Compare and book 5 Star hotels in Westchester, Chicago

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Check availability on Westchester 5 Star Hotels

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Westchester 5 Star Hotels

Reception
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (999)
"Amazing hotel"
United States
David
The price is 11.208.525 ₫
13.157.687 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Four Seasons Hotel Chicago
Lobby
The Langham, Chicago

The Langham, Chicago

5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1000)
"Langham is always a superior stay"
United States
THADDEUS LAMONT
The price is 12.733.237 ₫
14.947.546 ₫ total
includes taxes & fees
28 Dec - 29 Dec
The Langham, Chicago
Front of property – evening/night
The Peninsula Chicago

The Peninsula Chicago

5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1000)
"Excellent service throughout the hotel"
United States
Karen
The price is 12.526.225 ₫
14.704.536 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Peninsula Chicago
Bar (on property)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1784)
"Great stay "
United States
Mohammed
The price is 7.291.581 ₫
8.559.587 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Trump International Hotel & Tower Chicago
Exterior
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1002)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is 10.442.916 ₫
12.258.939 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Waldorf Astoria Chicago
Suite, Terrace (Water Tower) | Premium bedding, down duvets, pillow-top beds, minibar
Park Hyatt Chicago

Park Hyatt Chicago

5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1000)
"Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!! "
United States
Larissa
The price is 11.471.385 ₫
13.466.257 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
Park Hyatt Chicago
Indoor pool, open 6:00 AM to 9:00 PM, pool loungers
Nobu Hotel Chicago

Nobu Hotel Chicago

5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (754)
"Great location, amenities and staff. "
United States
Nicholas
The price is 8.122.268 ₫
9.534.729 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Nobu Hotel Chicago
Bar (on property)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1002)
"Great breakfast a la carte menu, perfect bar setting, room was spotless, and service in accordance to the Ritz Brand."
United States
Alejandro Randolph
The price is 9.770.456 ₫
11.469.538 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
The Ritz-Carlton, Chicago
2 restaurants, breakfast served
The St. Regis Chicago

The St. Regis Chicago

5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (83)
"Nice place "
United States
John
The price is 11.761.466 ₫
13.806.785 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The St. Regis Chicago
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Westchester.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL
The price is 2.486.974 ₫ per night from 18 Dec to 19 Dec
2.486.974 ₫
2.919.459 ₫ total
18 Dec - 19 Dec
includes taxes & fees
8.4/10 Very Good! (5,331 reviews)
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Schiller Woods view in Chicago of Illinois

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Westchester?
How much you pay for a 5-star hotel in Westchester can vary according to what time of year you travel and how long you plan to be away, among several factors. Take advantage of our price per night filter and other search tools to find the best rate on an indulgent stay.

  • Search for the lowest price per night from 2.919.459 ₫

What makes a hotel 5 stars in Westchester?
In Westchester, a hotel must offer a certain level of upscale conveniences to be designated 5 stars. These can include gourmet restaurants, saunas and spas, on-site gyms, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You'll enjoy things like nightly turn-down services, concierge services and in-room massages. Some may even offer extra touches like a welcome gift.
Are there any 5-star all-inclusive resorts in Westchester?
Use our convenient filters to find an upmarket retreat in Westchester where most of what you need is included. After your initial search, narrow your results for hotels that have a rating of 5 stars and are categorised as "All inclusive." The main thing on the to-do list at these stays? Relaxation and indulgence.

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