Westchester Hotels from S$68

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Our top choices for Westchester hotels

Breakfast and dinner served
Four Points by Sheraton Chicago Westchester/Oak Brook

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, (1010)
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 S$145
includes taxes & fees
19 Jan - 20 Jan, 2026
Four Points by Sheraton Chicago Westchester/Oak Brook
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3533)
Stylish hotel minutes from Chicago Riverwalk and Merchandise Mart with convenient access to public transit. Relax in the indoor pool, sauna, and bar after exploring Michigan Avenue, or maintain routines at the 24-hour fitness centre.
"Really nice hotel"
United States
Saulius
The price is S$175
includes taxes & fees
26 Jan - 27 Jan, 2026
voco Chicago Downtown - Riverwalk by IHG
Reception
River Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4871)
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.
"Clean friendly hotel "
United States
maria
The price is S$110
includes taxes & fees
24 Jan - 25 Jan, 2026
River Hotel
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2996)
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 S$130
includes taxes & fees
22 Jan - 23 Jan, 2026
Aloft Chicago Mag Mile
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1800)
Immersive experience in city centre Chicago with both indoor and seasonal outdoor pools. FireLake restaurant serves lunch and dinner, while the 24-hour fitness centre keeps you energised near Michigan Avenue attractions.
"Great hotel, close to shopping and restaurants, excellent customer service, highly recommend."
United States
Gina
The price is S$235
includes taxes & fees
2 Jan - 3 Jan, 2026
Radisson Blu Aqua Hotel Chicago
American cuisine, al fresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1953)
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 S$174
includes taxes & fees
20 Jan - 21 Jan, 2026
The Godfrey Hotel Chicago
Premium bedding, down duvets, pillow-top beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1545)
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.
"Great staff and great location. "
United States
Joe
The price is S$140
includes taxes & fees
4 Jan - 5 Jan, 2026
The Wade
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent 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, (2211)
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.
"It was a beautiful stay "
United States
Donald
The price is S$129
includes taxes & fees
4 Jan - 5 Jan, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Breakfast, lunch and dinner served
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3333)
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.
"Great hotel "
United States
Anthony
The price is S$123
includes taxes & fees
11 Jan - 12 Jan, 2026
Club Quarters Hotel, Central Loop, Chicago
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3401)
Immerse yourself in Chicago's energy at this centrally located hotel. Just steps from Michigan Avenue Bridge and Chicago Riverwalk, enjoy 4 restaurants, 2 coffee shops, and stunning city views. Millennium Station is only a 7-minute walk away.
"The Hotel was amazing great location "
United States
Donnisha
The price is S$255
includes taxes & fees
20 Jan - 21 Jan, 2026
Hyatt Regency Chicago
Exterior
AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1010)
"Great location."
United States
Jeremy
The price is S$152
includes taxes & fees
29 Jan - 30 Jan, 2026
AC Hotels by Marriott Chicago Downtown
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3174)
Immerse yourself in Chicago's heartbeat at this boutique hotel, just a 5-minute walk from Michigan Avenue and State Street. Unwind at the full-service spa, workout in the fitness centre, or rejuvenate in the sauna. Chicago Station is only 3 minutes away.
"stunning hotel"
Canada
Yiwei
The price is S$141
includes taxes & fees
27 Jan - 28 Jan, 2026
Eurostars Magnificent Mile
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, 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, (2019)
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 S$111
includes taxes & fees
24 Jan - 25 Jan, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Snack bar
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1478)
Located in Chicago's Theatre District, this hotel offers comfortable beds and a health club. Grab a bite at Intermission restaurant or the bar. Lake Station is steps away, with Chicago Riverwalk and Millennium Park nearby. The helpful staff ensures a memorable stay.
"The staff was super friendly at check-in and the bartender was very nice!"
United States
Jennifer
The price is S$135
includes taxes & fees
11 Jan - 12 Jan, 2026
Cambria Hotel Chicago Loop - Theatre District
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3452)
Perfectly situated near Chicago Riverwalk, this boutique hotel offers stunning views, a 24-hour fitness centre, and Korean dining at Perilla Steak. Just steps from Michigan Avenue and minutes from public transit, enjoy a quiet, relaxing atmosphere with excellent coffee service.
"Amazing place to stay and super accommodating "
United States
Carson
The price is S$212
includes taxes & fees
12 Jan - 13 Jan, 2026
L7 Chicago by LOTTE
Lobby
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2008)
This historic gem sits steps from Lake Michigan, offering effortless access to Chicago's vibrant attractions. The 24-hour fitness centre complements comfortable beds and attentive staff service. Guests praise the quiet atmosphere and convenient transit connections to explore the city.
"Very clean, quiet, and warm reception and service from the staff. "
United States
tim
The price is S$164
includes taxes & fees
2 Jan - 3 Jan, 2026
Millennium Knickerbocker Chicago
Lobby
Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1353)
"Had the best stay here! Would definitely stay here again! "
United States
Nancy
The price is S$129
includes taxes & fees
4 Jan - 5 Jan, 2026
Hampton Inn & Suites Chicago Downtown
Premium bedding, pillow-top beds, minibar, in-room safe
Kinzie Hotel

Kinzie Hotel

Kinzie Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2036)
Sophisticated accommodation mere minutes from Chicago Theatre and Merchandise Mart. Enjoy daily breakfast, fitness centre access, and convenient room service. The Grand Station Red Line is just 4 minutes away, connecting you to Chicago's iconic attractions.
"I liked the hospitality of the staff, and I felt that the location was pretty good! "
South Korea
KYOUNGJOO
The price is S$225
includes taxes & fees
2 Jan - 3 Jan, 2026
Kinzie Hotel
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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, (4287)
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 S$117
includes taxes & fees
4 Jan - 5 Jan, 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1060)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is S$185
includes taxes & fees
4 Jan - 5 Jan, 2026
Hyatt Centric Chicago 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.

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Schiller Woods view in Chicago of Illinois

Top Westchester Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"When I pulled up I was wholeheartedly greeted by the doorman. Upon entering the hotel it was a joyful and friendly atmosphere. The receptionist was very courteous and professional. I’ve stayed here multiply times and have been very satisfied. Will return again. One more thing, the hotel is in a great location."
Margo 3-night trip
Posted 1 day ago
The Royal Sonesta Chicago Downtown

More cheap stays in Westchester

Motel 6 Naperville, IL

Motel 6 Naperville, IL

1585 Naperville Wheaton Road Naperville IL
The price is S$68 per night from 13 Jan to 14 Jan
S$68
13 Jan - 14 Jan, 2026
includes taxes & fees
7.8/10 Good! (1,168 reviews)

Frequently asked questions

What's the best place to stay in Westchester?
Located 13.7 mi (22.1 km) from the heart of Westchester, Hilton Chicago/Magnificent Mile Suites is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Palmer House a Hilton Hotel and Silversmith Hotel Chicago Downtown. 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 are some accommodation options with pools in Westchester?
Palmer House a Hilton Hotel: Hotel steps from State Street. Offers a full-service spa, an indoor pool and a 24-hour fitness centre. Hilton Chicago 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 10 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.

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