Westchester Hotels

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Check prices for these dates

Tonight
18 Feb - 19 Feb
Tomorrow
19 Feb - 20 Feb
This weekend
20 Feb - 22 Feb
Next weekend
27 Feb - 1 Mar

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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)
"The rooms were clean and the location was great. The staff made the stay amazing!"
United States
Patrice
The price is €107
includes taxes & fees
22 Feb - 23 Feb
Four Points by Sheraton Chicago Westchester/Oak Brook
Shared kitchen

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (461 reviews)
"Amazing staff and very clean, modern rooms!"
United States
genevieve
The price is €63
includes taxes & fees
1 Mar - 2 Mar
FOUND Hotel Chicago River North
Property amenity

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,682 reviews)
"Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. "
United States
Norah
The price is €88
includes taxes & fees
26 Feb - 27 Feb
The Wade
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,365 reviews)
"Amazing place, breakfast is great , location is great - honestly great hotel! "
United States
Brisa
The price is €122
includes taxes & fees
4 Mar - 5 Mar
Hotel Riu Plaza Chicago
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, (2,377 reviews)
"Great stay"
United States
Blake
The price is €159
includes taxes & fees
24 Feb - 25 Feb
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,301 reviews)
"Excellent stay, we loved it "
United States
Melani
The price is €171
includes taxes & fees
24 Feb - 25 Feb
Palmer House a Hilton Hotel
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, (1,282 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is €105
includes taxes & fees
19 Feb - 20 Feb
The Chicago Hotel Collection Ambassador Gold Coast
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,201 reviews)
"Place is always top notch..stay here anytime we stay in Chicago."
United States
Jon
The price is €150
includes taxes & fees
22 Feb - 23 Feb
Swissotel - Chicago
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,124 reviews)
"I always stay here when in town. "
United States
Jeffrey
Ivy Boutique Hotel
View from property

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful place to stay, nice staff 🙏"
United States
Yu Ching Dexter
The price is €155
includes taxes & fees
22 Feb - 23 Feb
The Blackstone, Autograph Collection
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,861 reviews)
"Absolutely enjoyed my time here"
United States
Quayshaun
The price is €84
includes taxes & fees
26 Feb - 27 Feb
Hilton Garden Inn Chicago Downtown South Loop
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1,211 reviews)
"Clean, great customer service, "
United States
Arturo
The Chicago Hotel Collection - Magnificent Mile
Interior

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2,764 reviews)
"I enjoyed my stay"
United States
Emily
The price is €72
includes taxes & fees
22 Feb - 23 Feb
Freehand Chicago
Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,060 reviews)
"Clean rooms, great staff, and great location."
United States
Romel
The price is €101
includes taxes & fees
22 Feb - 23 Feb
The Godfrey Hotel Chicago
Lounge

Pendry Chicago

Pendry Chicago
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,150 reviews)
"Excellent hotel and location."
United States
Marcelo
The price is €223
includes taxes & fees
15 Mar - 16 Mar
Pendry Chicago
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,807 reviews)
"Great stay"
United States
Jennifer
The price is €89
includes taxes & fees
24 Feb - 25 Feb
Hilton Chicago/Magnificent Mile Suites
55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3,672 reviews)
"Great location and overall great hotel."
United States
Fernando
The price is €160
includes taxes & fees
22 Feb - 23 Feb
L7 Chicago by LOTTE
Ice skating

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,231 reviews)
"Amazing hotel and staff!"
United States
Corey
Silversmith Hotel Chicago Downtown
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,009 reviews)
"Location was great, staff was very friendly, and the rooms were clean. "
United States
Lori
The price is €154
includes taxes & fees
4 Mar - 5 Mar
Staypineapple, An Iconic Hotel, The Loop
Restaurant

Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,383 reviews)
"Super comfy beds, helpful staff, free coffee and snacks and an amazing location "
United States
Stephanie
The price is €117
includes taxes & fees
27 Feb - 28 Feb
Hyatt Centric The Loop 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.
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Learn more about Westchester

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

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Top Westchester Hotel Reviews

More cheap stays in Westchester

Motel 6 Naperville, IL

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL
The price is €44 per night from 8 Mar to 9 Mar
€44
8 Mar - 9 Mar
includes taxes & fees
7.8/10 Good! (1,238 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 Hilton Chicago O'Hare Airport and Embassy Suites by Hilton Chicago Downtown River North. See all available top hotels, or vacation rentals in Westchester.
What are some of the best holiday rentals that Westchester has to offer?
A Home Away From Home!: This holiday home rental outside of Westchester offers a fireplace, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. 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?
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 Chicago and Aloft Chicago Mag Mile are two additional hotels with an on-site pool. 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 United Center, Wrigley Field and Michigan Avenue. In Westchester, there are 13 hotels and other accommodation options to choose from. Find out more about Westchester.
What should I see while I'm in Westchester?
United Center, Wrigley Field and Michigan Avenue are some of the notable places to visit in the surrounding area. Additionally, you'll find Soldier Field and Navy Pier 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.