Westchester Hotels from S$101

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Check prices for these dates

Tonight
16 Feb - 17 Feb
Tomorrow
17 Feb - 18 Feb
Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar

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Top 10 trending Westchester hotels

Four Points by Sheraton Chicago Westchester/Oak Brook
Reception

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
8.4 out of 10, Very good, (1001)
"Friendly staff. Well cared for property."
The price is S$139
includes taxes & fees
23 Feb - 24 Feb
Four Points by Sheraton Chicago Westchester/Oak Brook
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2035)
"I recommend it 100 percent, very good service, clean, a beautiful view of the city"
The price is S$199
includes taxes & fees
24 Feb - 25 Feb
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Front of property – evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (1930)
"Great property. The location is great and the rooms are beautiful. A experience. "
The price is S$279
includes taxes & fees
17 Feb - 18 Feb
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1413)
"Hotel is extremely clean and the staff is very helpful "
The price is S$308
includes taxes & fees
17 Feb - 18 Feb
Loews Chicago Hotel
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2626)
"Excellent"
The price is S$197
includes taxes & fees
24 Feb - 25 Feb
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1812)
"Great property and well maintained"
The price is S$154
includes taxes & fees
18 Feb - 19 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1438)
"Great property."
The price is S$289
includes taxes & fees
23 Feb - 24 Feb
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Front of property – evening/night

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1629)
"Our family stayed three days for a birthday getaway. It was wonderful! We got a suite and two separate rooms for our adult children and their spouses and children. Throughout the hotel it was very elegant in all areas from doorman, lobby, spa, bar, restaurant and elevators. There were eight elevators so no waiting or being shoved in with multiple other people. Loved that! The rooms were beautifully laid out, clean and very well maintained. The suite room had a large dining area with bay windows...
The price is S$307
includes taxes & fees
21 Feb - 22 Feb
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Cocktail bar

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2606)
"I like the location, and the fact that it is close to restaurants/ grocery stores."
The price is S$119
includes taxes & fees
19 Feb - 20 Feb
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.6 out of 10, Excellent, (1006)
"nice i enjoyed my staycation "
The price is S$146
includes taxes & fees
17 Feb - 18 Feb
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.2 out of 10, Very good, (1639)
"The staff was nice and friendly. The hotel was clean and we had a beautiful view."
The price is S$180
includes taxes & fees
17 Feb - 18 Feb
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3200)
"Just a really nice hotel that I would choose when I go to Chicago"
The price is S$303
includes taxes & fees
17 Feb - 18 Feb
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2002)
"Love this hotel"
The price is S$194
includes taxes & fees
23 Feb - 24 Feb
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.4 out of 10, Very good, (1782)
"Beautiful hotel, clean, nice staff. Across the street from a parking garage which was convenient"
The price is S$142
includes taxes & fees
23 Feb - 24 Feb
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Lobby

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1034)
"Amazing view & great rooms "
The price is S$219
includes taxes & fees
23 Feb - 24 Feb
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Restaurant

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1006)
"My stay was great! I couldn’t believe the value for the money."
The price is S$165
includes taxes & fees
17 Feb - 18 Feb
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.0 out of 10, Very good, (1530)
"Great value "
The price is S$113
includes taxes & fees
24 Feb - 25 Feb
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (1452)
"The only thing I did not like were the hidden fees that you are not aware of until you are checking in."
The price is S$187
includes taxes & fees
24 Feb - 25 Feb
Hotel Riu Plaza Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2507)
"Great value for the location. "
The price is S$110
includes taxes & fees
27 Feb - 28 Feb
Best Western Grant Park Hotel
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8497)
"The last day of my stay, a guy with a huge balloon in the shape of a rat was making a lot of noise with a speaker at the main door of the hotel, something very unpleasant. I don't understand why the hotel allowed that."
The price is S$135
includes taxes & fees
17 Feb - 18 Feb
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

Romantic Westchester is calling! Discover its basketball, dining, golf and more.

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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 L7 Chicago by LOTTE and citizenM Chicago Downtown. 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's the best accommodation for a golf trip to Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a hotel featuring free WiFi and pillowtop beds, and it's a top choice for playing a round of golf. See more golf hotels in Westchester.

What are some accommodation options with pools in Westchester?

Hilton Chicago: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club. Hampton Inn Chicago-O'Hare International Airport and Aloft Chicago Mag Mile are two additional hotels with an on-site pool. 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, Michigan Avenue and Soldier Field. In Westchester, there are 5 hotels and other accommodation options to choose from. Find out more about Westchester.

What should I see while I'm in Westchester?

Wrigley Field, Michigan Avenue and Soldier Field are some of the notable places to visit in the surrounding area. Additionally, you'll find Navy Pier and United Center 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.