Search Westchester hotels

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

This weekend
Next weekend

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, (1002)
Escape to a tranquil setting with easy access to Chicago attractions. This Westchester hotel offers complimentary WiFi and parking, plus a fitness centre for active travellers. Enjoy breakfast or dinner at 2222 Restaurant & Lounge after exploring nearby Oak Brook Golf Course.

"Thanks, great stay"
United States
Robert
The price is NZ$195
includes taxes & fees
14 Jan - 15 Jan
Four Points by Sheraton Chicago Westchester/Oak Brook

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2692)
Feel the pulse of the city at this Art Deco gem with Grand Station at your doorstep. Enjoy a workout in the 24-hour fitness centre, then relax at the bar or café. Michigan Avenue shopping, Millennium Park, and Chicago Riverwalk await nearby.

"Great fun place to stay close to most things in downtown "
United States
Kayla
The price is NZ$141
includes taxes & fees
1 Feb - 2 Feb
Freehand Chicago

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4886)
Strategically positioned near Michigan Avenue, this hotel offers business travellers easy access to Chicago Riverwalk and Millennium Park. Enjoy free WiFi, convenient room service, and a fitness centre while Clark-Lake Station is just 7 minutes away.

"Would stay there again"
United States
Zach
The price is NZ$166
includes taxes & fees
20 Jan - 21 Jan
River Hotel

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3121)
"Second time to stay here, everything is great!"
United States
Wei
The price is NZ$233
includes taxes & fees
8 Jan - 9 Jan
Hotel Riu Plaza Chicago

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1514)
Enjoy facials and manicures at this tranquil urban retreat just minutes from Clark-Division Station. The coffee shop transforms into an evening cocktail bar, while Michigan Avenue and Chicago Riverwalk wait to be explored nearby.

"Very nice and quiet, excellent location"
United States
Anthony
The price is NZ$174
includes taxes & fees
1 Feb - 2 Feb
Claridge House Chicago, Tapestry Collection by Hilton

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3011)
Experience modern comfort in city centre Chicago with an indoor pool and on-site American restaurant. Just a 10-minute walk from Michigan Avenue and close to Grand Station, this hotel offers a fitness centre and bar for your urban adventure.

"Great place to stay"
United States
Elisha
The price is NZ$170
includes taxes & fees
22 Jan - 23 Jan
Aloft Chicago Mag Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2221)
Located in bustling city centre, this hotel offers stunning city views from select rooms. The outdoor pool and rooftop terrace create a refreshing escape after exploring Michigan Avenue and Chicago Riverwalk. Starbucks in the lobby and Grand Station just 9 minutes away enhance the convenient experience.

"Fantastic stay! Looking forward to staying here again!!"
United States
Amber
The price is NZ$173
includes taxes & fees
13 Jan - 14 Jan
DoubleTree by Hilton Chicago - Magnificent Mile

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3016)
This historic Chicago hotel offers amazing views and a quiet, relaxing atmosphere. Just 6 minutes from Chicago Station and near the Riverwalk, guests enjoy a 24-hour fitness centre and convenient bar/lounge after a day of city exploration.

"Every thing is perfect, the location, safe for solo travel. "
United States
Ken
The price is NZ$175
includes taxes & fees
6 Feb - 7 Feb
Warwick Allerton - Chicago

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1576)
Experience Chicago's allure at this elegant hotel near Michigan Avenue and Lake Michigan. Guests rave about the quiet rooms, stunning lake views, and proximity to Navy Pier. Enjoy American cuisine at Current restaurant after unwinding in the indoor pool.

"Easy check in and out, excellent room service and dining menu."
United States
Kevin Bradford
The price is NZ$205
includes taxes & fees
22 Jan - 23 Jan
The Wade

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very good, (3849)
This boutique hotel offers Japanese cuisine at Kirei restaurant and a peaceful retreat near Lake Michigan. Just 6 minutes from Chicago Station and within walking distance of shopping havens and tourist spots, its historic charm creates a relaxing atmosphere with magnificent views.

"great location"
Mexico
Isabel
The price is NZ$155
includes taxes & fees
13 Jan - 14 Jan
The Whitehall Hotel, BW Premier Collection

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2374)
"The staff was anmazing and the location within the city was great."
United States
Othon
The price is NZ$255
includes taxes & fees
17 Jan - 18 Jan
The Royal Sonesta Chicago River North

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1976)
Perched just steps from Michigan Avenue and Chicago Riverwalk, this hotel offers a tranquil rooftop terrace. Relax with deep-tissue massages at the full-service spa or energise in the 24-hour fitness centre. Two transit stations are only 6 minutes away.

