Westchester Hotels

    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, (1002)
"Hotel room was nice and clean!"
The price is P5,415
P6,063 total
includes taxes & fees
Sep 1 - Sep 2
Four Points by Sheraton Chicago Westchester/Oak Brook

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3081)
"Great location and wonderful views of the city we enjoyed our stay! "
The price is P8,219
P9,648 total
includes taxes & fees
Aug 25 - Aug 26
Eurostars Magnificent Mile

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4545)
"Great place to stay, staff was very friendly"
The price is P6,879
P8,076 total
includes taxes & fees
Sep 1 - Sep 2
River Hotel

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (3731)
"Our stay was wonderful."
The price is P8,669
P10,177 total
includes taxes & fees
Aug 26 - Aug 27
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2807)
"Clean, helpful staff and in walking distance to most places we visited."
The price is P7,922
P9,300 total
includes taxes & fees
Sep 1 - Sep 2
Aloft Chicago Mag Mile

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1031)
"Great location "
The price is P7,219
P8,474 total
includes taxes & fees
Sep 1 - Sep 2
Best Western River North Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2003)
"Pool area and deck were great for the family, beds were comfortable, location is great."
The price is P9,074
P10,652 total
includes taxes & fees
Aug 26 - Aug 27
DoubleTree by Hilton Chicago - Magnificent Mile

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2221)
"Great stay "
The price is P6,002
P8,049 total
includes taxes & fees
Sep 2 - Sep 3
Freehand Chicago

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8994)
"lovely hotel, room was clean with comfy bed and great facilities. would definitely stay here again "
The price is P10,721
P12,585 total
includes taxes & fees
Sep 14 - Sep 15
Congress Plaza Hotel

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very Good, (191)
"Great place "
The price is P5,555
P6,521 total
includes taxes & fees
Sep 2 - Sep 3
FOUND Hotel Chicago River North

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very Good, (1015)
"Friendly staff and close to the places I wanted to go to "
The price is P8,663
P10,854 total
includes taxes & fees
Sep 4 - Sep 5
Holiday Inn & Suites Chicago - Downtown by IHG

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2097)
"Awesome hotel, highly recommended."
The price is P7,975
P11,035 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2087)
"Great place to stay!"
The price is P9,301
P12,571 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2488)
"Had a wonderful stay here and staff was super friendly!"
The price is P7,643
P9,975 total
includes taxes & fees
Sep 1 - Sep 2
La Quinta Inn & Suites by Wyndham Chicago Downtown

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very Good, (1873)
"Helpful staff, beautiful hotel in a great location!"
The price is P9,883
P13,027 total
includes taxes & fees
Sep 2 - Sep 3
Palmer House a Hilton Hotel

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2314)
"Beautiful hotel , breakfast was amazing "
The price is P8,602
P11,705 total
includes taxes & fees
Sep 2 - Sep 3
Hotel Riu Plaza Chicago

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3602)
"Great place"
The price is P8,199
P9,624 total
includes taxes & fees
Aug 24 - Aug 25
citizenM Chicago Downtown

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1011)
"Great stay"
The price is P8,219
P9,648 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Chicago - Magnificent Mile by IHG

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very Good, (2056)
"Great stay "
The price is P7,615
P8,939 total
includes taxes & fees
Sep 3 - Sep 4
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1952)
"Perfect stay! Great 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

Near an Attraction

Learn more about Westchester

Romantic Westchester is calling! Discover its basketball, food, golf, and more.

Top Westchester Hotel 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, Congress Plaza Hotel is a top choice for your stay based on our traveler data. Other good options for your trip to 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! The majority of hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Westchester.

Where can I learn more about changing or cancelling my trip to Westchester?

To access more information about updating your trip to Westchester or cancelling it, click here.

What is the top LGBTQ-friendly place to stay in Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a top LGBTQ-friendly hotel, and features free WiFi and pillowtop beds. See all available hotels listed as LGBTQ-friendly in Westchester.

What's the best pet-friendly accommodation in Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a top hotel for people traveling with their pets, and offers a restaurant and a fitness center for its human guests. See more pet-friendly hotel accommodations in Westchester.

What are some accommodations 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 center. Hilton Garden Inn Chicago Downtown/Magnificent Mile and Embassy Suites by Hilton Chicago Downtown River North are two additional hotels that feature an onsite pool. View all hotels with pools in Westchester.

What's the best accommodation near O'Hare International Airport (ORD)?

Hilton Chicago O'Hare Airport is a popular 4-star hotel featuring 2 restaurants and 2 bars. It's located a short 0.1 mi (0.1 km) from O'Hare Intl. Airport. Other good options close to the airport are Edward Hotel Chicago and Best Western At O'Hare.

How is it to stay in Westchester?

Visitors to Westchester are sure to 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 accommodations 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. Check out what more to see and do in Expedia's Westchester guide.

What's the seasonal weather like in Westchester?

The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.