Westchester Hotels from S$59

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13 Nov - 14 Nov
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14 Nov - 15 Nov
This weekend
14 Nov - 16 Nov
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21 Nov - 23 Nov

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Top 10 trending Westchester hotels

Breakfast and dinner served
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, (1002)
"Had an excellent experience staying here"
United States
James
The price is S$127
includes taxes & fees
2 Dec - 3 Dec
Four Points by Sheraton Chicago Westchester/Oak Brook
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3090)
"Awesome location and excellent service, the staff was great!"
United States
Salvador
The price is S$165
includes taxes & fees
14 Dec - 15 Dec
Eurostars Magnificent Mile
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2896)
"Had a wonderful stay! The hotel was very comfortable, clean, and relaxing. The staff were friendly and helpful, and the room was cozy and well-maintained. Would definitely stay here again!"
United States
Angel
The price is S$151
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile
Reception
River Hotel

River Hotel

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4794)
"Beautiful hotel. Had a nice stay"
United States
Esther
The price is S$151
includes taxes & fees
26 Nov - 27 Nov
River Hotel
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (4157)
"Friendly staff, very comfortable room"
United States
Randall
The price is S$131
includes taxes & fees
25 Nov - 26 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Outdoor pool, 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, (2138)
"Very nice hotel "
United States
Patrick
The price is S$149
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2569)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is S$145
includes taxes & fees
7 Dec - 8 Dec
Freehand Chicago
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
Downtown Chicago
8.2 out of 10, Very good, (319)
"very clean and modern, staff was very friendly"
United States
Edrick
The price is S$103
includes taxes & fees
7 Dec - 8 Dec
FOUND Hotel Chicago River North
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2294)
"Great staff. Great room."
United States
Monica
The price is S$200
includes taxes & fees
24 Nov - 25 Nov
Hilton Chicago
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (9568)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is S$227
includes taxes & fees
15 Nov - 16 Nov
Congress Plaza Hotel
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2772)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is S$195
includes taxes & fees
8 Dec - 9 Dec
Hotel Riu Plaza Chicago
Terrace/patio
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, (2225)
"Room was spotless…staff was great!"
United States
Tamika
The price is S$196
includes taxes & fees
24 Nov - 25 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1676)
"We really enjoyed our stay, and the balcony view was beautiful."
United States
Marnecia
The price is S$138
includes taxes & fees
23 Nov - 24 Nov
Crowne Plaza Chicago West Loop by IHG
Terrace/patio
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4034)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is S$174
includes taxes & fees
20 Nov - 21 Nov
citizenM Chicago Downtown
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1002)
"Really great location and warm and friendly staff"
United Kingdom
David
The price is S$168
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Chicago - Downtown by IHG
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3281)
"Comfortable stay , great location."
United States
Carlos A.
The price is S$149
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
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, (2604)
"Enjoyed my stay here. "
United States
Vai
The price is S$173
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Chicago Downtown
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3346)
"Great stay!"
United States
Shanell
The price is S$177
includes taxes & fees
26 Nov - 27 Nov
voco Chicago Downtown - Riverwalk by IHG
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2058)
"Great place to stay."
United States
Aaron
The price is S$194
includes taxes & fees
23 Nov - 24 Nov
Palmer House a Hilton Hotel
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2063)
"Beautiful hotel, great location, helpful staff, and an exceptional price!"
United States
McAndrew
Silversmith Hotel Chicago Downtown
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.

See all hotels in Westchester
Schiller Woods view in Chicago of Illinois

Top Westchester Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"We loved our stay!! The views in the panoramic room were amazing!! Rooms were clean. Definitely coming back!! "
Italo 2-night trip
Posted 2 days ago
Eurostars Magnificent Mile

More cheap stays in Westchester

Motel 6 Naperville, IL

Motel 6 Naperville, IL

1585 Naperville Wheaton Road, Naperville, IL
The price is S$72 per night from 7 Dec to 8 Dec
S$72
7 Dec - 8 Dec
includes taxes & fees
7.8/10 Good! (1,111 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, Embassy Suites by Hilton Chicago Downtown River North is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Congress Plaza Hotel and Hilton Chicago/Magnificent Mile Suites. 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?
Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool and flat-screen televisions. Hilton Garden Inn Chicago Downtown/Magnificent Mile 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 Navy Pier. In Westchester, there are 11 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 Navy Pier are some of the notable places to visit in the surrounding area. Additionally, you'll find United Center 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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