Hotels in Westchester

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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, (1,001 reviews)
Quiet sanctuary in Westchester with easy drives to Oak Brook Golf Course and nearby forest preserves. This hotel offers free WiFi, complimentary parking, and a fitness center, plus on-site dining at 2222 Restaurant & Lounge for breakfast and dinner.
The price is $110
$123 total
includes taxes & fees
May 24 - May 25
Four Points by Sheraton Chicago Westchester/Oak Brook
SureStay Plus Hotel by Best Western Chicago Lombard
SureStay Plus Hotel by Best Western Chicago Lombard
2.5 star property
Highland Hills
9.0 out of 10, Wonderful, (2,737 reviews)
This quiet, comfortable hotel in Lombard offers a complimentary breakfast, free WiFi, and parking. Located near popular attractions and Lombard Station, it provides easy shopping access while maintaining a peaceful atmosphere praised by travelers.
The price is $88
$98 total
includes taxes & fees
May 26 - May 27
SureStay Plus Hotel by Best Western Chicago Lombard
The Hoxton Chicago
The Hoxton Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
Dive into Chicago's vibrant scene at this West Loop hotel with a seasonal rooftop pool and Mediterranean dining at Cira. Just minutes from Millennium Park and Chicago Riverwalk, with 3 bars, free bikes, and easy access to Clinton Station.
The price is $229
$302 total
includes taxes & fees
May 25 - May 26
The Hoxton Chicago
Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,246 reviews)
Just a short drive from United Center and Millennium Park, this hotel offers a 24-hour fitness center and on-site dining. Enjoy morning swims in the indoor pool, unwind at the bar, and appreciate the convenient walk to Ashland Station.
The price is $188
$224 total
includes taxes & fees
May 25 - May 26
Hyatt House Chicago/West Loop-Fulton Market
The Emily Hotel
The Emily Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,317 reviews)
The price is $272
$323 total
includes taxes & fees
May 25 - May 26
The Emily Hotel
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,175 reviews)
Modern downtown Chicago hotel with easy access to Millennium Park and Riverwalk. Grab American cuisine at Rye Deli & Drink, unwind at the bar, or maintain fitness routines in the workout center. Within 10 minutes of Ogilvie Transportation Center and Union Station.
The price is $135
$161 total
includes taxes & fees
May 25 - May 26
Crowne Plaza Chicago West Loop by IHG
Level Chicago Fulton Market
Level Chicago Fulton Market
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (479 reviews)
Immerse in urban flair at this Chicago hotel with an outdoor pool and free WiFi. Only a 5-minute drive from Michigan Avenue and Millennium Park, you're just 6 minutes from Grand Station for easy city exploration.
The price is $164
$218 total
includes taxes & fees
May 25 - May 26
Level Chicago Fulton Market
Hyatt Place Itasca
Hyatt Place Itasca
3.0 star property
Itasca
8.8 out of 10, Excellent, (1,089 reviews)
Serene hotel in a quiet area with indoor pool and bar for relaxation after exploring nearby Woodfield Mall and Schaumburg Convention Center. Enjoy complimentary breakfast, WiFi, and parking while the helpful staff ensures a comfortable business stay.
The price is $110
$122 total
includes taxes & fees
May 24 - May 25
Hyatt Place Itasca
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,002 reviews)
Wake up to a complimentary breakfast at this Chicago West Loop hotel near Clinton Station. An indoor pool and 24-hour fitness center await after exploring nearby Merchandise Mart and Willis Tower. Convenient rooms include sofa beds and refrigerators for extended comfort.
The price is $147
$174 total
includes taxes & fees
May 26 - May 27
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Hampton Inn Chicago West Loop Fulton Market Area
Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,001 reviews)
Experience Chicago's vibrant energy from this well-located hotel near Willis Tower. Enjoy the rooftop terrace after a refreshing swim or workout in the 24-hour fitness center. Just 4 minutes from Clinton Station, with free breakfast to fuel your urban adventures.
The price is $161
$191 total
includes taxes & fees
May 25 - May 26
Hampton Inn Chicago West Loop Fulton Market Area
Canopy by Hilton Chicago Central Loop
Canopy by Hilton Chicago Central Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,485 reviews)
Experience Chicago's vibrant heart at this hotel, just a 10-minute walk from Willis Tower and State Street. Grab a bite at the restaurant, workout at the fitness center, or unwind at the bar. With Quincy Metro Station right outside, exploring Millennium Park and Chicago Riverwalk is effortless.
The price is $163
$194 total
includes taxes & fees
May 25 - May 26
Canopy by Hilton Chicago Central Loop
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,002 reviews)
Steps from Clinton Station, this hotel offers a seasonal outdoor pool and 24-hour health club for active travelers. Enjoy the terrace and snack bar, or walk to Chicago Union Station and Millennium Park. Guests rave about the helpful staff and clean rooms.
The price is $118
$152 total
includes taxes & fees
May 25 - May 26
Holiday Inn & Suites Chicago - Downtown by IHG