"The room was nice, the area was perfect for walking distance for food and activities. "
United States
Alexis
The price is NZ$217
includes taxes & fees
1 Feb - 2 Feb
The Godfrey Hotel Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2046)
Located in the heart of Chicago, this hotel offers easy access to the Riverwalk and Chicago Theatre. Clean rooms provide comfort after exploring Michigan Avenue and Millennium Park. State Station is just 4 minutes away for convenient city adventures.

"Great stay"
United States
Kramer
The price is NZ$166
includes taxes & fees
20 Jan - 21 Jan
Club Quarters Hotel Wacker at Michigan, Chicago

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3665)
"Great hotel!"
United States
William
The price is NZ$181
includes taxes & fees
13 Jan - 14 Jan
Hilton Chicago/Magnificent Mile Suites

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4168)
Immerse yourself in Chicago's energy at this modern hotel near Michigan Avenue. Enjoy international cuisine at the restaurant, unwind at the bar, or work out in the gym. Just minutes from Chicago Riverwalk and two train stations for seamless city exploration.

"Stay was great and in a great location!! "
United States
Ashley
The price is NZ$209
includes taxes & fees
29 Jan - 30 Jan
citizenM Chicago Downtown

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4328)
Immerse yourself in the heart of Chicago at this centrally located hotel. Just a 1-minute walk from Grand Station and 5 minutes from Michigan Avenue, enjoy the indoor pool, Weber Grill restaurant, and bar after a day of sightseeing.

"Amazing staff and perfect location "
United States
Brandi
The price is NZ$158
includes taxes & fees
25 Jan - 26 Jan
Hilton Garden Inn Chicago Downtown/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, (2324)
Experience waterfront elegance at this Curio Collection hotel directly on Navy Pier. Just steps from Lake Michigan, guests enjoy Latin flavours at Lirica restaurant, 2 stylish bars, and a 24-hour fitness centre. Michigan Avenue shopping and convenient transit options enhance this prime Chicago location.

"Great stay!"
United States
Angela
The price is NZ$264
includes taxes & fees
13 Jan - 14 Jan
Sable at Navy Pier Chicago, Curio Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1931)
Steps from Grand Station, this Chicago boutique hotel offers an artsy urban retreat with a welcoming bar/lounge and fitness centre. Just minutes from Millennium Park and Chicago Riverwalk, guests praise the comfortable beds and attentive staff.

"Love the location, room, staff, and bar."
United States
Jason
The price is NZ$148
includes taxes & fees
13 Jan - 14 Jan
ACME Hotel Chicago, Outset Collection by Hilton

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3368)
Experience urban convenience at this city centre hotel, just a 5-minute walk from Willis Tower. The Jackson Station is only 3 minutes away, with Millennium Park and Art Institute within a 10-minute stroll. Enjoy the 24-hour fitness centre and on-site restaurant.

"Nice Hotel, convenient location fot shopping and walking around"
United States
Kerima
The price is NZ$169
includes taxes & fees
8 Jan - 9 Jan
Club Quarters Hotel, Central Loop, Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1926)
Unwind at this perfectly positioned Chicago hotel, just minutes from Millennium Park and Michigan Avenue. The American restaurant, fitness centre, and room service add convenience while the Randolph-Wabash Station sits right outside for easy city exploration.

"Clean and comfy room, friendly staff, great location. "
United States
Agata
The price is NZ$248
includes taxes & fees
6 Feb - 7 Feb
Arlo 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

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

Schiller Woods view in Chicago of Illinois

Top Westchester Hotel Reviews

More cheap accommodation in Westchester

Frequently asked questions

What's the best place to stay in Westchester?
Located 13.3 mi (21.3 km) from the heart of Westchester, Hilton Chicago 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 Palmer House a Hilton Hotel. See all available top hotels, or vacation rentals in Westchester.
What are some of the best holiday rentals that Westchester has to offer?
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!: This holiday home rental outside of Westchester is on a lake, and equipped with 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?
Hilton Chicago: Hotel, 4-minute walk from State Street. Features 2 restaurants, an indoor pool and a health club. Palmer House a Hilton Hotel and Embassy Suites by Hilton Chicago Downtown River North 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, Michigan Avenue and United Center. In Westchester, there are 11 hotels and other accommodation options to choose from. Find out more about Westchester.
What should I see while I'm in Westchester?
Wrigley Field, Michigan Avenue and United Center 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