Hotels in Westchester

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Check prices for these dates

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
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 reception desk with a digital screen, name tags, and a poster advertising local favorites.
A modern hotel lobby with a bar area, seating arrangements, and a television screen.
A hotel room with a large bed, a desk, a chair, a wardrobe, and a view of the city through a large window.

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 lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.
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
Sep 30 - Oct 1
Carleton of Oak Park
A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.
A snack and beverage kiosk with various snacks and drinks.
A hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.
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.

3. SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard
Highland Hills
$93
$104 total
includes taxes & fees
Sep 30 - Oct 1
SureStay Plus Hotel by Best Western Chicago Lombard
A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.
An indoor swimming pool with clear windows, green chairs, and a tiled deck.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view.
A reception desk with a "Welcome to the Prairie State" sign, a Hilton Honors sign, and a wooden wall with a herringbone pattern.

4. 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 building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A bar with a brick archway, wooden bar counter, and stools.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.
A modern living room with a fireplace, leather sofas, and a wooden floor.

5. 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 three-tiered fruit basket on a wooden table against a wall with framed pictures.
A hotel room with two beds, a large window with a city view, a painting on the wall, and a lamp on the nightstand.
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.

6. Heart O' Chicago

Heart O' Chicago
Edgewater
$105
$123 total
includes taxes & fees
Oct 1 - Oct 2
Heart O' Chicago
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 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.
A modern kitchen with a dining area featuring two teal chairs, a round table, and a framed artwork on the wall.
A restaurant with outdoor seating and a sign for 'PIZANO'S PIZZA & PASTA'.

7. LIVN - Millennium Park Downtown Chicago

LIVN - Millennium Park Downtown Chicago
Downtown Chicago
$214
$251 total
includes taxes & fees
Oct 1 - Oct 2
LIVN - Millennium Park Downtown Chicago
A spacious lobby with a central coffee table, sofas, and a large mirror.
A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.
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 high ceilings, large arched windows, and a grand staircase.

8. 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 restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.
A high-rise building with a modern architectural design, featuring a prominent glass facade and a series of vertical lines.
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.

9. Arlo Chicago

Arlo Chicago
Downtown Chicago
$202
$271 total
includes taxes & fees
Oct 25 - Oct 26
Arlo Chicago
A cityscape at dusk with high-rise buildings, including a Hilton hotel.
A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.
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.

10. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
$175
$208 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 hotel room with a bed, desk, lamp, and a wall with a handprint design.
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.

11. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
Downtown Chicago
$165
$196 total
includes taxes & fees
Oct 26 - Oct 27
ACME Hotel Chicago, Outset Collection by Hilton
A cozy room with a sofa, a dining table, 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.
A hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.
A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.

12. LIVN - West Loop Chicago

LIVN - West Loop Chicago
Downtown Chicago
$217
$255 total
includes taxes & fees
Oct 1 - Oct 2
LIVN - West Loop Chicago
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.
A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

13. The Wade

The Wade
Downtown Chicago
$149
$177 total
includes taxes & fees
Oct 25 - Oct 26
The Wade
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.

14. 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 building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.
A person sitting on a couch with a laptop, reading a book, in a room with a large window and a framed picture on the wall.
A modern living room with a fireplace, leather sofas, and a wooden floor.

15. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
$148
$176 total
includes taxes & fees
Oct 25 - Oct 26
Central Loop Hotel
A modern rooftop lounge with white seating, a glass ceiling, and city views.
A rooftop bar with a city skyline view, wooden flooring, and bar stools.
A modern hotel room with a cityscape view, a bed, a desk, a coffee machine, and a purple sofa.
A modern lounge area with seating and tables, large windows offering city views, and a high ceiling with exposed ductwork.

16. 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 spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

17. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
$161
$191 total
includes taxes & fees
Oct 26 - Oct 27
Congress Plaza Hotel
A building with a stone facade and large glass windows.
A hotel room with a large bed, two bedside tables with lamps, a chair, and a city view through large windows.
A room with a white wardrobe, a grey sofa, and a mirror on the wall.
A room with a large window, a patterned armchair, and a view of a cityscape with buildings and a street.

18. Ohio House Motel

Ohio House Motel
Downtown Chicago
$167
$196 total
includes taxes & fees
Oct 25 - Oct 26
Ohio House Motel
A hotel bathroom with a large mirror, a sink, and a vanity.
A bakery display with pastries and a coffee shop sign in the background.
A hotel with a classic facade, large windows, and a prominent entrance.
A hotel room with a view of a cityscape through a large window, a floor lamp, a sofa with cushions, and a small table with a plant.

19. 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 large, historic building with a central courtyard surrounded by trees.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

20. Hilton Chicago

Hilton Chicago
Downtown Chicago
$166
$226 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Chicago
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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

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Excelente relación precio calidad"
Andres 1-night trip
Posted 1 hour ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"I had a wonderful stay at the Central Loop Hotel. The hotel offered the option of a fully automated check-in, which was very convenient, while staff were also readily available and consistently friendly and helpful. My room was clean and quiet and had everything I needed, including a Nespresso machine. After checkout, the hotel stored my bags for several hours so I could spend more time exploring Chicago before my train. The location was excellent…an easy walk from Union Station and very convenient for seeing the city. There is also a very popular restaurant accessible directly through the hotel lobby. I would happily stay here again, particularly when traveling by train. The combination of location, comfort, and helpful staff made for a very easy and enjoyable stay."
Elizabeth 1-night trip
Posted 1 hour ago
Central Loop Hotel
Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"Unable to adjust temperature control in room. Only a low, medium and high! Other than this, no complaints. Very convenient for Bears game."
Todd 1-night trip
Posted 2 hours ago
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

10/10 Excellent
"Very good stay the hotel was clean and the bed was comfortable, close to all the good spots as well. I’d stay here again in the future"
Gordon 2-night trip
Posted 2 hours ago
Hilton Chicago
Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"I didn’t like the bathroom doors & the windows you can hear everything"
James 3-night trip
Posted 2 hours ago
Eurostars Magnificent Mile
L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Excellent location, excellent staff, happy hour drinks were very good. Room was clean and quiet"
Greg 2-night trip
Posted 3 hours ago
L7 Chicago by LOTTE
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 3 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 4 hours ago
The Wade
River Hotel

River Hotel

8/10 Good
"."
Tracie 2-night trip
Posted 20 hours ago
River Hotel

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.

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