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Featured Chicago Adventure Hotels

See all 1,473 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 (11,471 reviews)
$86/ night for 2 guests

Every one was exceptionally friendly. Some miss communication regarding parking. Before heading to hotel, I had made multiple calls regarding late checkout and parking. Unfortunately transferred a number of times and received different answers. Staff should be on same page. The Palmer House is a ...

Reviewed on Feb 15, 2019
RecreationHistoricalConcierge
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 (3,992 reviews)
$123/ night for 2 guests

Great location, super efficient staff, clean and quiet room. We stayed in town for the auto show and loved the proximity to the show - when done, just walk upstairs! The room was extremely quiet and the staff checked us in in under two minutes. Overall a great experience, the only thing that we felt ...

Reviewed on Feb 15, 2019
RecreationSportsConcierge
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 out of 5.0 151 East Wacker Dr, Chicago
Free Cancellation
4.4/5 (10,374 reviews)
$119/ night for 2 guests

It was a wonderful hotel for the price we pay. Very good location, not to busy. Great.

Reviewed on Feb 12, 2019
RecreationFitness CenterSports
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5.0 323 E Wacker Dr, Chicago
Free Cancellation
4.4/5 (4,163 reviews)
$159/ night for 2 guests

The rooms are spacious, the staff is friendly and very courteous. The best end restaurant in the hotel is top notch.

Reviewed on Feb 11, 2019
RecreationFitness CenterSports
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 (5,273 reviews)
$128/ night for 2 guests

excellent large old building, great location. Easy parking access, quick trip to Shedd/Field/etc.

Reviewed on Feb 12, 2019
RecreationPet FriendlyDining
Wyndham Grand Chicago Riverfront
Wyndham Grand Chicago Riverfront
4.0 out of 5.0 71 E Wacker Dr, Chicago
Free Cancellation
4.4/5 (7,268 reviews)
$97/ night for 2 guests

It located in the heart of Chicago, Illinois perfect walking distance from all the tourist attractions and from all the nice restaurants and bars. We asked the hotel for an upgrade because we were not completely satisfied with the room we had which was a city view. It was right at level of a terrace ...

Reviewed on Feb 11, 2019
RecreationConciergeFitness Center
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 (1,906 reviews)
$159/ night for 2 guests
RecreationFitness CenterSports
HI Chicago
HI Chicago
1.5 out of 5.0 24 East Congress Parkway, Chicago
Free Cancellation
4.3/5 (1,305 reviews)
$58/ night for 2 guests

great experience overall - friendly and helpful staff

Reviewed on Jan 8, 2019
RecreationWifiFree Wifi
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 (2,499 reviews)
$89/ night for 2 guests

The people working here are very friendly and helpful. I would stay there again

Reviewed on Jan 26, 2019
RecreationBreakfastFree Breakfast
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 (2,616 reviews)
$120/ night for 2 guests

great location comfortable room great lighting in the bathroom very comfortable bed

Reviewed on Feb 14, 2019
RecreationFitness CenterSports
Sheraton Grand Chicago
Sheraton Grand Chicago
4.0 out of 5.0 301 E North Water St, Chicago
Free Cancellation
4.2/5 (4,516 reviews)
$118/ night for 2 guests

Everything was super from the minute we stepped out of vehicle. The valet gentleman was courteous and informative, the room very clean, the housekeeping staff amazingly prompt, the complementary breakfast was fresh and the workout facility was one of the best we've seen in a hotel! We will definitely ...

Reviewed on Jan 7, 2019
RecreationConciergeBusiness
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 (3,365 reviews)
$67/ night for 2 guests

Location is great! But building is old, it only has one VERY small elevator, rooms are small and has old drafty windows in the bathrooms.

Reviewed on Feb 12, 2019
RecreationParkingFree Wifi
Club Quarters Hotel, Central Loop
Club Quarters Hotel, Central Loop
4.0 out of 5.0 111 West Adams Street, Chicago
Free Cancellation
4.3/5 (6,479 reviews)
$85/ night for 2 guests

The hotel is clean, sleek, modern, and very conveniently located in the Loop

Reviewed on Feb 12, 2019
RecreationBusinessDining
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 out of 5.0 10 S Wabash Ave, Chicago
Free Cancellation
4.6/5 (5,171 reviews)
$116/ night for 2 guests

Rooms were spacious and the bed was very comfortable.

Reviewed on Feb 14, 2019
RecreationBarDining
Kinzie Hotel
Kinzie Hotel
4.0 out of 5.0 20 W Kinzie St, Chicago
Free Cancellation
4.5/5 (4,337 reviews)
$93/ night for 2 guests

The staff at this hotel was extremely kind and helpful. We had a very quick check in and check out, nice breakfast, and very clean room. The room was spacious and updated, and we had a beautiful view! Would definitely go back and stay here again!

Reviewed on Feb 12, 2019
RecreationBreakfastBar
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4.0 out of 5.0 701 North Michigan Avenue, Chicago
Free Cancellation
4.1/5 (9,722 reviews)
$68/ night for 2 guests

Everything was perfect great location to the Mag Mike

Reviewed on Feb 3, 2019
RecreationConciergeDining
Chicago Athletic Association
Chicago Athletic Association
4.5 out of 5.0 12 South Michigan Avenue, Chicago
Free Cancellation
4.6/5 (1,433 reviews)
$118/ night for 2 guests

It was so unique, clean, had really great amenities. Also the cherry circle room was delicious. Would recommend highly!

Reviewed on Feb 11, 2019
RecreationDiningFree Wifi
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 (1,659 reviews)
$63/ night for 2 guests
RecreationDiningWifi
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Adventure Hotels: Our travelers loved these

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.