A river with a yellow boat, surrounded by tall buildings and a bridge.

Find Adventure Hotels in Chicago, IL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chicago Adventure Hotels

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chicago adventure hotels

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.

1. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
United States
Amanda
AED 474
AED 564 total
includes taxes & fees
23 Nov - 24 Nov
L7 Chicago by LOTTE
A high-rise hotel with a prominent Marriott sign, surrounded by other tall buildings and a busy street.
A modern gym with treadmills, weight machines, and a curved ceiling.
A hotel room with a large bed, a desk, a chair, and a TV. There are large windows with curtains, and a city view.
A modern bar area with a central island, bar stools, and a television screen displaying a news program.

2. Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
United States
jennifer
AED 676
AED 935 total
includes taxes & fees
23 Nov - 24 Nov
Chicago Marriott Downtown Magnificent Mile
A street view with a row of buildings, including a store with a large glass window and a bus stop.
A modern living room with a dining area, large windows, and a unique ceiling light fixture.
A kitchen with a microwave, coffee makers, and a shelf with glassware and dishes.
A hallway with a bench, a door, and a wall-mounted light fixture.

3. City Suites Hotel

City Suites Hotel
Lakeview
United States
Vincentius
AED 426
AED 500 total
includes taxes & fees
17 Nov - 18 Nov
City Suites Hotel
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A hotel room with two beds, a desk, a chair, a large window with a view, and a modern wall design.

4. The Wade

The Wade
Downtown Chicago
United States
Ashaleigh
AED 437
AED 520 total
includes taxes & fees
23 Nov - 24 Nov
The Wade
A breakfast setting with a plate of toast, a bowl of fruit, a cup of coffee, and a newspaper on a table by a window with a city view.
A bar area with a circular bar, stools, and a well-stocked shelf of bottles.
A modern interior with a bar area, seating, and large windows offering a city view.
A building facade with a dark entrance, two wall-mounted lights, and a sign reading "The Robey Chicago".

5. The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels
West Town
United States
Patricia
AED 624
AED 824 total
includes taxes & fees
23 Nov - 24 Nov
The Robey, Chicago, a Member of Design Hotels
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
A residential street with a sidewalk, houses, and greenery.

6. Carleton of Oak Park

Carleton of Oak Park
Oak Park
United States
Brad
AED 450
AED 499 total
includes taxes & fees
4 Nov - 5 Nov
Carleton of Oak Park
A cityscape at dusk with illuminated skyscrapers and a river.
A spacious lobby with a high ceiling, modern seating, and a central bar area.
A spacious lobby with a central bar area, seating, and a large window offering a city view.
A modern bar area with a long counter, multiple bar stools, and a large flat-screen TV.

7. Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
Downtown Chicago
United States
Pamela
AED 511
AED 716 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Chicago Dwtn - The Mart by IHG
Room
Meeting facility
A vending machine and a refrigerated display case stocked with snacks and beverages in a commercial setting.
A hotel room with a large bed, a bedside table, a bench, a wall-mounted lamp, and a window with curtains.

8. Best Western At O'Hare

Best Western At O'Hare
Rosemont
United States
Wendy
AED 340
AED 388 total
includes taxes & fees
1 Nov - 2 Nov
Best Western At O'Hare
A hotel room with a bed, a desk, a television, and a window with a view of buildings.
A well-appointed lounge area with a fireplace, leather armchairs, and a checkered floor.
A lobby with a reception desk, a green counter, a bar area, and a seating area with leather chairs.
The Willows Hotel with a classical facade, arched windows, and a signboard.

9. The Willows Hotel

The Willows Hotel
Lakeview
United States
daniel
AED 381
AED 448 total
includes taxes & fees
23 Nov - 24 Nov
The Willows Hotel
A hotel with a prominent 'HOTEL FELIX' sign, surrounded by tall buildings and a tree-lined street.
A person pouring a drink into a glass with ice and an orange slice garnish.
A modern interior with a round table, four chairs, a vase with flowers, and a view of the street through large windows.
A hotel room with two beds, a dining table with chairs, a city view, and a minibar.

10. Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
Downtown Chicago
United States
William
AED 370
AED 562 total
includes taxes & fees
22 Nov - 23 Nov
Hotel Felix River North/Magnificent Mile
View all properties

Top Chicago Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great location very clean and impressive room. Bedrooms have 3 stairs so for people with mobility issue they should reserve the room where it says accessible. We did not have problems. Great stay."
Dennis 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile
Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Lovely hotel in a great location, I stayed on the 23rd floor, the room was brilliant but the windows did not shield the sound of sirens all night!"
Stephen 5-night trip
Posted 7 hours ago
Eurostars Magnificent Mile
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Great location, right in downtown Chicago. Close to everything. Close to all the train stations"
Susana 2-night trip
Posted 16 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Lovely bar and Champagne room. For our first couple of nights the rooftop was inviting with firepit and sofas. Gorgeous! Last night, it had been almost emptied! Staff was so friendly but not very informative about the area. Room is very basic. No coffee maker in room. The soaps and shampoos very minimal. A grand hotel that seems a little tired! I believe room makeovers are scheduled!"
Susan 2-night trip
Posted 18 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Historic hotel that has some upgrades and modern amenities. The lobby bar could use some upgrades and a second working elevator on the South tower would have been helpful on busy days."
Marc 2-night trip
Posted 20 hours ago
Congress Plaza Hotel

Explore a world of travel with Expedia