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Westchester 5 Stars Hotels

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Check availability on Westchester 5 Star Hotels

Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Westchester 5-star hotels

A person sitting by a window with a view of a cityscape, including a tall tower.
A group of people on a boat with a city skyline in the background.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.
A couple walking through a spacious lobby with marble flooring, large white floral arrangements, and a modern staircase in the background.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Teresa
NT$19,529
NT$23,218 total
includes taxes & fees
Oct 4 - Oct 5
Four Seasons Hotel Chicago
A cityscape with a river, a bridge, and a dining area with tables and chairs.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.
A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.
A modern hotel room with large windows, white furniture, and a view of tall buildings.

2. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
Downtown Chicago
United States
Jorge
NT$16,552
NT$19,679 total
includes taxes & fees
Oct 4 - Oct 5
Trump International Hotel & Tower Chicago
A modern hotel lobby with a reception desk, seating area, and large windows offering city views.
A modern hotel room with a large window offering a city view, three armchairs arranged around a central coffee table, and a decorative hanging plant.
A spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.
A swimming pool with a ceiling of lights, large windows, and potted plants.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
NT$21,435
NT$25,484 total
includes taxes & fees
Oct 4 - Oct 5
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A rooftop bar with seating and a view of the city skyline at night.
A modern bar area with a checkered floor, bar stools, and a bartender.
A spacious hotel lobby with multiple seating areas, a grand staircase, and large windows offering views of the city.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Levi
NT$21,435
NT$25,484 total
includes taxes & fees
Sep 29 - Sep 30
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.
An indoor swimming pool with a modern design, a reception area with a sign for Waldorf Astoria Chicago, and a seating area with two people.
A bar area with a long counter, multiple stools, and a seating area with a booth.
A bar area with a polished marble floor, bar stools, a counter with bottles, and a decorative lamp.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
NT$20,919
NT$24,870 total
includes taxes & fees
Oct 25 - Oct 26
Waldorf Astoria Chicago
A modern indoor swimming pool with a clear blue water surface, a wooden ceiling, and a wall with a floral pattern.
A modern hotel room with a large window, a wooden desk, a bathroom with a mirror, and a view of the cityscape.
A modern lobby with a sofa, a coffee table, and a vase of flowers.
A rooftop terrace with a view of a city skyline at dusk.

6. Nobu Hotel Chicago

Nobu Hotel Chicago
Downtown Chicago
United States
Abhay
NT$14,550
NT$18,093 total
includes taxes & fees
Oct 4 - Oct 5
Nobu Hotel Chicago
A couple dining at a table with a view of a cityscape and a sunset.
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.
A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.
A rooftop terrace with a dining table, chairs, and a view of the cityscape, including the Water Tower Place building.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
NT$20,434
NT$24,294 total
includes taxes & fees
Oct 27 - Oct 28
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
A modern lobby with a central seating area, large windows, and a decorative ceiling feature.
A rooftop lounge with outdoor seating, a fire pit, and a large reflective sculpture.
A modern bar area with a central bar, multiple seating options, and a large chandelier.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Fred
NT$15,878
NT$18,877 total
includes taxes & fees
Oct 25 - Oct 26
The Ritz-Carlton, Chicago
A restaurant with tables and chairs arranged in a corridor, large windows, and hanging lamps.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.
A modern hotel lobby with a large seating area, a view of the city, and a green accent wall.
A dining area with wicker chairs and tables, overlooking a marina with boats and a Ferris wheel.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
NT$21,022
NT$24,993 total
includes taxes & fees
Oct 25 - Oct 26
The St. Regis Chicago
A rooftop lounge with a city skyline view, featuring a sofa set with patterned cushions and a table with drinks and snacks.
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with bar stools.
A spacious lounge area with multiple seating options, including sofas and chairs, and a bar area with shelves of bottles and glasses.
A coastal city skyline with modern high-rise buildings, a beach, and a clear blue sky.

10. Art Villa

Art Villa
West Town
Art Villa
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River Hotel

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NT$5,906
NT$7,022 total
Oct 25 - Oct 26
includes taxes & fees
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The Chicago Hotel Collection Ambassador Gold Coast

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NT$5,683
NT$6,757 total
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THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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172 W Adams St Chicago IL
NT$6,319
NT$7,513 total
Oct 23 - Oct 24
includes taxes & fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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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?
You can find several pricing options for a 5-star hotel in Westchester on Expedia. The amount you pay will depend on your vacation dates, trip length and other factors. Compare all of the available accommodations for your chosen dates and make use of our pricing and other filters to land the perfect upscale stay.
  • Search for the lowest price per night from NT$6,757
What makes a hotel 5 stars in Westchester?
From high-end dining venues and all-day fitness centers to pools and luxury bedding, the 5-star experience in Westchester is all about comfort and luxury. But it takes more than just top-notch amenities to receive a 5-star rating. Hotels also have to provide remarkable guest-centric services like in-room massage treatments, dry cleaning and laundry and 24/7 room service.
Are there any 5-star all-inclusive resorts in Westchester?
Find an indulgent escape that includes your room, meals, drinks and entertainment in Westchester with Expedia's filters. Search for hotels with a 5-star rating and click on the "All inclusive" filter. Be sure to check what's included in the upfront price. This way, you're ready to take advantage of the premium perks on offer when you arrive.

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