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Jul 21 - Jul 22
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Top 10 trending Westchester hotels

FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very Good, (139)
"Great area and friendly staff...also check in was extremely easy!"
The price is P7,009
P8,228 total
includes taxes & fees
Aug 6 - Aug 7
FOUND Hotel Chicago River North
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1009)
"Great place to stay!"
The price is P7,549
P8,862 total
includes taxes & fees
Aug 17 - Aug 18
Ohio House Motel
Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1009)
"Great stay"
The price is P8,693
P10,205 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express Chicago - Magnificent Mile by IHG
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 P5,662
P6,340 total
includes taxes & fees
Aug 4 - Aug 5
Four Points by Sheraton Chicago Westchester/Oak Brook
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2571)
"Excellent Hotel!!"
The price is P8,216
P9,645 total
includes taxes & fees
Aug 14 - Aug 15
Best Western Grant Park Hotel
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2256)
"Best Travelodge I have stayed at "
The price is P7,309
P8,580 total
includes taxes & fees
Aug 18 - Aug 19
Travelodge by Wyndham Downtown Chicago
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2090)
"Stayed many times, great fun!"
The price is P6,251
P10,024 total
includes taxes & fees
Aug 17 - Aug 18
Freehand Chicago
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1294)
"Great location and hotel "
The price is P9,380
P11,011 total
includes taxes & fees
Aug 10 - Aug 11
Crowne Plaza Chicago West Loop by IHG
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (244)
"Great location, nice amenities"
Level Chicago Fulton Market
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8922)
"Great place to stay."
The price is P10,145
P11,910 total
includes taxes & fees
Aug 4 - Aug 5
Congress Plaza Hotel
Residence Inn Chicago Downtown Magnificent Mile
Aerial view

Residence Inn Chicago Downtown Magnificent Mile

4.0 star property
9.6 out of 10, Exceptional, (304)
"This was a great hotel in a great location."
The price is P11,133
P13,069 total
includes taxes & fees
Aug 7 - Aug 8
Residence Inn Chicago Downtown Magnificent Mile
Club Quarters Hotel, Central Loop, Chicago
Breakfast, lunch and dinner served

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3349)
"Great location and nice rooms. "
The price is P8,575
P10,066 total
includes taxes & fees
Jul 27 - Jul 28
Club Quarters Hotel, Central Loop, Chicago
The Hoxton Chicago
3 bars/lounges, piano bar

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1005)
"Excellent location and great vibe. "
The price is P11,953
P14,032 total
includes taxes & fees
Aug 17 - Aug 18
The Hoxton Chicago
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (526)
"The rooms were excellent"
The price is P5,817
P11,523 total
includes taxes & fees
Jul 23 - Jul 24
The Chicago Hotel Collection River North
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1018)
"nice hotel and nice staff and close to everything "
The price is P7,730
P9,074 total
includes taxes & fees
Aug 17 - Aug 18
Best Western River North Hotel
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1814)
"Nice room, great location and excellent staff."
The price is P8,575
P10,066 total
includes taxes & fees
Jul 27 - Jul 28
Central Loop Hotel
The Emily Hotel
Exterior

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1140)
"Great place"
The price is P17,560
P20,614 total
includes taxes & fees
Aug 21 - Aug 22
The Emily Hotel
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2010)
"Great stay! "
The price is P11,768
P15,493 total
includes taxes & fees
Aug 9 - Aug 10
Hilton Chicago
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1260)
"Great breakfast options and welcoming vibe. Amazing location and overall great value."
The price is P8,312
P11,437 total
includes taxes & fees
Aug 17 - Aug 18
Claridge House
Millennium Knickerbocker Chicago
Lobby

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1898)
"It was a wonderful stay"
The price is P7,264
P9,870 total
includes taxes & fees
Aug 13 - Aug 14
Millennium Knickerbocker 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.
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Learn more about Westchester

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

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Top Westchester Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Amazing location, clean room"
Demetria 5-night trip
Posted 20 hours ago
Hilton Chicago/Magnificent Mile Suites

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 traveler data. Other good options for your trip to 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! The majority of hotel reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Westchester.

Where can I learn more about changing or cancelling my trip to Westchester?

To access more information about updating your trip to Westchester or cancelling it, click here.

What is the top LGBTQ-friendly place to stay in Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a top LGBTQ-friendly hotel, and features free WiFi and pillowtop beds. See all available hotels listed as LGBTQ-friendly in Westchester.

What's the best pet-friendly accommodation in Westchester?

Four Points by Sheraton Chicago Westchester/Oak Brook is a top hotel for people traveling with their pets, and offers a restaurant and a fitness center for its human guests. See more pet-friendly hotel accommodations in Westchester.

Where is the best hotel to stay close to Fresh Meadow Golf Club?

Four Points by Sheraton Chicago Westchester/Oak Brook is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and free WiFi. It's located just a short 0.4 mi (0.7 km) from Fresh Meadow Golf Club. Other good options within 5 miles include Hyatt House Oak Brook and Holiday Inn Express Hotel & Suites Chicago West-O'hare Arpt.

What's the best place to stay if I'm looking to play golf in 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 accommodations with pools in Westchester?

InterContinental Chicago Magnificent Mile by IHG: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a steam room. Another choice with an onsite pool is Embassy Suites by Hilton Chicago Downtown River North. View all hotels with pools in Westchester.

What's the best accommodation near O'Hare International Airport (ORD)?

Hilton Chicago O'Hare Airport is a popular 4-star hotel featuring 2 restaurants and 2 bars. It's located a short 0.1 mi (0.1 km) from O'Hare Intl. Airport. Other good options close to the airport are Edward Hotel Chicago and Best Western At O'Hare.

How is it to stay in Westchester?

Visitors to Westchester are sure to 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 Navy Pier. In Westchester, there are 8 hotels and other accommodations to choose from. Find out more about Westchester.

What should I see while I'm in Westchester?

Wrigley Field, Michigan Avenue, and Navy Pier are some of the notable places to visit in the surrounding area. Additionally, you'll find United Center and Soldier Field in the area. Check out what more to see and do in Expedia's Westchester guide.

What's the seasonal weather like in Westchester?

The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.