Westchester Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

Our top choices for Westchester hotels

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, (1,001 reviews)
"The rooms were clean and the location was great. The staff made the stay amazing!"
United States
Patrice
The price is €110
includes taxes & fees
3 May - 4 May
Four Points by Sheraton Chicago Westchester/Oak Brook

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,362 reviews)
"Fantastic location and a luxury hotel for a fair price."
United States
Cornelius
The price is €226
includes taxes & fees
9 Apr - 10 Apr
Sofitel Chicago Magnificent Mile

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, (2,437 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is €210
includes taxes & fees
6 Apr - 7 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,399 reviews)
"Loved this hotel!"
United States
Ellen
The price is €130
includes taxes & fees
12 Apr - 13 Apr
DoubleTree by Hilton Chicago - Magnificent Mile

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,724 reviews)
"Great hotel "
United States
Marina
The price is €156
includes taxes & fees
28 Apr - 29 Apr
Hotel Riu Plaza Chicago

Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,228 reviews)
"This location was fantastic! Right in the middle of everything we wanted to see in Chicago. "
United States
Ashlee
The price is €164
includes taxes & fees
26 Apr - 27 Apr
Hyatt Place Chicago/Downtown - The Loop

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,162 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is €123
includes taxes & fees
12 Apr - 13 Apr
Aloft Chicago Mag Mile

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,742 reviews)
"Clean room, nice staff, good breakfast. "
United States
America.
The price is €143
includes taxes & fees
12 Apr - 13 Apr
La Quinta Inn & Suites by Wyndham Chicago Downtown

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, (1,944 reviews)
"Hotel was really nice"
United States
LaCarr
The price is €128
includes taxes & fees
27 Apr - 28 Apr
Hilton Garden Inn Chicago Downtown South Loop

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, (1,353 reviews)
"Very beautiful place to stay"
United States
angie
The price is €113
includes taxes & fees
21 Apr - 22 Apr
The Chicago Hotel Collection Ambassador Gold Coast

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,080 reviews)
"Clean room, very new, excellent stay"
United States
Anthony
The price is €180
includes taxes & fees
12 Apr - 13 Apr
Hyatt Centric Chicago Magnificent Mile

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,243 reviews)
"Excellent stay."
United States
Fenton
The price is €250
includes taxes & fees
10 Apr - 11 Apr
Swissotel - Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,894 reviews)
"Overall a great stay."
United States
Joshua
The price is €225
includes taxes & fees
6 Apr - 7 Apr
Radisson Blu Aqua Hotel Chicago

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,008 reviews)
"Clean room and great staff"
United States
Lon
The price is €181
includes taxes & fees
12 Apr - 13 Apr
Hampton Inn Chicago West Loop Fulton Market Area

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,804 reviews)
"Every thing was in walking distance and the hotel is beautiful I will definitely be back "
United States
Shannon
The price is €139
includes taxes & fees
12 Apr - 13 Apr
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,300 reviews)
"Nice hotel and great location "
United States
Chelsey
The price is €150
includes taxes & fees
30 Apr - 1 May
Homewood Suites by Hilton Chicago Downtown South Loop

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,416 reviews)
"My family and I had a very good two night stay. I would stay here again."
United States
Juliette
The price is €131
includes taxes & fees
12 Apr - 13 Apr
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

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, (1,003 reviews)
"Great stay "
United States
Jennifer
The price is €109
includes taxes & fees
12 Apr - 13 Apr
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,158 reviews)
"Great stafff great breakfast great location "
United States
Nancy
The price is €125
includes taxes & fees
12 Apr - 13 Apr
Homewood Suites by Hilton Chicago-Downtown

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,005 reviews)
"Great views close to museums and great restaurants "
United States
Blanca L
The price is €198
includes taxes & fees
12 Apr - 13 Apr
Le Méridien Essex 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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Westchester

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

Schiller Woods view in Chicago of Illinois

Top Westchester Hotel Reviews

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 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?
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Westchester is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 3 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?
Hilton Chicago/Magnificent Mile Suites: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North and The Wade 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 Wrigley Field, United Center 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?
Wrigley Field, United Center 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.

Explore a world of travel with Expedia