Hotels in Westchester

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A bar area with a wooden bar counter, blue bar stools, and a variety of liquor bottles.

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.

A modern living room with a stone wall, a flat-screen TV mounted above a fireplace, and a blue armchair.

1. Four Points by Sheraton Chicago Westchester/Oak Brook

Westchester

$110

$123 total

includes taxes & fees

Oct 13 - Oct 14

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

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.

2. Carleton of Oak Park

Oak Park

$122

$136 total

includes taxes & fees

Oct 12 - Oct 13

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 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.

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

Highland Hills

$98

$108 total

includes taxes & fees

Oct 1 - Oct 2

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 reception desk with a "Welcome to the Prairie State" sign, a Hilton Honors sign, and a wooden wall with a herringbone pattern.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

4. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

$140

$161 total

includes taxes & fees

Oct 30 - Oct 31

An indoor swimming pool with clear water, surrounded by lounge chairs and tables, under a high ceiling with a grid pattern.

A hotel room with a sofa, a small table, a bed, a TV, and a painting on the wall.

A lobby with seating areas, a reception desk, and a large screen.

A hotel room with a sofa, a small wooden table, a TV, a bed, and a painting on the wall.

5. Hyatt Place Itasca

Itasca

$101

$112 total

includes taxes & fees

Oct 26 - Oct 27

A hotel room with a bed, a microwave, a refrigerator, and a coffee machine.

A modern hotel corridor with wooden paneling, a staircase, and a snack bar with various packaged goods.

A large conference room with rows of chairs, a stage, and a carpeted floor.

A modern building with a large glass facade, a prominent circular structure on the right, and a landscaped entrance area.

6. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Des Plaines

$134

$158 total

includes taxes & fees

Oct 29 - Oct 30

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

A hotel room with two beds, a desk, a chair, a TV, and a large window with a city view.

A modern living room with a sectional sofa, a fireplace, and a bar area.

A modern living room with a brown leather sofa, a coffee table, and a side table with a lamp.

7. Holiday Inn Chicago O'Hare – Rosemont by IHG

Rosemont

$134

$154 total

includes taxes & fees

Oct 25 - Oct 26

An indoor swimming pool with two separate sections, a brick wall, and a view of the outdoors through large windows.

A hotel room with two beds, each with a different patterned bedspread, a nightstand with a lamp, and a framed picture on the wall.

A spacious restaurant with multiple tables and chairs, a brick wall, and a large window.

A lobby with a brick wall, a round mirror, a glass coffee table, and a reception desk.

8. Quality Inn Schaumburg - Chicago near the Mall

Schaumburg

$97

$111 total

includes taxes & fees

Oct 25 - Oct 26

A three-tiered fruit basket on a wooden table against a wall with framed pictures.

A motel reception desk with a clock, a welcome sign, and a sign listing room types and rates.

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.

9. Heart O' Chicago

Edgewater

$105

$123 total

includes taxes & fees

Oct 1 - Oct 2

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

Downtown Chicago

$148

$176 total

includes taxes & fees

Oct 25 - Oct 26

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 hotel room with a large bed, a small dining table with chairs, a brick wall, and a window with blinds.

11. LIVN - West Loop Chicago

Downtown Chicago

$207

$243 total

includes taxes & fees

Oct 1 - Oct 2

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 lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

12. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

$179

$213 total

includes taxes & fees

Oct 25 - Oct 26

A modern rooftop lounge with white seating, a glass ceiling, and city views.

A modern building with a unique architectural design, featuring a mix of glass and concrete materials.

A rooftop bar with a city skyline view, wooden flooring, and bar stools.

A modern lounge area with seating and tables, large windows offering city views, and a high ceiling with exposed ductwork.

13. The Godfrey Hotel Chicago

Downtown Chicago

$178

$234 total

includes taxes & fees

Oct 4 - Oct 5

An indoor swimming pool with wooden beams, clear glass walls, and lounge chairs.

A hotel lobby with a dining area, a bar, and a seating area with curtains.

A hotel room with two single beds, a desk with a chair, a flat-screen TV mounted on the wall, and a window with curtains.

A hotel lobby with a marble reception desk, seating area, and a view of the outdoors.

14. Hampton Inn Chicago-Carol Stream

Carol Stream

$98

$108 total

includes taxes & fees

Oct 25 - Oct 26

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.

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.

15. Congress Plaza Hotel

Downtown Chicago

$161

$191 total

includes taxes & fees

Oct 26 - Oct 27

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.

