Westchester Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Westchester hotels

Bar (on property)

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, (1,000 reviews)
"Good location for traveling around the area. Everything needed was on the property and Juan in particular in the restaurant and lounge was very engaging and attentive."
United States
Gerald Michael
The price is €106
includes taxes & fees
7 Jun - 8 Jun
Four Points by Sheraton Chicago Westchester/Oak Brook
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,508 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is €227
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,459 reviews)
"My favorite place to stay!"
United States
Teresa
The price is €214
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,240 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is €140
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,197 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is €177
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,237 reviews)
"Nice place to stay"
United States
Jimmie
The price is €163
includes taxes & fees
26 May - 27 May
Aloft by Marriott Chicago Mag Mile
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,171 reviews)
"The bar was very welcoming and the historic ambience and location was exceptional"
United States
Patricia
The price is €137
includes taxes & fees
25 May - 26 May
Congress Plaza Hotel
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,163 reviews)
"Great place"
United States
JOSE
The price is €236
includes taxes & fees
24 May - 25 May
Fairmont Chicago at Millennium Park
Lobby

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, (1,478 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is €151
includes taxes & fees
3 Jun - 4 Jun
The Chicago Hotel Collection Ambassador Gold Coast
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,556 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is €164
includes taxes & fees
25 May - 26 May
Eurostars Magnificent Mile
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,444 reviews)
"Great stay"
United States
Christa
The price is €124
includes taxes & fees
25 May - 26 May
The Chicago Hotel Collection - Magnificent Mile
2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,714 reviews)
"I had a great stay and would book again."
United States
Brandi
The price is €246
includes taxes & fees
25 May - 26 May
LondonHouse Chicago, Curio Collection by Hilton
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,802 reviews)
"Great staff and location. "
United States
Robert
The price is €229
includes taxes & fees
25 May - 26 May
Hilton Chicago
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,099 reviews)
"Very beautiful hotel!"
United States
Ingrid
The price is €193
includes taxes & fees
25 May - 26 May
Arlo Chicago
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (3,025 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is €106
includes taxes & fees
25 May - 26 May
Freehand Chicago
Lobby

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,010 reviews)
"All around great stay. "
United States
Nicholas
The price is €126
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Lobby

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,184 reviews)
"excellent stay"
United States
Jaeyoung
The price is €130
includes taxes & fees
25 May - 26 May
River Hotel
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,625 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is €276
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
Studio, 2 Double Beds | Bathroom

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,405 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is €211
includes taxes & fees
26 May - 27 May
Sports Illustrated Resorts Chicago
Exterior detail

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (616 reviews)
"Great stay!"
United States
Vanessa
The price is €136
includes taxes & fees
25 May - 26 May
FOUND Hotel Chicago River North
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.
View all properties
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
Schiller Woods view in Chicago of Illinois

Top Westchester Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"the room was clean, the staff was friendly! the rooftop bar was a bit expensive though."
Makayla 2-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile

More cheap stays in Westchester

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

22 West Algonquin Road Arlington Heights IL
The price is €55 per night from 4 Jun to 5 Jun
€55
4 Jun - 5 Jun
includes taxes & fees
5.4/10 (1,002 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 traveller data. Two other options for your stay in the area are River Hotel and Hotel Riu Plaza Chicago. See all available top hotels, or vacation rentals in Westchester.
What are some of the best holiday rentals that Westchester has to offer?
ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Westchester is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all 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?
Holiday Inn Chicago Dwtn - The Mart by IHG: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool and a sauna. Also, another option that features an on-site pool is Hilton Chicago. 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, Navy Pier and United Center. In Westchester, there are 17 hotels and other accommodation options to choose from. Find out more about Westchester.
What should I see while I'm in Westchester?
Wrigley Field, Navy Pier and United Center are some of the notable places to visit in the surrounding area. Additionally, you'll find Michigan Avenue 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