Westchester Hotels from S$75

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Westchester hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2104)
"Great place to stay!"
The price is S$320
includes taxes & fees
1 Sept - 2 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1338)
"Great stay highly recommend!! "
The price is S$525
includes taxes & fees
29 Aug - 30 Aug
Claridge House

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2250)
"Great stay "
The price is S$176
includes taxes & fees
2 Sept - 3 Sept
Freehand Chicago

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
8.4 out of 10, Very good, (1006)
"Hotel room was nice and clean!"
The price is S$131
includes taxes & fees
3 Sept - 4 Sept
Four Points by Sheraton Chicago Westchester/Oak Brook

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1964)
"Great room and close to attractions "
Silversmith Hotel Chicago Downtown

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very good, (1091)
"Great place to stay, would definitely recommend and stay here again "
The price is S$193
includes taxes & fees
1 Sept - 2 Sept
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (574)
"It was a wonderful place to stay! "
The price is S$192
includes taxes & fees
1 Sept - 2 Sept
The Chicago Hotel Collection River North

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2018)
"Overall a nice place to stay."
The price is S$216
includes taxes & fees
3 Sept - 4 Sept
DoubleTree by Hilton Chicago - Magnificent Mile

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very good, (1019)
"Great hotel! "
The price is S$210
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Express Chicago - Magnificent Mile by IHG

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1008)
"Great place to stay!"
The price is S$166
includes taxes & fees
2 Sept - 3 Sept
Ohio House Motel

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1010)
"Great location and hotel "
The price is S$218
includes taxes & fees
3 Sept - 4 Sept
Ivy Boutique Hotel

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1701)
"Had a great stay! The area is very walkable and convenient!!"
Hotel Saint Clair- Magnificent Mile

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4.0 star property
9.6 out of 10, Exceptional, (1025)
"Great stay, highly recommended"
The price is S$264
includes taxes & fees
22 Sept - 23 Sept
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1202)
"Great location, nice room and roomy bathroom and good breakfast."
The Chicago Hotel Collection - Magnificent Mile

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3363)
"Great location, quiet rooms "
The price is S$195
includes taxes & fees
2 Sept - 3 Sept
Club Quarters Hotel, Central Loop, Chicago

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2099)
"Great spot, good location, nice rooms. "
Hotel Felix River North/Magnificent Mile

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1905)
"Nice property "
The price is S$270
includes taxes & fees
1 Sept - 2 Sept
The Godfrey Hotel Chicago

Kinzie Hotel

4.0 star property
9.2 out of 10, Wonderful, (1863)
"Our room was comfortable, the staff was excellent, the breakfast was as expected and the happy hour was a nice touch. "
The price is S$306
includes taxes & fees
1 Sept - 2 Sept
Kinzie Hotel

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1962)
"Great stay"
The price is S$235
includes taxes & fees
2 Sept - 3 Sept
Millennium Knickerbocker Chicago

Residence Inn Chicago Downtown Magnificent Mile

4.0 star property
9.6 out of 10, Exceptional, (332)
"Great experience and great hotel "
The price is S$300
includes taxes & fees
3 Sept - 4 Sept
Residence Inn 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.
Save an average of 15% on thousands of hotels when you're signed in

Hotels near Westchester Attractions

Top Westchester Hotel Reviews

More cheap stays in Westchester

More cheap stays in Westchester

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Palmer House a Hilton Hotel and Hilton Garden Inn Chicago Downtown/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! 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?

Palmer House a Hilton Hotel: Hotel steps from State Street. Offers a full-service spa, an indoor pool and a 24-hour fitness centre. Hilton Garden Inn Chicago Downtown/Magnificent Mile and Embassy Suites by Hilton Chicago Downtown River North 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 8 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.