Westchester hotels from HK$545

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Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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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)
"Central location for my trip"
United States
James
The price is HK$862
HK$965 total
includes taxes & fees
14 Jun - 15 Jun
Four Points by Sheraton Chicago Westchester/Oak Brook
Lobby

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago
4.0 star property
Rosemont
8.8 out of 10, Excellent, (2,585 reviews)
"The breakfast is always exceptional. "
United States
Kimberly
The price is HK$1,324
HK$1,509 total
includes taxes & fees
21 Jun - 22 Jun
Hyatt Regency O'Hare Chicago
Exterior

Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport
3.0 star property
Rosemont
8.4 out of 10, Very good, (3,390 reviews)
"Great place to stay"
United States
abhishek
The price is HK$1,214
HK$1,384 total
includes taxes & fees
28 Jun - 29 Jun
Hyatt Place Chicago/O'Hare Airport
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, (1,512 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is HK$1,225
HK$1,456 total
includes taxes & fees
22 Jun - 23 Jun
The Chicago Hotel Collection Ambassador Gold Coast
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (3,040 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is HK$1,223
HK$1,826 total
includes taxes & fees
10 Jun - 11 Jun
Freehand Chicago
Restaurant

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,495 reviews)
"Great location and super nice hotel"
United States
Karolina
The price is HK$2,108
HK$2,739 total
includes taxes & fees
21 Jun - 22 Jun
Sofitel Chicago Magnificent Mile
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, (2,012 reviews)
"Clean quiet hotel"
United States
Daniel
The price is HK$1,825
HK$2,169 total
includes taxes & fees
15 Jun - 16 Jun
Hilton Garden Inn Chicago Downtown South Loop
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,269 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is HK$1,873
HK$2,450 total
includes taxes & fees
16 Jun - 17 Jun
Hotel Riu Plaza Chicago
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,643 reviews)
"Beautiful views"
United States
Dominique
The price is HK$2,578
HK$3,344 total
includes taxes & fees
14 Jun - 15 Jun
Sheraton Grand Chicago Riverwalk
Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,491 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is HK$1,678
HK$1,995 total
includes taxes & fees
14 Jun - 15 Jun
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (1,001 reviews)
"Room was beautiful and bar was extremely nice"
United States
Rebekah
The price is HK$2,656
HK$3,158 total
includes taxes & fees
13 Jun - 14 Jun
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Property entrance

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,031 reviews)
"Great location right off magnificent mile and close to everything. "
United States
Natalia
The price is HK$1,175
HK$1,627 total
includes taxes & fees
28 Jun - 29 Jun
Warwick Allerton - Chicago
Exterior

Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,322 reviews)
"Overall great stay."
United States
Timothy
The price is HK$1,857
HK$2,208 total
includes taxes & fees
28 Jun - 29 Jun
Hyatt Place Chicago/Downtown - The Loop
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, (1,076 reviews)
"Clean rooms, comfy bed."
United States
Brenda
The price is HK$1,951
HK$2,552 total
includes taxes & fees
28 Jun - 29 Jun
Staypineapple, An Iconic Hotel, The Loop
Lobby lounge

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,000 reviews)
"Would definitely stay here again! Clean, friendly staff, great location."
United States
Heather
The price is HK$1,810
HK$2,291 total
includes taxes & fees
28 Jun - 29 Jun
Le Méridien Essex Chicago
Exterior

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, (2,787 reviews)
"Very clean room, nice breakfast and really nice hotel restaurant"
United States
Hugo
The price is HK$1,727
HK$2,191 total
includes taxes & fees
28 Jun - 29 Jun
La Quinta Inn & Suites by Wyndham Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,240 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is HK$1,253
HK$1,728 total
includes taxes & fees
28 Jun - 29 Jun
Silversmith Hotel Chicago Downtown
Bar (on property)

Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,493 reviews)
"Huge rooms and great location"
United States
nicolette
The price is HK$1,747
HK$2,077 total
includes taxes & fees
28 Jun - 29 Jun
Canopy by Hilton Chicago Central Loop
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,110 reviews)
"Very beautiful hotel!"
United States
Ingrid
The price is HK$1,897
HK$2,492 total
includes taxes & fees
14 Jun - 15 Jun
Arlo Chicago
Exterior

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, (2,861 reviews)
"Breakfast was excellent."
United States
Janine
The price is HK$1,725
HK$2,280 total
includes taxes & fees
28 Jun - 29 Jun
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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.

See all hotels in Westchester
Schiller Woods view in Chicago of Illinois

Top Westchester Hotel Reviews

River Hotel

River Hotel

6/10 Okay
"The WiFi was not good. Very slow and not helpful. Everything else about the stay was great"
Jacob 4-night trip
Posted 2 hours ago
River Hotel

More cheap stays in Westchester

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

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

22 West Algonquin Road Arlington Heights IL
The price is HK$486 per night from 11 Jun to 12 Jun
HK$486
HK$545 total
11 Jun - 12 Jun
includes taxes & fees
5.4/10 (1,001 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 Hotel Riu Plaza Chicago and The Chicago Hotel Collection - Magnificent Mile. 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. Offers 2 restaurants, an indoor pool and a sauna. Aloft by Marriott Chicago Mag Mile and Hilton Chicago/Magnificent Mile Suites 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, 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.

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