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

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Check availability on Chicago Ski Hotels

This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Chicago ski hotels

A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.

1. The Peninsula Chicago

The Peninsula Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,006 reviews)
"Always an incredible hotel! Definitely one of the best in the USA"
United States
Vincent Haley
The price is ￥98,475
￥117,077 total
includes taxes & fees
Nov 22 - Nov 23
The Peninsula Chicago
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (2,073 reviews)
"Amazing property and hospitality!"
United States
Matthew
The price is ￥72,675
￥86,403 total
includes taxes & fees
Nov 15 - Nov 16
Trump International Hotel & Tower Chicago
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.

3. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (5,160 reviews)
"Amazing hotel will stay again"
United States
Matthew
The price is ￥20,550
￥24,433 total
includes taxes & fees
Nov 25 - Nov 26
L7 Chicago by LOTTE
A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.

4. Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
"Nice clean hotel in a great location."
United States
Tom
The price is ￥81,143
￥96,471 total
includes taxes & fees
Nov 22 - Nov 23
Park Hyatt Chicago
A rooftop terrace with a city skyline view, featuring a mix of modern and classic architecture, and several potted plants.

5. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
"The hotel lobby and rooftop are nice but the rooms are okay. We had 3 rooms and the shower pressure was terrible in all. The king room felt small so we switched to 2 queens which was much better. The service was so good though and it’s attached to a mall. It was good overall but probably won’t stay here again."
United States
Sabina
The price is ￥45,401
￥58,664 total
includes taxes & fees
Nov 23 - Nov 24
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

6. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,762 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is ￥20,625
￥29,953 total
includes taxes & fees
Nov 23 - Nov 24
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

7. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (5,636 reviews)
"All the stay was perfect, location is near to all the best places"
Mexico
JESUS VERA
The price is ￥24,677
￥33,830 total
includes taxes & fees
Nov 23 - Nov 24
Hotel Riu Plaza Chicago
A modern hotel with a curved glass facade, a prominent 'SOFITEL' sign, and a colorful entrance area.

8. Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,675 reviews)
"Great location - 2 blocks from Michigan avenue. Nice walkable neighborhood."
United States
Susan
The price is ￥34,506
￥45,709 total
includes taxes & fees
Nov 22 - Nov 23
Sofitel Chicago Magnificent Mile
A hotel room with a large bed, a wooden cabinet, a chair, and a view of the city skyline.

9. Viceroy Chicago

Viceroy Chicago
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,311 reviews)
"Beautiful hotel, friendly staff."
United States
Mary
The price is ￥38,482
￥50,967 total
includes taxes & fees
Nov 23 - Nov 24
Viceroy Chicago
A hotel entrance with a fountain, a car, and a person standing by the entrance.

10. Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Great hotel"
United States
Luis
The price is ￥78,957
￥93,880 total
includes taxes & fees
Nov 22 - Nov 23
Waldorf Astoria Chicago
A modern hotel room with a large bed, two armchairs, a small round table, and a view of a cityscape through floor-to-ceiling windows.

11. Loews Chicago Hotel

Loews Chicago Hotel
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,524 reviews)
"Excellent location and super friendly staff!"
United States
Rhiannon
The price is ￥32,999
￥44,868 total
includes taxes & fees
Nov 24 - Nov 25
Loews Chicago Hotel
A modern living room with a curved sofa, a glass coffee table, and a fireplace.

12. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (999 reviews)
"Great place to stay in Chicago!"
United States
ryan
The price is ￥78,780
￥93,662 total
includes taxes & fees
Nov 22 - Nov 23
Four Seasons Hotel Chicago
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

13. Hotel 505 River North

Hotel 505 River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (3,004 reviews)
"Great stay!"
United States
Miya
The price is ￥17,536
￥25,891 total
includes taxes & fees
Nov 22 - Nov 23
Hotel 505 River North
A hotel entrance with a marquee sign, outdoor seating, and a well-lit facade.

14. The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (194 reviews)
"Nice property overall Room was very nice Location excellent"
Canada
Michael
The price is ￥25,312
￥35,714 total
includes taxes & fees
Nov 23 - Nov 24
The Talbott, Autograph Collection
A modern indoor lounge area with seating, a coffee table, and potted plants.

15. Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,008 reviews)
"It was a great stay and the staff was super friendly"
United States
Sharon
The price is ￥30,724
￥42,048 total
includes taxes & fees
Nov 22 - Nov 23
Kimpton Gray Hotel by IHG
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

16. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,901 reviews)
"Excellent location"
Switzerland
Kevin
The price is ￥22,617
￥31,574 total
includes taxes & fees
Nov 23 - Nov 24
LondonHouse Chicago, Curio Collection by Hilton
A modern living room with a large TV, a sofa, a coffee table, and a chair. There is a large window with a city view.

17. Level Chicago - River North

Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,166 reviews)
"Very clean and convenient location."
United States
Veronica
The price is ￥21,691
￥29,358 total
includes taxes & fees
Nov 24 - Nov 25
Level Chicago - River North
A hotel room with a bed, a chair, a small table with flowers, and a large window with a city view.

18. Kinzie Hotel

Kinzie Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,169 reviews)
"Amazing hotel!"
United States
Alex
The price is ￥26,801
￥36,237 total
includes taxes & fees
Nov 23 - Nov 24
Kinzie Hotel
An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

19. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,003 reviews)
"Beautiful room, great breakfast and helpful staff"
United States
Peggy.
The price is ￥23,175
￥27,553 total
includes taxes & fees
Nov 25 - Nov 26
Hampton Inn Chicago West Loop Fulton Market Area
A modern kitchen with a large island, bar stools, and a city view.

20. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (557 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is ￥27,084
￥35,681 total
includes taxes & fees
Nov 23 - Nov 24
Level Chicago – Old Town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at ski hotels in Chicago

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4 stars

Top Chicago Hotel Reviews

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