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Find 5 Star Hotels in Westchester, IL from ￥30,010

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Check availability on Westchester 5 Star Hotels

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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.
A modern bar area with a central bar and multiple stools, surrounded by a high ceiling with a decorative light fixture.
An indoor swimming pool with a skylight, a lifeguard chair, and a potted plant.

1. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Downtown Chicago
United States
Teresa
￥97,631
￥116,074 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 modern hotel room with large floor-to-ceiling windows offering a city view.
A pool area with a view of a cityscape, a lounge with wicker furniture, and a person relaxing in the pool.
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
￥82,748
￥98,379 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 spacious lobby with a modern sofa, armchairs, and a coffee table. A large window offers a view of the cityscape.
A modern dining area with round tables, comfortable chairs, and a dessert display.
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.

3. The Langham, Chicago

The Langham, Chicago
Downtown Chicago
United States
Saramae
￥96,679
￥114,941 total
includes taxes & fees
Oct 25 - Oct 26
The Langham, Chicago
A high-rise hotel with multiple floors, large windows, and a prominent Tiffany & Co. store on the ground level.
A spacious hotel lobby with multiple seating areas, a grand staircase, and large windows offering views of the city.
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.

4. The Peninsula Chicago

The Peninsula Chicago
Downtown Chicago
United States
Levi
￥107,156
￥127,398 total
includes taxes & fees
Oct 4 - Oct 5
The Peninsula Chicago
A black luxury car parked in front of a hotel entrance with a glass canopy decorated with festive ornaments.
A couple dining on a balcony with a cityscape view.
A bar area with a long counter, multiple stools, and a seating area with a booth.
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.

5. Waldorf Astoria Chicago

Waldorf Astoria Chicago
Downtown Chicago
United States
Luis
￥111,323
￥132,353 total
includes taxes & fees
Oct 26 - Oct 27
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
￥68,730
￥85,681 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 woman sitting by a window with a city view, holding a cup and saucer.
A modern hotel room with a large bed, a seating area, a TV, and a view of the city and ocean.
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.

7. Park Hyatt Chicago

Park Hyatt Chicago
Downtown Chicago
United States
Tom
￥107,157
￥127,398 total
includes taxes & fees
Oct 18 - Oct 19
Park Hyatt Chicago
A modern indoor space with a glass ceiling, marble flooring, and contemporary furniture.
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.
A spacious lobby with a central seating area, a reception desk, and a large chandelier.

8. The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago
Downtown Chicago
United States
Fred
￥79,375
￥94,370 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 lobby with a large seating area, a view of the city, and a green accent wall.
A rooftop pool area with city views, two lounge chairs, and a small table with a vase.
A modern hotel entrance with a prominent "STREGIS" sign, large glass windows, and a well-lit facade.

9. The St. Regis Chicago

The St. Regis Chicago
Downtown Chicago
United States
Xiomara
￥105,093
￥124,944 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 living room with a fireplace, a mounted TV displaying Netflix content, and a staircase leading to another level.
A spacious lounge area with multiple seating options, including sofas and chairs, and a bar area with shelves of bottles and glasses.

10. Art Villa

Art Villa
West Town
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.
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
￥26,009
￥30,923 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (5,440 reviews)
River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
￥25,554
￥30,381 total
Oct 25 - Oct 26
includes taxes & fees
8/10 Very Good! (2,338 reviews)
The Chicago Hotel Collection Ambassador Gold Coast
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL
￥25,241
￥30,010 total
Sep 27 - Sep 28
includes taxes & fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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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 ￥30,010
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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