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 modern living room with a stone wall, a flat-screen TV mounted above a fireplace, and a blue armchair.
A hotel room with a large bed, a desk, a chair, a wardrobe, and a view of the city through a large window.
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 lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.
A residential street with a sidewalk, houses, and greenery.
A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

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 modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.
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.
A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

3. Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
Schiller Park
$140
$161 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Chicago-O'Hare International Airport
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 hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.
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
$93
$104 total
includes taxes & fees
Sep 30 - Oct 1
SureStay Plus Hotel by Best Western Chicago Lombard
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
A reception area with a desk, a seating area with a blue sofa, and a bookshelf filled with books.
Front of property
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

5. 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 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 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.

6. 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 spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.
A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

7. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
$161
$191 total
includes taxes & fees
Oct 26 - Oct 27
Congress Plaza Hotel
A three-tiered fruit basket on a wooden table against a wall with framed pictures.
A multi-story hotel with a modern design, featuring balconies with railings, large windows with curtains, and a parking area in front.
A kitchen counter with a microwave, two large containers, and baskets of bread and pastries.
A hotel room with two beds, a large window with a city view, a painting on the wall, and a lamp on the nightstand.

8. Heart O' Chicago

Heart O' Chicago
Edgewater
$105
$123 total
includes taxes & fees
Oct 1 - Oct 2
Heart O' Chicago
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 rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.

9. The Wade

The Wade
Downtown Chicago
$149
$177 total
includes taxes & fees
Oct 25 - Oct 26
The Wade
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 modern living room with a fireplace, leather sofas, and a wooden floor.
A bar with a brick archway, wooden bar counter, and stools.

10. 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 cozy room with a sofa, a dining table, and a window with a view of buildings.
A cozy seating area with a round table and two chairs, a brick wall, and a window with a view of buildings.
A lobby with two brown leather chairs, a marble table, and a large potted plant.
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
$217
$255 total
includes taxes & fees
Oct 1 - Oct 2
LIVN - West Loop Chicago
A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.
A person sitting on a blue couch with a dog beside them, holding a glass of wine, and a pizza on a wooden board on a table.
A hotel room with two beds, a window with curtains, a bedside table with a lamp, and a small ottoman.
A laundry area with a washing machine, a dryer, and an ice dispenser.

12. Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$169
$204 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Saint Clair- Magnificent Mile
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 hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

13. Hilton Chicago

Hilton Chicago
Downtown Chicago
$166
$227 total
includes taxes & fees
Oct 30 - Oct 31
Hilton 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 neatly arranged hotel room with a large bed, a nightstand, a lamp, and a window with a view of buildings.
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.

14. 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
An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.
A window with a view of a cityscape, a wooden desk with a radio, and a small window ledge.
A spacious indoor area with seating arrangements, large windows, and indoor plants.
A modern lobby with a sofa, coffee table, and potted plants.

15. The Emily Hotel

The Emily Hotel
Downtown Chicago
$281
$334 total
includes taxes & fees
Oct 4 - Oct 5
The Emily 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 hotel with a classic facade, multiple flags, and a prominent entrance.

16. The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
$190
$258 total
includes taxes & fees
Oct 25 - Oct 26
The Allegro Royal Sonesta Hotel Chicago Loop
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 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.

17. Arlo Chicago

Arlo Chicago
Downtown Chicago
$202
$271 total
includes taxes & fees
Oct 25 - Oct 26
Arlo Chicago
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.
A rooftop pool area with lounge chairs and a view of the city skyline.
A bar with multiple shelves of bottles, a long counter, and several stools.
A spacious lobby with a fireplace, comfortable seating, and a modern chandelier.

18. The Hoxton, Chicago

The Hoxton, Chicago
Downtown Chicago
$329
$421 total
includes taxes & fees
Oct 4 - Oct 5
The Hoxton, Chicago
Lobby
A modern hotel lobby with grey upholstered chairs, a wooden coffee table, and a large window offering a view of the city and an American flag.
A hotel room with a large window, a bed, a desk, a chair, and a lamp.
A tall, modern hotel with a brick facade and numerous windows.

19. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Downtown Chicago
$176
$209 total
includes taxes & fees
Oct 27 - Oct 28
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
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 hotel room with a large bed, a TV, a desk, and a chair.

20. Central Loop Hotel

Central Loop Hotel
Downtown Chicago
$148
$176 total
includes taxes & fees
Oct 25 - Oct 26
Central Loop Hotel
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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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Always a great option!"
Robin 4-night trip
Posted less than an hour ago
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

10/10 Excellent
"It was good..."
Michael 1-night trip
Posted 5 hours ago
Hilton Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"Comfortable, clean full apartment! Meant for extended stay but we were there only for the night. Great surprise!"
kathleen 1-night trip
Posted 5 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"The hotel is on the very busy side of the river on Wacker Drive. There's definitely more noise and the parking is not convenient at all unless you valet park. Also beware of booking rooms on the 38th floor because there's ballroom on the 39th floor and when the music is playing you can hear it all in the room."
Ben 4-night trip
Posted 6 hours ago
The Royal Sonesta Chicago Downtown
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Great Hotel! I would definitely recommend."
Lisa 1-night trip
Posted 8 hours ago
Hyatt Regency O'Hare Chicago
River Hotel

River Hotel

8/10 Good
"."
Tracie 2-night trip
Posted 10 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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