Westchester Hotels

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

Next weekend
In two weeks

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
8.6 out of 10, Excellent, (1002)
"Clean room, friendly staff"
The price is P5,266
P5,897 total
includes taxes & fees
Nov 3 - Nov 4
Four Points by Sheraton Chicago Westchester/Oak Brook

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3058)
"Perfect location, walkable to many restaurants and shops"
The price is P6,366
P7,473 total
includes taxes & fees
Nov 3 - Nov 4
Eurostars Magnificent Mile

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2844)
"Had a great stay!"
The price is P8,507
P9,986 total
includes taxes & fees
Nov 2 - Nov 3
Aloft Chicago Mag Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (4026)
"We definitely will stay there again place was very nice "
The price is P10,365
P12,167 total
includes taxes & fees
Oct 19 - Oct 20
Hilton Garden Inn Chicago Downtown/Magnificent Mile

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4710)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is P12,674
P14,877 total
includes taxes & fees
Oct 6 - Oct 7
River Hotel

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2416)
"Great walkable location to all the sights! "
The price is P5,521
P7,500 total
includes taxes & fees
Nov 4 - Nov 5
Freehand Chicago

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9300)
"Beautiful hotel!"
The price is P7,383
P8,667 total
includes taxes & fees
Nov 2 - Nov 3
Congress Plaza Hotel

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1018)
"Great stay"
The price is P7,329
P8,604 total
includes taxes & fees
Nov 2 - Nov 3
Best Western River North Hotel

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2077)
"Great hotel"
The price is P9,213
P10,815 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Chicago - Magnificent Mile

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very Good, (263)
"Loved this place if you want something affordable and nice! "
The price is P5,641
P6,621 total
includes taxes & fees
Nov 4 - Nov 5
FOUND Hotel Chicago River North

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2240)
"Very nice hotel "
The price is P10,643
P14,193 total
includes taxes & fees
Oct 23 - Oct 24
Hilton Chicago

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2166)
"Great hotel "
The price is P11,065
P14,667 total
includes taxes & fees
Nov 2 - Nov 3
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2533)
"Location is great and the breakfast buffet is amazing"
The price is P9,284
P12,529 total
includes taxes & fees
Nov 3 - Nov 4
Hotel Riu Plaza Chicago

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3903)
"Great place to stay. "
The price is P10,034
P11,779 total
includes taxes & fees
Nov 4 - Nov 5
citizenM Chicago Downtown

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (3018)
"Enjoyed our stay"
The price is P8,359
P9,813 total
includes taxes & fees
Nov 3 - Nov 4
Hilton Chicago/Magnificent Mile Suites

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2563)
"Good place to stay"
The price is P9,181
P11,797 total
includes taxes & fees
Nov 2 - Nov 3
La Quinta Inn & Suites by Wyndham Chicago Downtown

The Allegro Royal Sonesta Hotel Chicago Loop

4.0 star property
9.0 out of 10, Wonderful, (2096)
"We had an amazing stay for a weekend getaway. "
The price is P14,410
P18,767 total
includes taxes & fees
Oct 6 - Oct 7
The Allegro Royal Sonesta Hotel Chicago Loop

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2383)
"Comfortable bed, bright room, good shower, very accessible location."
The price is P6,247
P7,334 total
includes taxes & fees
Nov 4 - Nov 5
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

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
8.8 out of 10, Excellent, (3176)
"Great stay "
The price is P12,326
P14,469 total
includes taxes & fees
Oct 19 - Oct 20
voco Chicago Downtown - Riverwalk by IHG
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

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 traveler data. Other good options for your trip to the area are Freehand Chicago and Embassy Suites by Hilton Chicago Downtown River North. 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?

Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool, and flat-screen televisions. Hilton Garden Inn Chicago Downtown/Magnificent Mile and InterContinental Chicago Magnificent Mile by IHG 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 11 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia