadra de la avenida...
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From
$200
Per Night
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1 / 10
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The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This is another one of our properties in the South Loop that has amazing amenities and a great feel to it. You will see from the pictures there is a king sized bed along with a sleeper sofa in the loving room which is how this unit can accommodate four people. Please let me know what questions you... View all property information
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From
$299
Per Night
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1 / 30
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Pet: Pet Friendly AVAILABLE JANUARY 29TH!!!!!!!!!!!! Features: 100 sq. ft balcony, grill and patio furniture Newly furnished condo from Room and Board. New appliances Includes new linens, towels All kitchen appliances/table wear/pots and pans 55' LED LCD TV with DVD SURROUND... View all property information
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From
$150
Per Night
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1 / 28
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to Optima Chicago. This building just opened in August of 2013 and has the amenities everyone wants. Indoor pool, rooftop hot tub, indoor basketball court, and more! Your stay here will be nothing short of amazing and you will want to return! View all property information
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From
$250
Per Night
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1 / 10
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
**LOCATION **LOCATION **LOCATION! ***CAN'T BEAT IT! ***Views Views Views! Breathtaking Lake and City Views!!*** Looks Like Hawaii Up There!*** Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep of... View all property information
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5 of 5 stars Reviewed September 2, 2014
We're home from our trip and back to reality! We loved your City and will definitely be back, next time could you arrange a bit better weather please!! But, as Brits we're used to...
5 of 5 stars Reviewed July 22, 2014
We booked through Steps From Everything and they were very easy to work with. The price was very reasonable and the location was great. We could walk two blocks to the Metro...
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From
$4,700
Per Month
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1 / 31
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Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to Optima Chicago. This building just opened in August of 2013 and has the amenities everyone wants. Indoor pool, rooftop hot tub, indoor basketball court, and more! Your stay here will be nothing short of amazing and you will want to return! View all property information
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From
$5,900
Per Month
View Details
1 / 33
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Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
There's a new face on an architectural gem in downtown Chicago and it's Axis Apartments & Lofts. Wrapped in striking lake & city views, this modern high-rise conceals two exceptional living space options within. Live your life from a heightened perspective. Live your life at Axis.... View all property information
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From
$6,600
Per Month
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1 / 21
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The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Pool Table
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
About this property
This building just opened up in July of 2014 and is the most modern building you can find in the Chicago Loop area. From the state of the art amenities to the amazing and helpful staff, you will love staying at this apartment. Located in the Loop you have access to all the tourist attractions as... View all property information
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From
$197
Per Night
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1 / 7
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Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two bedrooms, two bathrooms 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 8 people. FREE Wireless internet access. FREE parking on public street in front of the building.... View all property information
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From
$399
Per Night
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1 / 31
Lakeview
5 Bedrooms, 2 Bathrooms, Sleeps 9
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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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From
$167
Per Night
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1 / 13
Payment Protection
Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two bedrooms, one 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 8 people. FREE Wireless internet access. FREE parking on public street in front of the building. Bus... View all property information
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From
$275
Per Night
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1 / 14
Payment Protection
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Tides is a great way to experience life and culture in the heart of Chicago! Featuring a modern contemporary feel, the short term rentals at The Tides offer dramatic finishes including tiled entries, granite islands and cherry cabinetry, open floor plans with captivating views from the... View all property information
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4 of 5 stars Reviewed February 5, 2015
This apartment is located in a modern, somewhat glitzy group of buildings which form their own mini-village. It is located east of Michigan Ave., almost across the street from...
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From
$205
Per Night
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1 / 12
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Gold Coast, Near North Side
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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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From
$199
Per Night
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1 / 9
Payment Protection
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our 1 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 Tempur-Pedic Mattresses, Cleaning Service... View all property information
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4 of 5 stars Reviewed September 29, 2014
The apartment was more spacious and comfty than it appeared in photos. The location was excellent, we had everything we could need at much 2 blocks away (restaurants, bars...
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From
$315
Per Night
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1 / 32
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Take me to the Penthouse! Stay in our Penthouse Condo on the 50th Floor! A true Penthouse, stunning views of the lake and city. Walk to everything downtown. Upgraded everything. Granite kitchen counter tops, stainless steal appliances, marble in the bathrooms, king size beds, floor to ceiling... View all property information
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5 of 5 stars Reviewed June 30, 2014
Can't sat enough good things about this place. Excellent host, great amenities, perfect location. Top shelf stay.
