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Our top choices for Westchester 5-star hotels

Terrace/patio

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,946 reviews)
"Great stay and location."
United States
Tammy Lynn
The price is SAR 1,760
SAR 2,092 total
includes taxes & fees
9 Aug - 10 Aug
Trump International Hotel & Tower Chicago
Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (999 reviews)
"Liked the layout of our suite and that the hotel was right inside the shopping Mall & Bloomingdales."
United States
August
The price is SAR 1,971
SAR 2,343 total
includes taxes & fees
9 Aug - 10 Aug
Four Seasons Hotel Chicago
Lobby

The Langham, Chicago

The Langham, Chicago
5.0 star property
Downtown Chicago
9.8 out of 10, Exceptional, (1,005 reviews)
"Lux accommodations, great spa!"
United States
Gregory
The price is SAR 1,960
SAR 2,330 total
includes taxes & fees
9 Aug - 10 Aug
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, (1,004 reviews)
"Welcoming and attentive staff throughout the hotel made my stay an enjoyable and memorable experience."
United States
Charles
The price is SAR 2,440
SAR 2,901 total
includes taxes & fees
9 Aug - 10 Aug
The Peninsula Chicago
Exterior

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,000 reviews)
"Beautiful property with great location in Chicago. Can’t wait to stay again."
United States
Steve
The price is SAR 2,010
SAR 2,390 total
includes taxes & fees
9 Aug - 10 Aug
Waldorf Astoria Chicago
Cafe

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
5.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,000 reviews)
"I have stayed at this hotel a few times and each time it is better than the last. Great service, great location. Can’t wait to come back again."
United States
Caryn
The price is SAR 2,147
SAR 2,553 total
includes taxes & fees
21 Aug - 22 Aug
The Ritz-Carlton, Chicago
Indoor pool, open 6:00 AM to 9:00 PM, sun loungers

Nobu Hotel Chicago

Nobu Hotel Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (889 reviews)
"Beautiful room and property"
United States
Girlynda
The price is SAR 1,641
SAR 1,951 total
includes taxes & fees
26 Jul - 27 Jul
Nobu Hotel Chicago
Breakfast, lunch, dinner and brunch served

Park Hyatt Chicago

Park Hyatt Chicago
5.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,000 reviews)
"Our room was wonderful"
United States
Jennifer
The price is SAR 2,078
SAR 2,470 total
includes taxes & fees
9 Aug - 10 Aug
Park Hyatt Chicago
2 restaurants; breakfast, lunch, dinner, and brunch served

The St. Regis Chicago

The St. Regis Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (127 reviews)
"We had a great stay and will come back again in the near future!"
United States
Princess
The price is SAR 2,316
SAR 2,754 total
includes taxes & fees
16 Aug - 17 Aug
The St. Regis Chicago
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2 reviews)
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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
The price is SAR 828 per night from Aug 21 to Aug 22
SAR 828
SAR 972 total
21 Aug - 22 Aug
includes taxes & fees
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PoolSpaHot tubBreakfast includedWaterpark
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A calm lake with ducks, autumn trees, and a grassy park area.

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Westchester?
The amount you pay for a 5-star hotel in Westchester depends on things like when you plan to go and the length of your escape. Our top tip for scoring an awesome deal? Use our pricing filters to compare all of the available hotels for your preferred dates.

  • Search for the lowest price per night from SAR 809

What makes a hotel 5 stars in Westchester?
Flawless guest service is the defining feature of every 5-star hotel in Westchester. From the instant you arrive, staff attend to your every need, whether recommending activities and tours or providing in-room massage treatments. Plus, hotels must feature upscale conveniences to be considered for a 5-star rating. These can include luxury toiletries, a wellness center, swimming pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Westchester?
Use Expedia's filter tool to find a luxurious escape in Westchester where everything you need is included. After your initial search, narrow down your results for properties that have 5 stars and are deemed "All inclusive." The main thing on the itinerary at these stays? Pure enjoyment and indulgence.

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