The Best Adventure Hotels in Chicago, IL from AED 469 in 2026 | Expedia

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

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Check availability on Chicago Adventure Hotels

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25 Oct - 26 Oct

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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 modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

A bar area with a long counter, multiple shelves of bottles, and four bar stools.

A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

1. L7 Chicago by LOTTE

Downtown Chicago

United States

Dimitri

AED 479

AED 569 total

includes taxes & fees

22 Nov - 23 Nov

A cityscape at dusk with illuminated skyscrapers and a river.

An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.

A modern bar area with a long counter, multiple bar stools, and a large flat-screen TV.

A spacious lobby with a central bar area, seating, and a large window offering a city view.

2. Holiday Inn Chicago Dwtn - The Mart by IHG

Downtown Chicago

United States

Pamela

AED 481

AED 681 total

includes taxes & fees

23 Nov - 24 Nov

A grand lobby with a central bar, high ceilings, and classical architecture.

A grand hallway with ornate ceiling, chandeliers, and a reception desk at the end.

A spacious lobby with a grand chandelier, a fireplace, and elegant seating arrangements.

A modern living room with a sofa set, ottoman, and armchairs.

3. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

United States

Carrie

AED 437

AED 520 total

includes taxes & fees

22 Nov - 23 Nov

A modern lounge with a curved glass wall offering a city view, plush seating, and ambient lighting.

A spacious indoor area with a high ceiling, a dining area with tables and chairs, and a seating area with sofas and armchairs.

A modern lobby with a large mirror, bookshelves, seating areas, and a reception desk.

A modern interior with wooden shelves, a fireplace, and a round mirror.

4. Thompson Chicago, by Hyatt

Downtown Chicago

Canada

Kyle

AED 558

AED 772 total

includes taxes & fees

23 Nov - 24 Nov

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 rooftop pool area with lounge chairs and umbrellas, a city skyline view, and a no diving sign.

A building facade with a dark entrance, two wall-mounted lights, and a sign reading "The Robey Chicago".

A modern interior with a bar area, seating, and large windows offering a city view.

5. 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

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.

6. Chicago Marriott Downtown Magnificent Mile

Downtown Chicago

United States

Monica

AED 676

AED 935 total

includes taxes & fees

23 Nov - 24 Nov

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A residential street with a sidewalk, houses, and greenery.

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.

7. Carleton of Oak Park

Oak Park

United States

Kim

AED 450

AED 499 total

includes taxes & fees

28 Oct - 29 Oct

A high-rise building with a modern glass facade and a historic building with a green roof in the background.

A woman descending a set of outdoor stairs in an urban area with tall buildings in the background.

A person seated by a window with a city view, a small table with bottles and glasses, and a pair of glasses on the table.

A modern bar area with a long counter, multiple bar stools, and a large flat-screen TV.

8. voco Chicago Downtown - Riverwalk by IHG

Downtown Chicago

United States

Tyrrell

AED 477

AED 677 total

includes taxes & fees

23 Nov - 24 Nov

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Top Chicago Hotel Reviews

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent

"Great spot!"

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"We will certainly return! A lovely mix of character and a feel of fancy! Really cool and unique rooms!"

Hilton Chicago

Hilton Chicago

10/10 Excellent

"I absolutely love this property!"

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"Very close to everything."

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Safe for solo travelers. Good vibes, great"

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent

"Great location, spacious room, great city and rêver views, window bench seat was perfect for people watching"

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent

"Beautiful place and easy access to downtown"

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Very nice affordable place to stay !!!"

Freehand Chicago

Freehand Chicago

8/10 Good

"Good value"

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