Westchester Hotels from S$66

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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, (1,001 reviews)
"The rooms were clean and the location was great. The staff made the stay amazing!"
United States
Patrice
The price is S$153
includes taxes & fees
22 Feb - 23 Feb
Four Points by Sheraton Chicago Westchester/Oak Brook

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (449 reviews)
"Amazing staff and very clean, modern rooms!"
United States
genevieve
The price is S$80
includes taxes & fees
22 Feb - 23 Feb
FOUND Hotel Chicago River North

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,065 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is S$126
includes taxes & fees
22 Feb - 23 Feb
Aloft Chicago Mag Mile

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,376 reviews)
"Super comfy beds, helpful staff, free coffee and snacks and an amazing location "
United States
Stephanie
The price is S$142
includes taxes & fees
27 Feb - 28 Feb
Hyatt Centric The Loop Chicago

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,666 reviews)
"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "
United States
Norah
The price is S$132
includes taxes & fees
22 Feb - 23 Feb
The Wade

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,085 reviews)
"Great place"
United States
Nicholas
The price is S$137
includes taxes & fees
15 Feb - 16 Feb
Club Quarters Hotel Wacker at Michigan, Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,789 reviews)
"Great stay"
United States
Jennifer
The price is S$133
includes taxes & fees
18 Feb - 19 Feb
Hilton Chicago/Magnificent Mile Suites

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,757 reviews)
"i've stayed here twice now and its so incredibly charming and beautiful, staff is friendly, and very affordable, HIGHLY reccomend!!"
United States
Jayden
The price is S$102
includes taxes & fees
16 Feb - 17 Feb
Freehand Chicago

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,526 reviews)
"Great location, friendly staff and nice room"
United States
Srinivasa
The price is S$121
includes taxes & fees
22 Feb - 23 Feb
Claridge House Chicago, Tapestry Collection by Hilton

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,040 reviews)
"Great place"
United States
Omar
The price is S$157
includes taxes & fees
16 Feb - 17 Feb
Warwick Allerton - Chicago

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,000 reviews)
"Great place to stay..awesome staff!"
United States
Veronica
The price is S$127
includes taxes & fees
8 Mar - 9 Mar
Le Méridien Essex Chicago

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, (1,283 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is S$157
includes taxes & fees
15 Feb - 16 Feb
The Chicago Hotel Collection Ambassador Gold Coast

Best Western River North Hotel

Best Western River North Hotel
2.5 star property
Downtown Chicago
7.8 out of 10, Good, (1,047 reviews)
"Kind staff, simple rooms but clean. Will stay again."
United States
Lauren
The price is S$111
includes taxes & fees
15 Feb - 16 Feb
Best Western River North Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,304 reviews)
"Great staff, room spotless, great price."
United States
Robert
The price is S$136
includes taxes & fees
18 Feb - 19 Feb
DoubleTree by Hilton Chicago - Magnificent Mile

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,049 reviews)
"Clean rooms, great staff, and great location."
United States
Romel
The price is S$146
includes taxes & fees
22 Feb - 23 Feb
The Godfrey Hotel Chicago

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4,998 reviews)
"Great stay, good location, accommodating staff."
United States
Ian
The price is S$137
includes taxes & fees
15 Feb - 16 Feb
River Hotel

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,290 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is S$231
includes taxes & fees
21 Feb - 22 Feb
Palmer House a Hilton Hotel

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4,357 reviews)
"All things about this hotel was good from the location to the staff"
United States
Cisco
The price is S$120
includes taxes & fees
18 Feb - 19 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very good, (3,941 reviews)
"Great location, the room was nice and the breakfast was good. Overall great value for this property"
United States
Jorge
The price is S$105
includes taxes & fees
16 Feb - 17 Feb
The Whitehall Hotel, BW Premier Collection

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,554 reviews)
"I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic."
United States
Equilla
Hotel Felix River North/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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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 DoubleTree by Hilton Chicago - Magnificent Mile and Embassy Suites by Hilton Chicago Downtown River North. 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?
DoubleTree by Hilton Chicago - Magnificent Mile: Hotel, 5-minute walk from Michigan Avenue. Offers a rooftop terrace, a seasonal outdoor pool and LED televisions. Embassy Suites by Hilton Chicago Downtown River North and Hilton Chicago 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 13 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 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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