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May 29 - May 31
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Jun 5 - Jun 7

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Our top choices for Westchester hotels

Bar (on property)

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook
3.0 star property
Westchester
8.6 out of 10, Excellent, (1,004 reviews)
"Central location for my trip"
United States
James
The price is ₩157,969
₩176,895 total
includes taxes & fees
Jun 29 - Jun 30
Four Points by Sheraton Chicago Westchester/Oak Brook
Lobby

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
4.0 star property
Rosemont
8.8 out of 10, Excellent, (2,590 reviews)
"The breakfast is always exceptional. "
United States
Kimberly
The price is ₩239,211
₩272,652 total
includes taxes & fees
Jun 28 - Jun 29
Hyatt Regency O'Hare Chicago
Exterior

Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport
3.0 star property
Rosemont
8.4 out of 10, Very Good, (3,398 reviews)
"Great place to stay"
United States
abhishek
The price is ₩231,489
₩263,853 total
includes taxes & fees
Jun 28 - Jun 29
Hyatt Place Chicago/O'Hare Airport
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (1,517 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is ₩235,164
₩279,576 total
includes taxes & fees
Jun 22 - Jun 23
The Chicago Hotel Collection Ambassador Gold Coast
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (3,033 reviews)
"Great location nice room"
United States
Nolan
The price is ₩219,653
₩288,001 total
includes taxes & fees
Jun 29 - Jun 30
Freehand Chicago
Restaurant

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,490 reviews)
"Great location and super nice hotel"
United States
Karolina
The price is ₩391,313
₩509,961 total
includes taxes & fees
Jun 29 - Jun 30
Sofitel Chicago Magnificent Mile
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,016 reviews)
"Clean quiet hotel"
United States
Daniel
The price is ₩284,359
₩338,079 total
includes taxes & fees
Jun 29 - Jun 30
Hilton Garden Inn Chicago Downtown South Loop
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,288 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is ₩284,357
₩380,950 total
includes taxes & fees
Jun 30 - Jul 1
Hotel Riu Plaza Chicago
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,648 reviews)
"Great fitness room Nice lobby with bar and restaurants on site"
United States
Andrew
The price is ₩391,313
₩518,896 total
includes taxes & fees
Jun 30 - Jul 1
Sheraton Grand Chicago Riverwalk
Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,492 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is ₩317,185
₩377,102 total
includes taxes & fees
Jun 30 - Jul 1
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (1,005 reviews)
"Great hotel"
United States
Aysa
The price is ₩488,368
₩580,621 total
includes taxes & fees
Jun 14 - Jun 15
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,033 reviews)
"Clean room, friendly staff, nearby lots of stores and restaurants. "
United States
Nadiah
The price is ₩240,715
₩330,343 total
includes taxes & fees
Jun 29 - Jun 30
Warwick Allerton - Chicago
Exterior

Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,326 reviews)
"Great hotel , the location is was great so close to everything we had planned"
United States
Daniel
The price is ₩353,955
₩420,817 total
includes taxes & fees
Jun 28 - Jun 29
Hyatt Place Chicago/Downtown - The Loop
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,077 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is ₩334,689
₩442,208 total
includes taxes & fees
Jun 28 - Jun 29
Staypineapple, An Iconic Hotel, The Loop
Lobby lounge

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,000 reviews)
"Would definitely stay here again! Clean, friendly staff, great location."
United States
Heather
The price is ₩297,203
₩379,988 total
includes taxes & fees
Jun 29 - Jun 30
Le Méridien Essex Chicago
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,791 reviews)
"Very clean room, nice breakfast and really nice hotel restaurant"
United States
Hugo
The price is ₩334,540
₩424,029 total
includes taxes & fees
Jun 28 - Jun 29
La Quinta Inn & Suites by Wyndham Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,244 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is ₩240,542
₩331,895 total
includes taxes & fees
Jun 28 - Jun 29
Silversmith Hotel Chicago Downtown
Bar (on property)

Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,489 reviews)
"Absolutely fabulous! Would stay again"
United States
Cortney
The price is ₩335,555
₩398,942 total
includes taxes & fees
Jun 28 - Jun 29
Canopy by Hilton Chicago Central Loop
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,115 reviews)
"Very beautiful hotel!"
United States
Ingrid
The price is ₩329,840
₩437,635 total
includes taxes & fees
Jun 29 - Jun 30
Arlo Chicago
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very Good, (2,852 reviews)
"Breakfast was excellent."
United States
Janine
The price is ₩328,789
₩434,730 total
includes taxes & fees
Jun 28 - Jun 29
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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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Learn more about Westchester

Upscale Westchester is calling! Discover its basketball, food, golf, and more.

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Schiller Woods view in Chicago of Illinois

Top Westchester Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Great view"
Maria 4-night trip
Posted less than an hour ago
Hilton Chicago

More cheap stays in Westchester

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

22 West Algonquin Road Arlington Heights IL
The price is ₩92,731 per night from Jun 20 to Jun 21
₩92,731
₩103,841 total
Jun 20 - Jun 21
includes taxes & fees
5.4/10 (1,003 reviews)

Frequently asked questions

What's the best place to stay in Westchester?
Located 13.3 mi (21.4 km) from the heart of Westchester, Congress Plaza Hotel is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Hotel Riu Plaza Chicago and The Chicago Hotel Collection - Magnificent Mile. See all available top hotels, or vacation rentals in Westchester.
If I need to cancel my hotel reservation in Westchester, will I receive a refund?
Yes! The majority of hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Westchester.
Where can I learn more about changing or cancelling my trip to Westchester?
To access more information about updating your trip to Westchester or cancelling it, click here.
What is the top LGBTQ-friendly place to stay in Westchester?
Four Points by Sheraton Chicago Westchester/Oak Brook is a top LGBTQ-friendly hotel, and features free WiFi and pillowtop beds. See all available hotels listed as LGBTQ-friendly in Westchester.
What's the best pet-friendly accommodation in Westchester?
Four Points by Sheraton Chicago Westchester/Oak Brook is a top hotel for people traveling with their pets, and offers a restaurant and a fitness center for its human guests. See more pet-friendly hotel accommodations in Westchester.
What are some accommodations with pools in Westchester?
Holiday Inn Chicago Dwtn - The Mart by IHG: Hotel, 3-minute walk from Merchandise Mart. Offers 2 restaurants, an indoor pool, and a sauna. Aloft by Marriott Chicago Mag Mile and Hilton Chicago/Magnificent Mile Suites are two additional hotels that feature an onsite pool. View all hotels with pools in Westchester.
What's the best accommodation near O'Hare International Airport (ORD)?
Hilton Chicago O'Hare Airport is a popular 4-star hotel featuring 2 restaurants and 2 bars. It's located a short 0.1 mi (0.1 km) from O'Hare Intl. Airport. Other good options close to the airport are Edward Hotel Chicago and Best Western At O'Hare.
How is it to stay in Westchester?
Visitors to Westchester are sure to enjoy the shopping and restaurants. Tourists can also enjoy so much more including its basketball games. Around the area, top sights include Wrigley Field, Navy Pier, and United Center. In Westchester, there are 17 hotels and other accommodations to choose from. Find out more about Westchester.
What should I see while I'm in Westchester?
Wrigley Field, Navy Pier, and United Center are some of the notable places to visit in the surrounding area. Additionally, you'll find Michigan Avenue and Soldier Field in the area. Check out what more to see and do in Expedia's Westchester guide.
What's the seasonal weather like in Westchester?
The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.