Westchester Hotel & Accommodation Deals 2026 from NZ$110 - Fully Refundable Options

Our top choices for Westchester hotels

Four Points by Sheraton Chicago Westchester/Oak Brook

Westchester

Gerald Michael

includes taxes & fees

7 June - 8 June

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

includes taxes & fees

26 May - 27 May

River Hotel

Downtown Chicago

Jaeyoung

includes taxes & fees

26 May - 27 May

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Robin

includes taxes & fees

22 June - 23 June

Congress Plaza Hotel

Downtown Chicago

Jennifer

includes taxes & fees

25 May - 26 May

Silversmith Hotel Chicago Downtown

Downtown Chicago

Brittany

includes taxes & fees

26 May - 27 May

Palmer House a Hilton Hotel

Downtown Chicago

Teresa

includes taxes & fees

26 May - 27 May

Hotel Riu Plaza Chicago

Downtown Chicago

sierra

includes taxes & fees

27 May - 28 May

Sports Illustrated Resorts Chicago

Downtown Chicago

Erik

includes taxes & fees

26 May - 27 May

The Wade

Downtown Chicago

Molly

includes taxes & fees

25 May - 26 May

Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Jimmie

includes taxes & fees

26 May - 27 May

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Grisel

includes taxes & fees

25 May - 26 May

Freehand Chicago

Downtown Chicago

Michael

includes taxes & fees

25 May - 26 May

2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Matson

includes taxes & fees

25 May - 26 May

Club Quarters Hotel Wacker at Michigan, Chicago

Downtown Chicago

Radhika

includes taxes & fees

26 May - 27 May

Fairmont Chicago at Millennium Park

Downtown Chicago

JOSE

includes taxes & fees

25 May - 26 May

The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Ontario

includes taxes & fees

25 May - 26 May

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Downtown Chicago

Nicholas

includes taxes & fees

25 May - 26 May

Eurostars Magnificent Mile

Downtown Chicago

Belinda

includes taxes & fees

25 May - 26 May

Swissotel - Chicago

Downtown Chicago

Sridhar

includes taxes & fees

25 May - 26 May

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

Hilton Chicago

10/10 Excellent

"Beautiful hotel with a great central location to everything. Breakfast was one the best! Staff were wonderful, always asking to help out and very friendly! Would absolutely stay here again!"

Hilton Chicago/Magnificent Mile Suites

8/10 Good

"Beautiful hotel and amazing staff. However, in my first night, I talked housekeeping concierge and front desk when I realized pillows were feather. I'm am terribly allergic . Fell asleep waiting. Noone ever came. Woke with hives and eyes swollen shut. Was corrected the next night. But really ruined my trip. Symptoms still nut fully resolved despite a visit to UC and frequent medicines. Terrible."

Fairmont Chicago at Millennium Park

10/10 Excellent

"This is my new go-to-first choice hotel in Chicago. Location is centrally located, slightly off the beaten track, and unbelievably quiet. Staff is welcoming and especially kind. Very comfortable room with a bed that feels like sleeping on a cloud. The tub was unexpectedly long with a separate shower. Great valet service, very safe parking. Most of all… Safe!"

The Chicago Hotel Collection Ambassador Gold Coast

2/10 Terrible

"The hotel is filthy dirty with no fire extinguishers. There’s no soap in the rooms. I had an expensive suite I stayed here for seven days. The service at the hotel doesn’t bring towels, soap or shampoo. There’s no hot water. They do not clean the rooms and the hallways of filthy dirty, and everyone is smoking in the hotels. Then I went down in the elevator to switch rooms cause I had no hot water and I had my carry-on suitcase in the center of the elevator, and the door slammed on the suitcase, knocked it over and my hand was caught in the elevator. I pushed the emergency button and it didn’t work. The elevators are out of code and I’ve never replaced in 30 years is it dangerous situation you should I want a refund from staying at this hotel when I went to the front desk I asked for an ice pack and they said they have no ice. I asked them to put ice in the bag and they refused to they stay off is rude as hell and everyone in the hotel is terrible. It’s a dangerous situation and the hotel should be closed down and Hotel.com should not recommend this as a place to stay."

More cheap accommodation in Westchester

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

22 West Algonquin Road Arlington Heights IL

NZ$110

10 June - 11 June

includes taxes & fees

5.4/10 (1,003 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

Book Hotels in Westchester on Expedia.com

Search Westchester hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Westchester

Check prices for these dates

Filter by

Our top choices for Westchester hotels

Four Points by Sheraton Chicago Westchester/Oak Brook

Sable at Navy Pier Chicago, Curio Collection by Hilton

River Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Congress Plaza Hotel

Silversmith Hotel Chicago Downtown

Palmer House a Hilton Hotel

Hotel Riu Plaza Chicago

Sports Illustrated Resorts Chicago

The Wade

Aloft by Marriott Chicago Mag Mile

Sheraton Grand Chicago Riverwalk

Freehand Chicago

LondonHouse Chicago, Curio Collection by Hilton

Club Quarters Hotel Wacker at Michigan, Chicago

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection - Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Eurostars Magnificent Mile

Swissotel - Chicago

Learn more about Westchester

Top Westchester Hotel Reviews

Hilton Chicago

More cheap accommodation in Westchester

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

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app