5 of 5 stars Reviewed August 15, 2011
Was a bit nervous booking the condo vs. a traditional hotel for a group of co-workers. Fantastic accommodations, great view, clean, convenient location. We already re-booked with...
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From
$199
Per Night
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1 / 15
Payment Protection
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our 1 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 Tempur-Pedic Mattresses, Cleaning Service... View all property information
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4 of 5 stars Reviewed September 20, 2012
We rented a one-bedroom apartment in this six-apartment building for the entire summer, so we could experience Chicago without exhausting ourselves. Cozy apartment, comfortably...
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From
$305
Per Night
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1 / 12
Payment Protection
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Apartment - 2 Bedrooms + Convertible bed(s) - 2 Baths - (Sleeps 4-8) Another First Class Chicago property! City of Chicago Vacation Rental License #2125365. Rent Legally! You've found it! Location, Location, Location! An historic 1890's brownstone in the heart of the exclusive Gold Coast where... View all property information
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2 of 5 stars Reviewed August 24, 2014
I waited a while to write this review to ensure it gave the landlord a chance to answer some of the issues that I had with this property however after 3 weeks I have still...
1 of 5 stars Reviewed May 12, 2014
We had very high hopes for a First Class stay during our four-day trip to Chicago over Easter at the 2-bedroom unit in the Gold Coast area to celebrate two special occasions...
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From
$159
Per Night
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1 / 7
Payment Protection
Near North Side
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Experience our amazing, over sized, fully furnished “Old Town Chicago” studio with private balcony 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 Tempur-Pedic... View all property information
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From
$120
Per Night
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1 / 7
Payment Protection
Lincoln Park
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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
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4 of 5 stars Reviewed January 18, 2015
This was our second time staying here. It is less than 5 minutes from our daughter's apartment. and the perfect Lincoln Park location. The apartment was clean, the bed...
4 of 5 stars Reviewed September 29, 2014
The unit is very nice: in a great neighborhood, within walking distance of a huge park, free (world class) zoo, free (world class) conservatory, and very nice business area full...
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From
$315
Per Night
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1 / 12
The Loop
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (9) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Walk to Everything Downtown! Enjoy Stunning Views of the City Skyline and Grant Park! ONE OF FEW 3BD/2.5BA UNITS RIGHT IN THE MIDDLE OF DOWNTOWN CHICAGO. Very affordable! ***WALK TO EVERYTHING ***YES, THESE ARE THE VIEWS! ***BREATHTAKING VIEWS OF THE CITY SKYLINE AND GRANT PARK ***3... View all property information
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4 of 5 stars Reviewed October 30, 2014
This is a superb place to stay. Warm, comfortable with stunning views of downtown and Grant Park. We booked with stepstoeverything and their communications were top class...
5 of 5 stars Reviewed July 18, 2014
Pretty close to downtown parking is across the street Reservation and service are with phone communication, quick and helpful. Keyless entry Recent renovated with quality...
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From
$375
Per Night
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1 / 6
Payment Protection
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Private Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Location. Situated in the heart of Chicago, State and Grand by BridgeStreet 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.... View all property information
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From
$150
Per Night
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1 / 13
Payment Protection
Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Great Old Town 2BR. Very homey and well suited for travelers on business or leisure. Steps away from all public transportation in a area with gorgeous tree lined streets and high end accommodations. The Space Welcome to my 2 bedroom fully furnished “Old Town Chicago” condo. Inside there... View all property information
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4 of 5 stars Reviewed August 18, 2014
I stayed at this apartment for 6 nights in August together with my wife and my two kids. The apartment was big enough for all of us and had almost everything that we needed. The...
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From
$200
Per Night
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1 / 8
Payment Protection
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 5
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The Space The definition of the perfect location. Lincoln Park one of Chicago's most prestigious neighborhoods is central to just about everything! A typical day might start with a trip to Chicago's best farmers market (Green City Market) just a few blocks away. After breakfast spend some time... View all property information
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From
$99
Per Night
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1 / 4
Payment Protection
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Step into this modern loft in the heart of Old Town Corridor only steps from the Brown Line- Sedgwick Stop and all Wells Street has to offer. Hardwood floors throughout with a lofted bedroom overlooking the unit. View all property information
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From
$625
Per Night
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1 / 10
Near North Side
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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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