Westchester Hotels from S$80

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Our top choices for Westchester hotels

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, (1,000 reviews)
"The room has clean & quiet. Nothing special. Did not try the breakfast. Decent stay. Nothing special. "
United States
GARY
The price is S$157
includes taxes & fees
7 Jun - 8 Jun
Four Points by Sheraton Chicago Westchester/Oak Brook

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,493 reviews)
"Great place to stay "
United States
Mark
The price is S$327
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,830 reviews)
"We enjoy our stay."
United States
Nuria
The price is S$256
includes taxes & fees
25 May - 26 May
The Wade

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,622 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is S$371
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,323 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is S$356
includes taxes & fees
26 May - 27 May
Swissotel - Chicago

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,466 reviews)
"The staff was extremely polite, and the hotel was in the most convenient area for the activities we were doing. Great visit!"
United States
Keira
The price is S$249
includes taxes & fees
25 May - 26 May
DoubleTree by Hilton Chicago - Magnificent Mile

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, (2,846 reviews)
"It is a clean room and breakfast and the drinks and it was so nice in the inside the hotel"
United States
Sparkle
The price is S$266
includes taxes & fees
25 May - 26 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,153 reviews)
"Great place"
United States
JOSE
The price is S$336
includes taxes & fees
26 May - 27 May
Fairmont Chicago at Millennium Park

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,226 reviews)
"Nice place to stay"
United States
Jimmie
The price is S$225
includes taxes & fees
27 May - 28 May
Aloft Chicago Mag Mile

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,253 reviews)
"Great stay! "
United States
Taira
The price is S$187
includes taxes & fees
25 May - 26 May
Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,446 reviews)
"Great place to stay."
United States
Yuge
The price is S$226
includes taxes & fees
25 May - 26 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,000 reviews)
"The breakfast was great."
United States
Liangsheng
The price is S$214
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,294 reviews)
"Beautiful Hotel great location"
United States
Nereida
The price is S$226
includes taxes & fees
25 May - 26 May
Hilton Chicago/Magnificent Mile Suites

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,969 reviews)
"Loved everything including location and food options. Great hotel. "
United States
Eileen
The price is S$244
includes taxes & fees
25 May - 26 May
Millennium Hotel Knickerbocker Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,514 reviews)
"Clean room , nice staff, nice view"
United States
John Hok-Lam
The price is S$408
includes taxes & fees
25 May - 26 May
Hyatt Regency Chicago

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,092 reviews)
"Great stay!"
United States
Milo
The price is S$293
includes taxes & fees
25 May - 26 May
Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,896 reviews)
"A wonderful stay"
United States
Lateia
The price is S$245
includes taxes & fees
25 May - 26 May
Courtyard by Marriott Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,409 reviews)
"great place "
United States
Jasar
The price is S$184
includes taxes & fees
25 May - 26 May
The Chicago Hotel Collection - Magnificent Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,143 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is S$262
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,116 reviews)
"Great location, safe, clean and reasonable price. "
United States
Anthony
The price is S$202
includes taxes & fees
26 May - 27 May
Congress Plaza Hotel
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

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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 traveller data. Two other options for your stay in the area are River Hotel and Hotel Riu Plaza Chicago. 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! Most hotel room reservations are refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before check in. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Westchester.
What is the favourite LGBTQ-friendly accommodation in Westchester?
Four Points by Sheraton Chicago Westchester/Oak Brook is a top LGBTQ-friendly hotel, and features free Wi-Fi and pillowtop beds. See all available hotels listed as LGBTQ-friendly in Westchester.
What's the best dog-friendly place to stay in Westchester?
Four Points by Sheraton Chicago Westchester/Oak Brook is a top hotel for people travelling with their pets, and offers a restaurant and a fitness centre for its human guests. See more pet-friendly hotel accommodations in Westchester.
What are some accommodation options with pools in Westchester?
Holiday Inn Chicago Dwtn - The Mart by IHG: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool and a sauna. Also, another option that features an on-site pool is Hilton Chicago. View all hotels with pools in Westchester.
What's it like to stay in Westchester?
Visitors to Westchester will definitely 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 accommodation options 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. Take a look at what more there is to see and do in Expedia's Westchester guide.
What's the seasonal weather in Westchester?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Westchester are January, November, February and December, with each month seeing an average of 13 cm of snowfall.

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