Westchester Hotels from S$82

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
21 Jul - 22 Jul
Tomorrow
22 Jul - 23 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Westchester hotels

FOUND Hotel Chicago River North
Experience the vibrant atmosphere of this historic building, featuring ornate details and a lively dining and entertainment area.

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very good, (138)
"Great area and friendly staff...also check in was extremely easy!"
The price is S$185
includes taxes & fees
6 Aug - 7 Aug
FOUND Hotel Chicago River North
Ohio House Motel
Located at the corner of a bustling street, Ohio House features a flat roof and large glass windows.

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1009)
"Great place to stay!"
The price is S$169
includes taxes & fees
17 Aug - 18 Aug
Ohio House Motel
Holiday Inn Express Chicago - Magnificent Mile by IHG
Hotel facade with a balcony featuring a variety of flowers and large windows with metal railings.

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very good, (1009)
"Great stay"
The price is S$229
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Chicago - Magnificent Mile by IHG
Four Points by Sheraton Chicago Westchester/Oak Brook
Relax in comfort with plush seating and a long bar, surrounded by artwork and natural views.

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
8.4 out of 10, Very good, (1004)
"The hotel was wonderful!"
The price is S$142
includes taxes & fees
4 Aug - 5 Aug
Four Points by Sheraton Chicago Westchester/Oak Brook
Best Western Grant Park Hotel
Relax in a stylish seating area with plush armchairs and a decorative partition, surrounded by ambient lighting and a patterned rug.

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2563)
"Excellent Hotel!!"
The price is S$217
includes taxes & fees
14 Aug - 15 Aug
Best Western Grant Park Hotel
Travelodge by Wyndham Downtown Chicago
Relax in the hotel lobby's spacious seating area, surrounded by a city view and comfortable sofas and armchairs.

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2254)
"Best Travelodge I have stayed at "
The price is S$193
includes taxes & fees
18 Aug - 19 Aug
Travelodge by Wyndham Downtown Chicago
Freehand Chicago
Relax in style with plush seating and a classic design, featuring a sofa, armchairs, and a bookshelf.

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2090)
"Stayed many times, great fun!"
The price is S$220
includes taxes & fees
17 Aug - 18 Aug
Freehand Chicago
Crowne Plaza Chicago West Loop by IHG
Relax in a casual, urban setting with seating areas and a prominent counter for ordering.

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1294)
"Great location and hotel "
The price is S$247
includes taxes & fees
10 Aug - 11 Aug
Crowne Plaza Chicago West Loop by IHG
Level Chicago Fulton Market
Enjoy a modern dining experience with a long table, blue chairs, and a unique pendant light.

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (243)
"Great location, nice amenities"
Level Chicago Fulton Market
Congress Plaza Hotel
Experience grandeur in this beautifully designed ballroom with high ceilings, arched windows, and elegant table settings.

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8908)
"Great place to stay."
The price is S$268
includes taxes & fees
4 Aug - 5 Aug
Congress Plaza Hotel
Residence Inn Chicago Downtown Magnificent Mile
Located in a central urban area, this high-rise building offers a modern design with a glass facade.

Residence Inn Chicago Downtown Magnificent Mile

4.0 star property
9.6 out of 10, Exceptional, (304)
"This was a great hotel in a great location."
The price is S$294
includes taxes & fees
7 Aug - 8 Aug
Residence Inn Chicago Downtown Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago
Enjoy communal and dining experiences at this restaurant with a rustic charm, featuring a long counter, tables, and mounted TV.

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3345)
"Great location and nice rooms. "
The price is S$226
includes taxes & fees
27 Jul - 28 Jul
Club Quarters Hotel, Central Loop, Chicago
The Hoxton Chicago
Enjoy a casual dining experience with comfortable seating and a variety of beverages.

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1005)
"Excellent location and great vibe. "
The price is S$315
includes taxes & fees
17 Aug - 18 Aug
The Hoxton Chicago
The Chicago Hotel Collection River North
Enjoy a casual coffee break in our cozy coffee shop with a menu board, seating area, and unique decor.

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (525)
"The rooms were excellent"
The price is S$259
includes taxes & fees
23 Jul - 24 Jul
The Chicago Hotel Collection River North
Best Western River North Hotel
Relax on the rooftop with wicker lounge chairs and take in the city skyline views.

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1017)
"nice hotel and nice staff and close to everything "
The price is S$204
includes taxes & fees
17 Aug - 18 Aug
Best Western River North Hotel
Central Loop Hotel
Enjoy casual dining in a rustic setting with exposed brick walls and wooden furniture.

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1813)
"Nice room, great location and excellent staff."
The price is S$226
includes taxes & fees
27 Jul - 28 Jul
Central Loop Hotel
The Emily Hotel
Enjoy meals in a spacious dining area with sofas and chairs along a central aisle.

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1137)
"Great place"
The price is S$463
includes taxes & fees
21 Aug - 22 Aug
The Emily Hotel
Hilton Chicago
Classic hotel with a symmetrical facade and central entrance.

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2010)
"Great stay! "
The price is S$348
includes taxes & fees
9 Aug - 10 Aug
Hilton Chicago
Claridge House
Experience the hotel's elegant lobby, featuring a reception area, comfortable seating, and a unique rug with the hotel's logo.

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1257)
"Great breakfast options and welcoming vibe. Amazing location and overall great value."
The price is S$335
includes taxes & fees
23 Jul - 24 Jul
Claridge House
Millennium Knickerbocker Chicago
Experience the grandeur of our lobby, featuring a stunning chandelier, comfortable seating, and a beautiful staircase.

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1896)
"It was a wonderful stay"
The price is S$222
includes taxes & fees
13 Aug - 14 Aug
Millennium Knickerbocker Chicago
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
Sign in
Sign up, it's free

Learn more about Westchester

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

See all hotels in Westchester

Top Westchester Hotel Reviews

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Beautiful with excellent amenities "
Ervin 2-night trip
Posted 8 hours ago
Fairmont Chicago at Millennium Park

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 InterContinental Chicago Magnificent Mile by IHG 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'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?

InterContinental Chicago Magnificent Mile by IHG: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool and a steam room. Also, another option that features an on-site pool is Embassy Suites by Hilton Chicago Downtown River North. 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.