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Featured Chicago Hotels with Connecting Rooms

See all 1,166 Properties in Chicago
W Chicago - Lakeshore

W Chicago - Lakeshore

644 N Lake Shore Dr, Chicago
  • Free Cancellation
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4.5 out of 5.0
 
 
4.0 out of 5 (2,094 reviews)
The hotel workers were on strike- no cleaning rooms, etc. BUT the concierge, Lois, was wonderful!
Sep 18, 2018

$206 per night for 2 guests

W Chicago - Lakeshore$206
Sheraton Grand Chicago

Sheraton Grand Chicago

301 E North Water St, Chicago
  • Free Cancellation
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4.0 out of 5.0
 
 
4.2 out of 5 (4,262 reviews)
It is close to Michigan Avenue. The only issue was the hotel staff was on strike and out front picketing making tons of noise.
Sep 18, 2018

$239 per night for 2 guests

Sheraton Grand Chicago$239
Hyatt Regency Lisle near Naperville

Hyatt Regency Lisle near Naperville

1400 Corporetum Drive, Lisle
  • Free Cancellation
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3.5 out of 5.0
 
 
4.1 out of 5 (1,484 reviews)
Vacation The only issue I had was they didn't have the 2 double beds that I requested but they did fix my issue by offering an extra room for me extra charge
Jul 3, 2018

$107 per night for 2 guests

Hyatt Regency Lisle near Naperville$107
Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

1800 East Golf Rd, Schaumburg
  • Free Cancellation
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4.0 out of 5.0
 
 
4.1 out of 5 (1,661 reviews)
Excellent Hotel, large rooms, everything has been renovated. Impressive entrance , lobby, conference and banquet rooms. Rooms themselves extremely clean.
Aug 30, 2018

$90 per night for 2 guests

Hyatt Regency Schaumburg Chicago$90
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
  • Free Cancellation
4.0 out of 5.0
 
 
4.2 out of 5 (10,755 reviews)
Weekend in ChicagoMuch to our surprise, the hotel worker's union in Chicago was on strike...so every time we went in and out, we passed the striker's line...which was uncomfortable. This led to few staff at check-in, and even fewer at the lounge Friday evening. We were glad to have checked in at 9:30 pm as we saw ...
Sep 17, 2018

$165 per night for 2 guests

Palmer House a Hilton Hotel$165
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago
  • Free Cancellation
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4.5 out of 5.0
 
 
4.3 out of 5 (2,198 reviews)
The property was great. It was in a great location to access the whole City.
Sep 14, 2018

$233 per night for 2 guests

Fairmont Chicago at Millennium Park$233
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago
  • Free Cancellation
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4.5 out of 5.0
 
 
4.2 out of 5 (2,160 reviews)
Nice hotel. Great locationMany attractions and restaurants within walking distance
Aug 12, 2018

$259 per night for 2 guests

The Westin Michigan Avenue Chicago$259
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St, Chicago
  • Free Cancellation
3.5 out of 5.0
 
 
4.2 out of 5 (4,417 reviews)
Good location. Some construction going on but otherwise clean and neat.
Sep 16, 2018
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

100 W. Monroe St, Chicago
  • Free Cancellation
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4.0 out of 5.0
 
 
4.5 out of 5 (1,133 reviews)
Good hotel, excellent location.Nice hotel, most importantly clean, comfortable. Could have used more storage space.
Aug 23, 2018

$229 per night for 2 guests

Hyatt Centric The Loop Chicago$229
Hyatt Place Chicago/Lombard/Oak Brook

Hyatt Place Chicago/Lombard/Oak Brook

2340 South Fountain Square Drive, Lombard
  • Free Cancellation
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3.0 out of 5.0
 
 
4.4 out of 5 (1,638 reviews)
I loved the location. So close to so many restaurants, including several very fine ones within walking distance. It's in a upscale area that felt extremely secure. I will be making this my go to hotel for all my future Chicagoland visits.
Sep 3, 2018
Chicago Athletic Association

Chicago Athletic Association

12 South Michigan Avenue, Chicago
  • Free Cancellation
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4.5 out of 5.0
 
