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Featured Chicago Adventure Hotels

See all 1,283 Properties in Chicago
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago
Free Cancellation
4.2/5 (11,028 reviews)
$197/ nightfor 2 guests

I enjoyed my stay here and it's a lovely property, however I was traveling on business and it was very difficult to work because the Wifi continually cut out.

Reviewed on Nov 16, 2018
Hyatt Regency McCormick Place
Hyatt Regency McCormick Place
4.0 out of 5.0 2233 S Martin Luther King Dr, Chicago
Free Cancellation
4.4/5 (3,868 reviews)
$104/ nightfor 2 guests

Concierge bellhop and staff very helpful and polite

Reviewed on Nov 14, 2018
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 out of 5.0 151 East Wacker Dr, Chicago
Free Cancellation
4.4/5 (10,045 reviews)
$115/ nightfor 2 guests

Convenience to family, friends, events and restauranta

Reviewed on Nov 16, 2018
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5.0 323 E Wacker Dr, Chicago
Free Cancellation
4.4/5 (4,036 reviews)
$85/ nightfor 2 guests

Staff were very nice to converse with. - Interested in your why your in the city, provides info about the city but understands when you're in a rush Modern look, clean, timely service, and pleasant atmosphere.

Reviewed on Nov 17, 2018
Hilton Chicago- Michigan Ave Cultural Mile
Hilton Chicago- Michigan Ave Cultural Mile
4.0 out of 5.0 720 S Michigan Ave, Chicago
Free Cancellation
4.2/5 (5,095 reviews)
$119/ nightfor 2 guests

The staff is wonderful, truly engaged and willing to make your stay as comfortable as possible.

Reviewed on Nov 17, 2018
Wyndham Grand Chicago Riverfront
Wyndham Grand Chicago Riverfront
4.0 out of 5.0 71 E Wacker Dr, Chicago
Free Cancellation
4.4/5 (7,077 reviews)
$116/ nightfor 2 guests

Nice hotel in the heart of Chicago. Quick walk to anything you need.

Reviewed on Nov 16, 2018
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5.0 221 N Columbus Dr, Chicago
Free Cancellation
4.5/5 (1,745 reviews)
$125/ nightfor 2 guests

Wonderful hotel but be aware not to get a room that is above the local fire Dept station. Sirens through the night making connected sleep impossible. Opt for south facing rooms.

Reviewed on Nov 18, 2018
HI Chicago
HI Chicago
1.5 out of 5.0 24 East Congress Parkway, Chicago
Free Cancellation
4.3/5 (1,252 reviews)
$65/ nightfor 2 guests

proximity to downtown, really centralised. it is very cleaned, peaceful and well organised. The complimentary breakfast was excellent.

Reviewed on Nov 17, 2018
Hyatt Place Chicago/River North
Hyatt Place Chicago/River North
3.0 out of 5.0 66 W Illinois St, Chicago
Free Cancellation
4.5/5 (2,403 reviews)
$104/ nightfor 2 guests

Rooms were large with great views. Good area close to shops and restaurants. Housekeeping was unobtrusive but thorough. Negatives: fire station 2 blocks down makes for lots of sirens but room came equipped with white noise machine. Gym was relatively small.

Reviewed on Nov 12, 2018
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent Mile
4.0 out of 5.0 633 N Saint Clair St, Chicago
Free Cancellation
4.5/5 (2,418 reviews)
$100/ nightfor 2 guests

The staff was very nice. Big and Clean rooms. Definitely coming back.

Reviewed on Nov 14, 2018
Sheraton Grand Chicago
Sheraton Grand Chicago
4.0 out of 5.0 301 E North Water St, Chicago
Free Cancellation
4.2/5 (4,386 reviews)
$107/ nightfor 2 guests

Great spacious facilities. Was attending a large conference. Would prefer coffee to be available at 5.30am ( am aware of coffee maker in room). Gym is spacious, however there is a need for lighter free weights, e.g. 3 lb, and bigger exercise balls. Overall the gym is terrific. Lighting is the room ...

Reviewed on Nov 5, 2018
Hotel Versey Days Inn by Wyndham Chicago
Hotel Versey Days Inn by Wyndham Chicago
3.0 out of 5.0 644 West Diversey Parkway, Chicago
Free Cancellation
4.2/5 (3,273 reviews)
$71/ nightfor 2 guests

We enjoyed the upbeat vibe the moment you walked through the doors.

Reviewed on Nov 14, 2018
Club Quarters Hotel, Central Loop
Club Quarters Hotel, Central Loop
4.0 out of 5.0 111 West Adams Street, Chicago
4.3/5 (6,290 reviews)
$85/ nightfor 2 guests

Great location. Friendly staff. Short walk to Union Station which works perfectly for me. Will stay here again if government rate is available.

Reviewed on Nov 18, 2018
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 out of 5.0 10 S Wabash Ave, Chicago
Free Cancellation
4.6/5 (5,017 reviews)
$104/ nightfor 2 guests

Great location, staff, and room. Check in and out were easy and staff was friendly.

Reviewed on Nov 18, 2018
Kinzie Hotel
Kinzie Hotel
4.0 out of 5.0 20 W Kinzie St, Chicago
Free Cancellation
4.5/5 (4,197 reviews)
$101/ nightfor 2 guests

This was the second time my party of 4 people stayed at the Kinzie while on an overnight trip to Chicago on the Amtrak to see a musical on the Broadway of Chicago. The hotel is lovely and the staff pleasant and accommodating at every turn. Even after check out, we were allowed to leave our bags there ...

Reviewed on Nov 19, 2018
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4.0 out of 5.0 701 North Michigan Avenue, Chicago
Free Cancellation
4.1/5 (9,460 reviews)
$76/ nightfor 2 guests

The hotel staff was very nice. Very close to all of the shopping and great restaurants.

Reviewed on Nov 19, 2018
Chicago Athletic Association
Chicago Athletic Association
4.5 out of 5.0 12 South Michigan Avenue, Chicago
Free Cancellation
4.6/5 (1,328 reviews)
$132/ nightfor 2 guests

Great property and location. Right across from Millennium Park. Staff friendly and helpful. Definitely recommend. Two suggested areas of improvement: 1) elevator maintenance as one was always down and waited 15 minutes to get to room. 2) no coffee maker in room. Provided upon request but maid service ...

Reviewed on Nov 18, 2018
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5.0 1100 S Michigan Ave, Chicago
Free Cancellation
4.2/5 (1,390 reviews)
$60/ nightfor 2 guests

The room was really dry and the heater was really loud. Front desk was really helpful! Sherry and Octavio were very welcoming!

Reviewed on Nov 15, 2018
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Recently booked Adventure Hotels in Chicago

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Chicago Adventure Hotel Guide

Chicago isn’t just for city slickers anymore. For those who love the great outdoors, there’s much to see and do in the Windy City. During warm weather, jet ski or leisurely paddleboard on Lake Michigan. Take in the scenery of the city by going on a hike through Lakeshore Path, or even book a Segway tour through Grant Park. After soaking up the natural beauty of this Illinois city, return to your comfortable Chicago adventure sport hotel. Nothing makes you appreciate nature’s beauty more than climbing into a soft bed after a long day of hiking.

At Expedia, we want to help you book a one-of-a-kind trip. We can even connect you to specialty boutique hotels in Chicago which fulfill your needs and fit your budget. We compile all the top Chicago hotel offers into one convenient location right here so you can have your pick. Whether you’re spending the day shopping at Magnificent Mile or inner-tubing in Lake Michigan, you can take a load off knowing you paid the best price possible on your adventure sport hotel.