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,446 reviews)
Immerse yourself in luxury at this storied Chicago hotel. Just steps from Millennium Park and Monroe Station, this classic retreat features a full-service spa, indoor pool, and elegant bar. Travelers praise the central location and helpful staff.
The price is $151
$209 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (605 reviews)
Located in Chicago's River North area, this inviting hotel offers free WiFi and 24-hour front desk service. Just 5 minutes from Merchandise Mart Station and a short stroll to State Street, you're perfectly positioned to explore Michigan Avenue and Chicago Riverwalk.
The price is $102
$119 total
includes taxes & fees
May 25 - May 26
FOUND Hotel Chicago River North
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, (2,775 reviews)
Steps from Willis Tower and a short walk to Michigan Avenue, this hotel offers free breakfast and WiFi. The fitness center keeps you active, while 2 restaurants provide dining options. Washington-Wells Station is just 3 minutes away.
The price is $130
$172 total
includes taxes & fees
May 25 - May 26
La Quinta Inn & Suites by Wyndham Chicago Downtown
Level Chicago - River North
Level Chicago - River North
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,003 reviews)
Steps from Merchandise Mart, this hotel offers a seasonal outdoor pool and fitness center to keep you active. Free WiFi awaits while Michigan Avenue and Chicago Riverwalk are just a 5-minute drive away. Merchandise Mart Station is only 8 minutes on foot.
The price is $165
$219 total
includes taxes & fees
May 25 - May 26
Level Chicago - River North
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (1,231 reviews)
Central Chicago location puts Millennium Park, Art Institute, and Willis Tower within a 15-minute walk. Guests love the peaceful rooms, 24-hour fitness center, and regional cuisine at Meli Cafe. Just minutes from multiple transit options for effortless city exploration.
The price is $159
$189 total
includes taxes & fees
May 25 - May 26
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Hyatt Place Chicago/O'Hare Airport
Hyatt Place Chicago/O'Hare Airport
3.0 star property
Rosemont
8.4 out of 10, Very Good, (3,365 reviews)
Just 3.4 mi from O'Hare Airport, this Rosemont hotel balances convenience with tranquility. Enjoy the indoor pool and 24/7 restaurant after using the complimentary airport shuttle. Within 15 minutes of public transit and near Allstate Arena.
The price is $110
$125 total
includes taxes & fees
May 25 - May 26
Hyatt Place Chicago/O'Hare Airport
Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central Loop
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,347 reviews)
Immerse yourself in Chicago from this central Loop hotel near Quincy Metro Station. Just a 10-minute walk to Willis Tower with 2 restaurants and 2 bars to enjoy after a workout in the fitness center. Clean rooms and helpful staff complete your stay.
The price is $155
$184 total
includes taxes & fees
May 25 - May 26
Hilton Garden Inn Chicago Central Loop
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,063 reviews)
The price is $139
$195 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop
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.

When is the best time to visit Westchester?

Our prices for hotels in Westchester are cheapest in December
Price trends for hotels in Westchester
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Westchester
May
High 19°C / low 11°C. Sunny most days.
View properties in May
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 27 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 24 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 16 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 9 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
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January, no crowd data, average high temperature -1 degrees Celsius, average low temperature -7 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 7 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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April, no crowd data, average high temperature 13 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
Monthly weather averages (˚C)

Learn more about Westchester

Wrigley Field, McCormick Place, and Navy Pier are some of the top attractions around Westchester.

Schiller Woods view in Chicago of Illinois

Check out reviews of Westchester hotels guests love

Frequently asked questions

What hotels do travelers recommend in Westchester?
Can I book a refundable hotel in Westchester?
If you need the flexibility to change your plans to Westchester, most accommodations provide refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Westchester if I want a vacation home instead of a hotel?
Browse 10 vacation homes on our site.
What will the weather in Westchester be like during my trip?
July and August are typically the warmest months in Westchester when the average temp is 71°F. January and February are the coldest months when the average temperature is 31°F. June and May are the months with the most rain.
Why should I book my Westchester hotel through Hotels.com?
There are lots of reasons to book your Westchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.