16. LIVN - Millennium Park Downtown Chicago

Downtown Chicago

$261

$306 total

includes taxes & fees

Oct 1 - Oct 2

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 hotel room with two beds, a nightstand, a telephone, and a wall with printed text.

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

17. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

$316

$376 total

includes taxes & fees

Oct 14 - Oct 15

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.

18. ACME Hotel Chicago, Outset Collection by Hilton

Downtown Chicago

$170

$202 total

includes taxes & fees

Oct 26 - Oct 27

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

A modern high-rise building with a grid of windows and a mix of glass and concrete facades.

19. Hotel 505 River North

Downtown Chicago

$260

$341 total

includes taxes & fees

Oct 4 - Oct 5

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.

20. Central Loop Hotel

Downtown Chicago

$148

$176 total

includes taxes & fees

Oct 25 - Oct 26

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Go beyond your typical stay in Westchester

Pet friendly

Pool

Hot tub

Apart hotel

Spa

Family friendly

Our prices for hotels in Westchester are cheapest in December

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

L7 Chicago by LOTTE

10/10 Excellent

"Our favorite Chicago hotel!"

Hilton Chicago

8/10 Good

"It was a very nice place and we had an amazing time"

Eurostars Magnificent Mile

8/10 Good

"Enjoyed my stay at this hotel, it was in walking distance to mostly everything. My room was spacious and the view was amazing. I had a suite on a corner and could see straight down State Street."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent

"If I could give more than 5 stars I would. The staff was amazing and extremely accommodating and flexible. The rooms were gorgeous and the hotel was beautiful."

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"We enjoyed our stay and first visit to Chicago. All the staff were very helpful except one young lady at desk unable to help us with questions about the L train and told us to use our phones. We are an older couple 76& 80 and would have appreciated some assistance."

Hotel Saint Clair- Magnificent Mile

8/10 Good

"The room we were assigned had a wheelchair accessible bathroom which was very large took up a considerable amount of space in the room. We could barely walk around the bed, and there were no chairs nor a small desk or table. I’m not sure why we were assigned a room designed for wheelchairs, because we didn’t request any special accommodations. I’m sure they would have moved us if we had asked, but we really didn’t spend much time in the room other than to sleep. The room and bathroom were very clean and everything was working properly. The location was outstanding. We would definitely stay there again."

Fairmont Chicago at Millennium Park

10/10 Excellent

"Loved it here. Will be back again!"

River Hotel

8/10 Good

"The staff at this hotel were all very friendly and helpful. I requested extra coffee and other supplies for the room several times and they never failed to bring it to our room promptly. I did think the interior of our room was a bit outdated and could use some updating. The furniture, carpet, and bathroom all had a very old look and definitely needed updating badly. That was very minor though. Overall we enjoyed our stay very much. There were some loud motorcycles and cars every night that insisted on constantly revving their engines around 11pm-12am which was annoying. Not the fault of the property at all, but definitely something to be aware of if you’re wanting a more quiet atmosphere."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"It was clean"

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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Book Hotels in Westchester on Hotels.com

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

Where to stay in Westchester?

1. Four Points by Sheraton Chicago Westchester/Oak Brook

2. Carleton of Oak Park

3. SureStay Plus Hotel by Best Western Chicago Lombard

4. Hampton Inn Chicago-O'Hare International Airport

5. Hyatt Place Itasca

6. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

7. Holiday Inn Chicago O'Hare – Rosemont by IHG

8. Quality Inn Schaumburg - Chicago near the Mall

9. Heart O' Chicago

10. Club Quarters Hotel, Central Loop, Chicago

11. LIVN - West Loop Chicago

12. The Chicago Hotel Collection Ambassador Gold Coast

13. The Godfrey Hotel Chicago

14. Hampton Inn Chicago-Carol Stream

15. Congress Plaza Hotel

16. LIVN - Millennium Park Downtown Chicago

17. Hilton Vacation Club Hotel Blake Chicago

18. ACME Hotel Chicago, Outset Collection by Hilton

19. Hotel 505 River North

20. Central Loop Hotel

Go beyond your typical stay in Westchester

Price trends for hotels in Westchester

Typical weather for Westchester

Learn more about Westchester

Check out reviews of Westchester hotels guests love

L7 Chicago by LOTTE

Hilton Chicago

Eurostars Magnificent Mile

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Hotel Saint Clair- Magnificent Mile

Fairmont Chicago at Millennium Park

River Hotel

InterContinental Chicago Magnificent Mile by IHG

Frequently asked questions

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