 
4.6 out of 5 (1,277 reviews)
Bridget at front desk, extremely helpful, Cindy’s rooftop staff also very helpful for next day reservations, this is a landmark hotel in Chicago. Wonderful location on Michigan Avenue.
Sep 15, 2018

$229 per night for 2 guests

Chicago Athletic Association$229
Wyndham Grand Chicago Riverfront

Wyndham Grand Chicago Riverfront

71 E Wacker Dr, Chicago
  • Free Cancellation
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4.0 out of 5.0
 
 
4.4 out of 5 (6,944 reviews)
Excellent downtown hotel in Chicago Upgraded to suite so no complaints there. The only negative was that the room was difficult to heat. Very handy location, very friendly., attentive staff.
Sep 14, 2018

$175 per night for 2 guests

Wyndham Grand Chicago Riverfront$175
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10 E Grand Ave, Chicago
  • Free Cancellation
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3.0 out of 5.0
 
 
4.3 out of 5 (2,006 reviews)
Good place to stay downtownEasy walk to many places, friendly, helpful staff, fun views out our window. We used the coffeemaker and refrigerator each day, and hot tub was nice to use after being on the go all day.
Jun 25, 2018
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

540 North Michigan Avenue, Chicago
  • Free Cancellation
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4.0 out of 5.0
 
 
4.1 out of 5 (1,819 reviews)
Staff were pleasant and professionalAlthough busy, the hotel was a pleasant experience
Sep 3, 2018
AmericInn by Wyndham Schaumburg

AmericInn by Wyndham Schaumburg

1300 E Higgins Rd, Schaumburg
  • Free Cancellation
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3.0 out of 5.0
 
 
4.2 out of 5 (1,379 reviews)
Great location in Schaumburg!We were booked for 2 nights and had to check out by about 6pm on the 2nd night, as the bed was totally uncomfortable for me. I am handicapped and the bed was too firm, especially since I can only sleep on one side all night - I ended up with such a backache, that we had to leave for home before we ...
Sep 18, 2018

$79 per night for 2 guests

AmericInn by Wyndham Schaumburg$79
Embassy Suites Chicago Downtown

Embassy Suites Chicago Downtown

600 N State St, Chicago
  • Free Cancellation
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4.0 out of 5.0
 
 
4.4 out of 5 (3,623 reviews)
Great Hotel! Great Location!Great hotel within walking distance of shopping and restaurants. Checking in and out was a breeze. We arrived early, but was able to check-in anyway.
Aug 25, 2018

$169 per night for 2 guests

Embassy Suites Chicago Downtown$169
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago
  • Free Cancellation
3.5 out of 5.0
 
 
4.3 out of 5 (1,814 reviews)
Great location, good amenities. The suite was well worth the money
Sep 19, 2018
Hyatt Place Chicago/ Schaumburg

Hyatt Place Chicago/ Schaumburg

1851 McConnor Parkway, Schaumburg
  • Free Cancellation
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3.0 out of 5.0
 
 
4.2 out of 5 (1,621 reviews)
Property location was perfect. Nice business district area with shopping and restaurants nearby.
Sep 17, 2018

$82 per night for 2 guests

Hyatt Place Chicago/ Schaumburg$82
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

633 N Saint Clair St, Chicago
  • Free Cancellation
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4.0 out of 5.0
 
 
4.5 out of 5 (2,357 reviews)
Lovely hotelThe hotel is in a great location. Easy walking distance to resturants and shops. Our room was large and very clean. Grest tea and coffee maker! Staff were very helpful.
Aug 29, 2018
AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

630 N Rush St, Chicago
  • Free Cancellation
  • Reserve now, pay when you stay
3.5 out of 5.0
 
 
4.3 out of 5 (1,935 reviews)
Good hotel with very helpful staff. Good hotel with very helpful staff and close to Magnificent Mile. Provides good self service breakfast. Rooms are comfortable and spacious. Recommend this hotel.
Jul 21, 2018
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Recently booked Hotels with Connecting Rooms in Chicago

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Pocket Guide: Hotels with Connecting Rooms in Chicago

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