Westchester Hotels from S$82

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Check prices for these dates

Tonight
29 Jun - 30 Jun
Tomorrow
30 Jun - 1 Jul
Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul

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Top 10 trending Westchester hotels

Four Points by Sheraton Chicago Westchester/Oak Brook
Lobby

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
8.4 out of 10, Very good, (1004)
"The hotel was wonderful!"
The price is S$136
includes taxes & fees
7 Jul - 8 Jul
Four Points by Sheraton Chicago Westchester/Oak Brook
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2048)
"Amazing stay"
The price is S$311
includes taxes & fees
6 Jul - 7 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Reception

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2297)
"It was a great stay! "
The price is S$239
includes taxes & fees
30 Jun - 1 Jul
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1476)
"Great location and rooms "
The price is S$294
includes taxes & fees
30 Jun - 1 Jul
Loews Chicago Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1884)
"Very nice hotel and very clean"
The price is S$214
includes taxes & fees
6 Jul - 7 Jul
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1466)
"Stayed here a few times and its always great. "
The price is S$341
includes taxes & fees
6 Jul - 7 Jul
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Executive lounge

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1789)
"Great stay, great location and very polite staff "
The price is S$319
includes taxes & fees
1 Jul - 2 Jul
Fairmont Chicago at Millennium Park
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.6 out of 10, Excellent, (1002)
"The Ivy Hotel was so nice! It was very roomy and had everything to make our stay convenient and special! "
The price is S$202
includes taxes & fees
2 Jul - 3 Jul
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1861)
"Very clean, great location and very friendly staff. "
The price is S$212
includes taxes & fees
6 Jul - 7 Jul
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3245)
"Great stay would stay again "
The price is S$315
includes taxes & fees
30 Jun - 1 Jul
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2352)
"Great stay "
The price is S$215
includes taxes & fees
6 Jul - 7 Jul
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.4 out of 10, Very good, (1858)
"Very historic place, nice rooms, staff was helpful, great for a short stay"
The price is S$220
includes taxes & fees
1 Jul - 2 Jul
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Premium bedding, pillow-top beds, in-room safe, desk

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1020)
"Very nice hotel - lots of amenities and in a good neighborhood and very close to shopping"
The price is S$255
includes taxes & fees
6 Jul - 7 Jul
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Restaurant

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1094)
"Lovely stay in the king suite. "
The price is S$215
includes taxes & fees
30 Jun - 1 Jul
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1637)
"Great stay"
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2083)
"Absolutely stunning place to stay. "
The price is S$229
includes taxes & fees
30 Jun - 1 Jul
Hotel Riu Plaza Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2537)
"Great stay"
The price is S$177
includes taxes & fees
7 Jul - 8 Jul
Best Western Grant Park Hotel
Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8890)
"Location of the property was excellent. Enjoyed our stay. "
The price is S$214
includes taxes & fees
3 Jul - 4 Jul
Congress Plaza Hotel
Le Méridien Essex Chicago
City view

Le Méridien Essex Chicago

4.0 star property
8.6 out of 10, Excellent, (1004)
"Location is great and property was very clean "
The price is S$217
includes taxes & fees
30 Jun - 1 Jul
Le Méridien Essex Chicago
InterContinental Chicago Magnificent Mile by IHG
Exterior

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (1932)
"Great hotel will be returning soon."
The price is S$276
includes taxes & fees
1 Jul - 2 Jul
InterContinental Chicago Magnificent Mile by IHG
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

Frequently asked questions

What's the best place to stay in Westchester?

Located 13.3 mi (21.4 km) from the heart of Westchester, Embassy Suites by Hilton Chicago Downtown River North is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are InterContinental Chicago Magnificent Mile by IHG and Hilton Chicago/Magnificent Mile Suites. See all available top hotels, or 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's the best accommodation for a golf trip to Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a hotel featuring free WiFi and pillowtop beds, and it's a top choice for playing a round of golf. See more golf hotels 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. Features full, an indoor pool and flat-screen televisions. InterContinental Chicago Magnificent Mile by IHG 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, Michigan Avenue and Soldier Field. In Westchester, there are 8 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 Soldier Field are some of the notable places to visit in the surrounding area. Additionally, you'll find Navy Pier and United Center 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.