Hotels in Westchester

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Check prices for these dates

Tonight
Apr 27 - Apr 28
Tomorrow
Apr 28 - Apr 29
This weekend
May 1 - May 3
Next weekend
May 8 - May 10

Where to stay in Westchester?

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, (1,003 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 $101
$113 total
includes taxes & fees
May 10 - May 11
Four Points by Sheraton Chicago Westchester/Oak Brook
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,473 reviews)
Experience the unique charm of this waterfront hotel with panoramic Lake Michigan vistas. Just steps from Navy Pier, enjoy Latin American cuisine at Lirica or unwind at one of 2 bars. A 24-hour fitness center and convenient access to Michigan Avenue complete your Chicago adventure.
The price is $190
$260 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton
Indoor wedding
Swissotel - Chicago
Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,284 reviews)
Experience Chicago's finest at this luxury hotel near Michigan Avenue and Millennium Park. Enjoy deep-tissue massages or dine at The Palm restaurant with 24-hour room service. Just minutes from Chicago Riverwalk and convenient public transit stations.
The price is $198
$271 total
includes taxes & fees
May 27 - May 28
Swissotel - Chicago
Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,445 reviews)
Immerse in urban charm at this hotel with a refreshing rooftop pool and terrace overlooking the cityscape. Just steps from Michigan Avenue shopping and Chicago Riverwalk, with Grand Station only 9 minutes away.
The price is $152
$181 total
includes taxes & fees
May 10 - May 11
DoubleTree by Hilton Chicago - Magnificent Mile
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, (2,830 reviews)
Immerse in Chicago's bustling energy at this business-friendly hotel near Michigan Avenue and Chicago Riverwalk. Fuel up with free breakfast before exploring or working out at the fitness center. Grand Station is just 8 minutes away for easy city adventures.
The price is $142
$198 total
includes taxes & fees
May 10 - May 11
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lunch and dinner served
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,930 reviews)
Immerse yourself in downtown Chicago at this luxurious hotel with seasonal outdoor and indoor pools. Just minutes from the Chicago Riverwalk and Millennium Park, enjoy FireLake restaurant, a 24-hour fitness center, and bar/lounge after exploring the city.
The price is $202
$266 total
includes taxes & fees
May 25 - May 26
Radisson Blu Aqua Hotel Chicago
Executive lounge
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,139 reviews)
Tucked in downtown Chicago, this hotel offers a full-service spa and American cuisine at Lobby Bar. Just a 5-minute walk to Millennium Park and Michigan Avenue, with 2 bars/lounges and a 24-hour fitness center nearby.
The price is $172
$240 total
includes taxes & fees
May 8 - May 9
Fairmont Chicago at Millennium Park
Lobby
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,213 reviews)
Discover urban bliss at this Chicago hotel with an indoor pool and American cuisine restaurant. Near Michigan Avenue and Riverwalk, with Grand Station just 9 minutes away. Guests love the comfortable beds, helpful staff, and prime location.
The price is $121
$142 total
includes taxes & fees
Apr 28 - Apr 29
Aloft Chicago Mag Mile
Bar (on property)
Ivy Boutique Hotel
Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,242 reviews)
The price is $152
$178 total
includes taxes & fees
May 26 - May 27
Ivy Boutique Hotel
Lobby
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,447 reviews)
The price is $139
$166 total
includes taxes & fees
May 10 - May 11
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,008 reviews)
Set in the heart of downtown, this hotel is a 10-minute walk to Michigan Avenue and Chicago Riverwalk. Guests praise the helpful staff and complimentary continental breakfast. With free WiFi and a fitness center, you're just 8 minutes from Grand Station Red Line.
The price is $119
$140 total
includes taxes & fees
Apr 28 - Apr 29
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Exterior
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,214 reviews)
The price is $139
$165 total
includes taxes & fees
May 10 - May 11
Hilton Chicago/Magnificent Mile Suites
Shopping mall
Millennium Hotel Knickerbocker Chicago
Millennium Hotel Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,963 reviews)
This iconic 1920s hotel sits steps from Water Tower Place and Lake Michigan, with Chicago's Red Line 10 minutes away. Enjoy comfortable beds, a 24-hour fitness center, and NiX Restaurant serving fresh morning fare amid historic elegance.
The price is $116
$164 total
includes taxes & fees
May 10 - May 11
Millennium Hotel Knickerbocker Chicago
Exterior
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,495 reviews)
Perfectly positioned near Michigan Avenue and Chicago Riverwalk, this hotel offers breathtaking city and Lake Michigan views. With 4 restaurants, including Stetsons Modern Steak, plus 2 bars, you'll enjoy comfort while staying steps from shopping and attractions.
The price is $212
$288 total
includes taxes & fees
May 25 - May 26
Hyatt Regency Chicago
Exterior
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,092 reviews)
The price is $152
$210 total
includes taxes & fees
May 10 - May 11
Hyatt Centric Chicago Magnificent Mile
Premium bedding, in-room safe, desk, blackout drapes
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,870 reviews)
The price is $165
$199 total
includes taxes & fees
May 10 - May 11
Courtyard by Marriott Chicago Magnificent Mile
Exterior
The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (1,343 reviews)
Immerse in Chicago's vibrant energy at this boutique hotel. Steps from Michigan Avenue and Water Tower Place, enjoy clean rooms with city vistas. Grab breakfast at the Lobby Bar before exploring nearby Lake Michigan and Chicago Riverwalk.
The price is $104
$122 total
includes taxes & fees
Apr 29 - Apr 30
The Chicago Hotel Collection - Magnificent Mile
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,977 reviews)
The price is $140
$194 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago
Lobby
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (10,151 reviews)
This historic hotel offers majestic lake views and is steps from Columbia College Chicago. Enjoy meals at 2 restaurants or the café, then unwind at the bars. With train stations nearby and helpful staff, you'll experience both charm and convenience.
The price is $124
$147 total
includes taxes & fees
May 8 - May 9
Congress Plaza Hotel
Restaurant
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (2,682 reviews)
The price is $116
$138 total
includes taxes & fees
May 26 - May 27
Best Western Grant Park Hotel
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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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 April
Currently viewing crowd sizes and weather for April.
Typical weather for Westchester
April
High 13°C / low 5°C. Partly sunny.
View properties in April
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April, no crowd data, average high temperature 13 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
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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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Monthly weather averages (˚C)

Learn more about Westchester

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

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

Check out reviews of Westchester hotels guests love

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"I have gone by this hotel for over thirty years and always wanted to stay here. Our room had a magnificent view of the lake and everything from the Ferris wheel at Navy Pier to the Field Museum. The room did not have good climate control. We did have to have the windows open. Thankfully, the weather was mild outside, which made things ultimately very comfortable."
Kipp 2-night trip
Posted less than an hour ago
Congress Plaza Hotel

Frequently asked questions

What hotels do travelers recommend in Westchester?
Guests like Hilton Chicago O'Hare Airport and Hyatt Regency O'Hare Chicago.
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.