Westchester Hotels from S$76

Start date: Check-in selected.
To Date
End date: Check-out
    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
Star rating

Top 10 trending Westchester hotels

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
8.4 out of 10, Very good, (1012)
"Great hotel, very clean and family staff"
The price is S$130
includes taxes & fees
6 Oct - 7 Oct
Four Points by Sheraton Chicago Westchester/Oak Brook

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3080)
"Perfect location, walkable to many restaurants and shops"
The price is S$284
includes taxes & fees
29 Oct - 30 Oct
Eurostars Magnificent Mile

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2863)
"Had a great stay!"
The price is S$244
includes taxes & fees
5 Oct - 6 Oct
Aloft Chicago Mag Mile

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4721)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is S$294
includes taxes & fees
5 Oct - 6 Oct
River Hotel

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (4014)
"Excellent central location and local dining options. "
The price is S$292
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2404)
"Location was excellent would stay there again"
The price is S$189
includes taxes & fees
28 Oct - 29 Oct
Freehand Chicago

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1042)
"It was a great stay"
The price is S$231
includes taxes & fees
2 Oct - 3 Oct
Best Western River North Hotel

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9349)
"The staff was top notch, the bed so comfortable, just a great overall stay"
Congress Plaza Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2087)
"Great location and very nice staff!!"
The price is S$278
includes taxes & fees
19 Oct - 20 Oct
DoubleTree by Hilton Chicago - Magnificent Mile

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (260)
"Lovely hotel."
The price is S$153
includes taxes & fees
1 Oct - 2 Oct
FOUND Hotel Chicago River North

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2225)
"Very nice hotel "
The price is S$317
includes taxes & fees
23 Oct - 24 Oct
Hilton Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2179)
"Great hotel "
The price is S$327
includes taxes & fees
19 Oct - 20 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2500)
"Nice hotel with amazing breakfasts and location."
The price is S$294
includes taxes & fees
29 Oct - 30 Oct
Hotel Riu Plaza Chicago

citizenM Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (3891)
"Absolutely loved this hotel and location. "
The price is S$330
includes taxes & fees
30 Oct - 31 Oct
citizenM Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2568)
"Good place to stay"
The price is S$309
includes taxes & fees
2 Oct - 3 Oct
La Quinta Inn & Suites by Wyndham Chicago Downtown

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3011)
"Enjoyed our stay"
The price is S$244
includes taxes & fees
20 Oct - 21 Oct
Hilton Chicago/Magnificent Mile Suites

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1555)
"Excellent breakfast and room was quiet and clean. "
The price is S$244
includes taxes & fees
2 Oct - 3 Oct
Crowne Plaza Chicago West Loop by IHG

The Allegro Royal Sonesta Hotel Chicago Loop

4.0 star property
9.0 out of 10, Wonderful, (2084)
"Great place to stay, close to everything!"
The price is S$349
includes taxes & fees
5 Oct - 6 Oct
The Allegro Royal Sonesta Hotel Chicago Loop

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2390)
"The rooms were quiet, clean, and the bed was comfortable."
The price is S$178
includes taxes & fees
20 Oct - 21 Oct
Travelodge by Wyndham Downtown Chicago

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1995)
"Excellent hotel, staff, location. "
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.
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

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 Hilton Chicago/Magnificent Mile Suites 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?

Hilton Garden Inn Chicago Downtown/Magnificent Mile: Hotel, 4-minute walk from Michigan Avenue. Provides complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions. Also, another option that features an on-site pool is InterContinental Chicago Magnificent Mile by IHG. 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 10 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia