Hotels in Westchester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Where to stay in Westchester?

A bar area with a wooden bar counter, blue bar stools, and a variety of liquor bottles.
A modern living room with a stone wall, a flat-screen TV mounted above a fireplace, and a blue armchair.
A modern hotel lobby with a bar area, seating arrangements, and a television screen.
A reception desk with a digital screen, name tags, and a poster advertising local favorites.

1. Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook
Westchester
$110
$123 total
includes taxes & fees
Oct 4 - Oct 5
Four Points by Sheraton Chicago Westchester/Oak Brook
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.
A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
A residential street with a sidewalk, houses, and greenery.

2. Carleton of Oak Park

Carleton of Oak Park
Oak Park
$122
$136 total
includes taxes & fees
Oct 12 - Oct 13
Carleton of Oak Park
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
A modern dining area with round tables and white chairs, a kitchen area with a coffee machine, and a view of the outdoors through large windows.
A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.

3. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
$316
$376 total
includes taxes & fees
Oct 14 - Oct 15
Hilton Vacation Club Hotel Blake Chicago
A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.
A modern conference room with a marble table, patterned chairs, a flat-screen TV, and a large window with a view of trees and parked cars.
A snack and beverage kiosk with various snacks and drinks.
A spacious lobby with a modern design, featuring a seating area with sofas and chairs, a coffee table, and a large flat-screen TV mounted on the wall.

4. SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard
Highland Hills
$98
$108 total
includes taxes & fees
Oct 1 - Oct 2
SureStay Plus Hotel by Best Western Chicago Lombard
A street view with a row of parked cars, a building with a sign reading "SONDE," and another sign that says "Diamonds On Parade."
A restaurant with outdoor seating and a sign for 'PIZANO'S PIZZA & PASTA'.
A modern kitchen with a dining area featuring two teal chairs, a round table, and a framed artwork on the wall.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a coffee maker. There is a blue sofa and a round coffee table with a striped pattern. A dining area with a table and chairs is visible in the background.

5. LIVN - Millennium Park Downtown Chicago

LIVN - Millennium Park Downtown Chicago
Downtown Chicago
$235
$276 total
includes taxes & fees
Oct 1 - Oct 2
LIVN - Millennium Park Downtown Chicago
A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view.
A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.
An indoor swimming pool with clear windows, green chairs, and a tiled deck.

6. Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
Schiller Park
$140
$161 total
includes taxes & fees
Oct 30 - Oct 31
Hampton Inn Chicago-O'Hare International Airport
A three-tiered fruit basket on a wooden table against a wall with framed pictures.
A kitchen counter with a microwave, two large containers, and baskets of bread and pastries.
A multi-story hotel with a modern design, featuring balconies with railings, large windows with curtains, and a parking area in front.
A hotel room with two beds, a large window with a city view, a painting on the wall, and a lamp on the nightstand.

7. Heart O' Chicago

Heart O' Chicago
Edgewater
$105
$123 total
includes taxes & fees
Oct 1 - Oct 2
Heart O' Chicago
A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.
A bar area with multiple shelves of bottles, a bar counter, and three bar stools.
A room with a diamond-patterned bookshelf filled with books, a wooden floor, and a lamp.
A modern living room with a brick wall mural, a green sofa, leather chairs, and a wooden coffee table.

8. Arlo Chicago

Arlo Chicago
Downtown Chicago
$202
$271 total
includes taxes & fees
Oct 25 - Oct 26
Arlo Chicago
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.
A bar with a brick archway, wooden bar counter, and stools.
A modern living room with a fireplace, leather sofas, and a wooden floor.

9. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
$148
$176 total
includes taxes & fees
Oct 25 - Oct 26
Club Quarters Hotel, Central Loop, Chicago
A spacious lobby with a central coffee table, sofas, and a large mirror.
A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.
A spacious lobby with a grand fireplace, elegant columns, and a seating area with chairs and a table.
A spacious lobby with high ceilings, large arched windows, and a grand staircase.

10. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
Downtown Chicago
$179
$213 total
includes taxes & fees
Oct 25 - Oct 26
The Chicago Hotel Collection Ambassador Gold Coast
A cozy room with a sofa, a dining table, and a window with a view of buildings.
A lobby with two brown leather chairs, a marble table, and a large potted plant.
A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.
A modern hotel lobby with a dark wood console, a large mirror, and a view of the city through large windows.

11. LIVN - West Loop Chicago

LIVN - West Loop Chicago
Downtown Chicago
$210
$247 total
includes taxes & fees
Oct 1 - Oct 2
LIVN - West Loop Chicago
A modern rooftop lounge with white seating, a glass ceiling, and city views.
A modern lounge area with seating and tables, large windows offering city views, and a high ceiling with exposed ductwork.
A modern hotel room with a cityscape view, a bed, a desk, a coffee machine, and a purple sofa.
A rooftop bar with a city skyline view, wooden flooring, and bar stools.

12. The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
Downtown Chicago
$237
$304 total
includes taxes & fees
Oct 4 - Oct 5
The Godfrey Hotel Chicago
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.
A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.
A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

13. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
$174
$207 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Chicago/Magnificent Mile Suites
A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.
A building with a marquee sign reading 'ACME HOTEL COMPANY' and a 'VACANCY' sign.
A lounge area with a checkered floor, blue sofas, a bench, and a patterned coffee table.
A modern lounge with a green sofa, armchairs, a coffee table, and a piano.

14. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
Downtown Chicago
$170
$202 total
includes taxes & fees
Oct 26 - Oct 27
ACME Hotel Chicago, Outset Collection by Hilton
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

15. The Wade

The Wade
Downtown Chicago
$149
$177 total
includes taxes & fees
Oct 25 - Oct 26
The Wade
A snack bar with various packaged snacks and beverages.
A modern hotel room with a cityscape mural, a desk with a chair, a sofa, a small table, and a lamp.
A modern hotel lobby with a large wall mural, seating area, and a digital screen displaying information.
A modern hotel lobby with a seating area, a refrigerator stocked with beverages, and a table with snacks.

16. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
Downtown Chicago
$197
$234 total
includes taxes & fees
Oct 25 - Oct 26
Cambria Hotel Chicago Loop - Theatre District
A corridor with ornate black metal railings and a patterned carpet.
A multi-story building with a grid of windows, surrounded by other high-rise buildings.
A bed with a pillow featuring a pineapple design and the text "Sleep with me." A window reveals a cityscape at night.
A modern hotel room with a sofa, a small table, a bench, a TV, and a cabinet.

17. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
$210
$279 total
includes taxes & fees
Oct 31 - Nov 1
Staypineapple, An Iconic Hotel, The Loop
A hotel bathroom with a large mirror, a sink, and a vanity.
A gym with various exercise equipment, including treadmills and weight machines.
A hotel with a classic facade, large windows, and a prominent entrance.
A bakery display with pastries and a coffee shop sign in the background.

18. Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
Downtown Chicago
$233
$306 total
includes taxes & fees
Oct 25 - Oct 26
Sports Illustrated Resorts Chicago
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A hotel room with a large bed, a TV, a desk, and a chair.
A modern living room with a fireplace, leather sofas, and a wooden floor.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.

19. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
$148
$176 total
includes taxes & fees
Oct 25 - Oct 26
Central Loop Hotel
Lobby
A spacious hotel lobby with a bar area, dining tables, and a central seating area.
A modern living room with a fireplace, leather armchairs, a sofa, and a coffee table.
A spacious lobby with a grand staircase, a large abstract painting, and a seating area with modern furniture.

20. The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
$195
$264 total
includes taxes & fees
Oct 25 - Oct 26
The Allegro Royal Sonesta Hotel Chicago Loop
View all properties
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 September
Typical weather for Westchester
September
High 24°C / low 16°C. Sunny most days.
View properties in September
24°
16°
16°
9°
9°
2°
3°
-2°
-1°
-7°
0°
-6°
7°
0°
13°
5°
19°
11°
25°
17°
27°
20°
27°
19°
Monthly weather averages (˚C)

Learn more about Westchester

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

See all hotels in Westchester
A calm lake with ducks, autumn trees, and a grassy park area.

Check out reviews of Westchester hotels guests love

Hilton Chicago

Hilton Chicago

8/10 Good
"It was my first time in Chicago. Stay was ok. But breakfast was not included."
Monica 3-night trip
Posted 4 hours ago
Hilton Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

8/10 Good
"The breakfast at Sonesta was very good! Could add more seating when when girl is full."
Carole 3-night trip
Posted 6 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Muy bueno todo . Excelente ubicación"
Julio 4-night trip
Posted 7 hours ago
The Chicago Hotel Collection - Magnificent Mile
River Hotel

River Hotel

8/10 Good
"The rooms were clean and beds were comfortable. The staff were very helpful and friendly"
Richard 2-night trip
Posted 7 hours ago
River Hotel
L7 Chicago by LOTTE

L7 Chicago by LOTTE

8/10 Good
"Nice bed in our king room. Location was perfect for us for all we had planned and coming in the CTA from midway . Disappointed no bar just the one next door at the restaurant that wasn’t open late at all . We flew in very early in morning hoped to get into a room early even if we had to pay extra but the check in person was no help at all in regards to check in early or any of our questions . Our family came in the next morning same time and this time a different check in person actually offered them to check in early ! We had nowhere to go so we walked a lot of the city waiting to check in . I think we walked 13 miles . Our room ,once we got it ,was nice tho we didn’t get the city view just the view across to a building and parking . Location was definitely the highlight of this hotel ."
sandra 2-night trip
Posted 7 hours ago
L7 Chicago by LOTTE
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Great"
justin 3-night trip
Posted 7 hours ago
The Royal Sonesta Chicago Downtown
Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"Clean room"
Gordon 1-night trip
Posted 8 hours ago
Central Loop Hotel
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

10/10 Excellent
"Traveling cross country and stayed at several hotel. This one was on point, from entering the hotel, smelling clean, the staff checking in was great, and the room was clean. I had an awesome stay."
Jose 2-night trip
Posted 12 hours ago
Hampton Inn Chicago Downtown/Magnificent Mile
The Wade

The Wade

10/10 Excellent
"Everything great and everyone e great"
Holly 4-night trip
Posted 13 hours ago
The Wade

Frequently asked questions

What hotels do travelers recommend in Westchester?
Guests like 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 5 vacation homes on our site. In addition, you can choose from 5 apartments.
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.

Keep exploring