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

Hotels with Entertainment in Chicago

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Check availability on Chicago Hotels with Entertainment

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Chicago hotels with entertainment

A modern kitchen with a marble island, fruit bowls, and a city view.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.
A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.
A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.

1. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
United States
Ruby
S$328
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
A long dining table with chairs, overhead lighting, and a marble wall with a decorative ceiling.
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.
A grand lobby with ornate ceiling artwork, chandeliers, and a prominent 'P' emblem.
A modern building with large glass windows and a covered walkway.

2. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Downtown Chicago
United States
Sydney
S$327
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
The Intercontinental hotel facade with a large American flag and a floral display.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
A person sitting by a window with a cityscape view.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

3. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
United States
Kenan
S$367
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.
A cityscape with modern high-rise buildings, a river, and a boat.
A bar with a circular liquor display, seating with stools, and a city view through large windows.

4. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
United States
Mark
S$421
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
Front of property
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

5. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
United States
John
S$261
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.

6. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
United States
Poua
S$201
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A modern room with a view of a river and high-rise buildings.
A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.
A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

7. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Sharee
S$398
includes taxes & fees
1 Nov - 2 Nov
LondonHouse Chicago, Curio Collection by Hilton
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A conference room with a long table, chairs, and a vase.
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

8. River Hotel

River Hotel
Downtown Chicago
United States
Charlie
S$244
includes taxes & fees
25 Oct - 26 Oct
River Hotel
A high-rise hotel with a prominent Marriott sign, surrounded by other tall buildings and a busy street.
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.
A modern hotel room with a large window offering a city view, a kitchen area with a white countertop, and a seating area with a round coffee table.

9. Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
United States
jennifer
S$508
includes taxes & fees
23 Oct - 24 Oct
Chicago Marriott Downtown Magnificent Mile
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
A bar area with a marble countertop, bar stools, and a variety of bottles.
A spacious lobby with a marble floor, a reception desk, and a glass partition.
A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

10. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago
United States
Denys
S$280
includes taxes & fees
2 Nov - 3 Nov
Hotel Riu Plaza Chicago
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Top Chicago Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Wonderful experience. So close to the river walk and activities. Staff was so helpful and attentive and property was clean and comfy! Highly recommend!"
Susan 4-night trip
Posted 2 hours ago
River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"very helpful staff, large rest areas for waiting, good price, convenient location. A nice no-frills restaurant and bar onsite. Best choice for an Unpretentious visit stay."
Yang 4-night trip
Posted 2 hours ago
Club Quarters Hotel, Central Loop, Chicago
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Perfect location and clean rooms"
kelly 3-night trip
Posted 3 hours ago
The Royal Sonesta Chicago Downtown
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Old hotel! Front desk wasn’t helpful l, ask for several things and they never showed up. No A.C., coffee pot broken, ran out of toilet paper and towels. No ice in machine, vending machine served hot beverages. Maintenance men were very nice, Christian at the bar was excellent! I’ll never stay there again."
Pamela 4-night trip
Posted 3 hours ago
Congress Plaza Hotel
The Wade

The Wade

10/10 Excellent
"Real nice room facing the lake, comfy bed, nice decor, rain shower head, I prefer reg shower head, no Biggy ....one more thing, no coffee maker in the room but fresh coffee in the lobby."
joseph 1-night trip
Posted 3 hours ago
The Wade
Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Beautiful hotel in a great location!"
Mercy 3-night trip
Posted 3 hours ago
Hyatt Regency Chicago
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Friendly service; excellent location!"
Samuel 4-night trip
Posted 7 hours ago
L7 Chicago by LOTTE
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Great location, good sized rooms, comfortable beds"
Jake 2-night trip
Posted 8 hours ago
The Chicago Hotel Collection - Magnificent Mile
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Midland hotel was clean and tidy, and the staff were accommodating, friendly, and helpful throughout our stay. We had a pleasant experience and would definitely return in the future!"
Shiyabel 1-night trip
Posted 13 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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