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 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

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 residential street with a sidewalk, houses, and greenery.

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

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 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.

A snack and beverage kiosk with various snacks and drinks.

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 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.

4. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

$140

$161 total

includes taxes & fees

Oct 30 - Oct 31

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 modern living room with a fireplace, leather sofas, and a wooden floor.

A restaurant interior with brick walls, wooden tables and chairs, and a bar area.

5. Club Quarters Hotel, Central Loop, Chicago

Downtown Chicago

$148

$176 total

includes taxes & fees

Oct 25 - Oct 26

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

A hotel room with two beds, a large window with a city view, a painting on the wall, and a lamp on the nightstand.

6. Heart O' Chicago

Edgewater

$105

$123 total

includes taxes & fees

Oct 1 - Oct 2

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.

7. 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 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.

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

8. The Godfrey Hotel Chicago

Downtown Chicago

$178

$234 total

includes taxes & fees

Oct 4 - Oct 5

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 modern lounge with a green sofa, armchairs, a coffee table, and a piano.

A lounge area with a checkered floor, blue sofas, a bench, and a patterned coffee table.

9. ACME Hotel Chicago, Outset Collection by Hilton

Downtown Chicago

$170

$202 total

includes taxes & fees

Oct 26 - Oct 27

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

A hotel room with a sofa, armchair, a flat-screen TV, a bed, and a view of the city and ocean.

A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

10. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

$174

$207 total

includes taxes & fees

Oct 25 - Oct 26

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

A bar area with a long counter, multiple liquor bottles, and a variety of glasses.

11. Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

$316

$376 total

includes taxes & fees

Oct 14 - Oct 15

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 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

Downtown Chicago

$207

$243 total

includes taxes & fees

Oct 1 - Oct 2

A restaurant interior with brick walls, hanging spherical light fixtures, and a visible kitchen area.

A modern living room with a brick wall mural, a green sofa, leather chairs, and a wooden coffee table.

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.

13. Arlo Chicago

Downtown Chicago

$202

$271 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

14. The Wade

Downtown Chicago

$149

$177 total

includes taxes & fees

Oct 25 - Oct 26

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.

15. Central Loop Hotel

Downtown Chicago

$148

$176 total

includes taxes & fees

Oct 25 - Oct 26

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 grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.

16. Congress Plaza Hotel

Downtown Chicago

$161

$191 total

includes taxes & fees

Oct 26 - Oct 27

A hotel bathroom with a large mirror, a sink, and a vanity.

A gym with various exercise equipment, including treadmills and weight machines.

A bakery display with pastries and a coffee shop sign in the background.

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.

17. Sports Illustrated Resorts Chicago

Downtown Chicago

$233

$306 total

includes taxes & fees

Oct 25 - Oct 26

A bar area with a long counter, bar stools, and a mirrored wall.

A restaurant with wooden flooring, long tables, and chairs with patterned upholstery.

A luxurious bathroom with a large oval bathtub, a chandelier, and two large mirrors with floral arrangements.

A luxurious lobby with a grand fireplace, elegant seating arrangements, and classic wood paneling.

18. The Whitehall Hotel, BW Premier Collection

Downtown Chicago

$169

$201 total

includes taxes & fees

Oct 26 - Oct 27

A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

A laundry area with a washing machine, a dryer, and an ice dispenser.

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 modern interior with a dining area, sofas, and artwork on the walls.

19. Hotel Saint Clair- Magnificent Mile

Downtown Chicago

$169

$204 total

includes taxes & fees

Oct 1 - Oct 2

A large, historic building with a central courtyard surrounded by trees.

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.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

20. Hilton Chicago

Downtown Chicago

$166

$227 total

includes taxes & fees

Oct 30 - Oct 31

View all properties

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

River Hotel

10/10 Excellent

"Excellent stay at the River Hotel in Chicago! The location is absolutely perfect—right on the river and within walking distance of many of the city’s best attractions. The room was clean, comfortable, and had everything we needed. The staff was friendly, welcoming, and always helpful. Great value for such a fantastic downtown location—we would definitely stay here again!"

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent

"We only stayed for a night but it was in a Great location and the staff and room was excellent. Would definitely stay again."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"They let us in before 4pm. Very accommodating and respectful all the staff. Location is best."

L7 Chicago by LOTTE

10/10 Excellent

"Alex was amazing at check in! Great experience!"

Congress Plaza Hotel

8/10 Good

"A great value for the money. An awesome location across from Lake Michigan and the Grant Park fountain. The lobby is wonderful, but the room and the rest of it looks very aged with layers of paint and forgone maintenance."

Hilton Chicago

10/10 Excellent

"Easy check in/check out, easy and available parking, Friendly and helpful staff, clean and updated room"

Hotel Saint Clair- Magnificent Mile

8/10 Good

"The room was really oddly laid out (It's an older building), but everything looked and felt nice. It has a nice modern look to everything, and the water was really hot which is rare for most hotels, especially in Chicago in my experience. The location is absolutely fantastic for downtown shopping, parks, pier, food. Two minute walk to the heart of the Magnificent Mile. There was a fridge, microwave, and coffee machine in the room. We stocked up on fresh pastries from a fantastic bakey a few stores down, and went to the 7-Eleven on the corner for drinks for late night snacks. I've stayed at maybe 10 different hotels in this class in Chicago and I think this is one of the better ones. For parking, just an app and save some(A LOT) money. Lots of garages nearby that discount heavily with apps."

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."

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."

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. Club Quarters Hotel, Central Loop, Chicago

6. Heart O' Chicago

7. The Chicago Hotel Collection Ambassador Gold Coast

8. The Godfrey Hotel Chicago

9. ACME Hotel Chicago, Outset Collection by Hilton

10. Hilton Chicago/Magnificent Mile Suites

11. Hilton Vacation Club Hotel Blake Chicago

12. LIVN - West Loop Chicago

13. Arlo Chicago

14. The Wade

15. Central Loop Hotel

16. Congress Plaza Hotel

17. Sports Illustrated Resorts Chicago

18. The Whitehall Hotel, BW Premier Collection

19. Hotel Saint Clair- Magnificent Mile

20. Hilton Chicago

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

River Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

The Chicago Hotel Collection Ambassador Gold Coast

L7 Chicago by LOTTE

Congress Plaza Hotel

Hilton Chicago

Hotel Saint Clair- Magnificent Mile

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Hampton Inn Chicago Downtown/Magnificent Mile

Frequently asked questions

Keep exploring