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 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

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 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.

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 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 hotel room with a large bed, a TV mounted on the wall, a desk with a chair, and a microwave.

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.

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

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

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 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.

A hotel room with a sofa, a small table, a bed, a TV, 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 building with a large glass facade, a prominent circular structure on the right, and a landscaped entrance area.

A hotel reception desk with two computer stations, a modern wall design, and a visible window.

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

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.

An outdoor patio with a wooden table and wicker chairs, surrounded by blue umbrellas, and a building with large windows in the background.

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

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

A hotel room with a green sofa, a small table with a lamp, and a refrigerator.

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

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

A hotel room with a large window, a bed, and a suitcase.

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 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.

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

Downtown Chicago

$210

$247 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 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.

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 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.

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 modern room with a flat-screen TV, a yellow sofa, a round wooden table, a patterned armchair, and a painting on the wall.

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

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

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.

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.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

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 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 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.

16. LIVN - Millennium Park Downtown Chicago

Downtown Chicago

$235

$276 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 bar area with a long counter, multiple liquor bottles, and a variety of glasses.

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 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.

A building with a marquee sign reading 'ACME HOTEL COMPANY' and a 'VACANCY' sign.

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 interior with wooden flooring, black furniture, and large windows offering city views.

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.

19. Hotel 505 River North

Downtown Chicago

$260

$341 total

includes taxes & fees

Oct 4 - Oct 5

A hotel room with a large bed, a TV, a desk, and a chair.

A modern lobby with leather sofas, a wooden coffee table, a TV mounted on the wall, and a bookshelf.

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

Congress Plaza Hotel

8/10 Good

"Nice location and nice view"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"It was clean"

River Hotel

8/10 Good

"Nice hotel; good location. Check-in staff friendly and helpful. Few minor issues: water dispenser in workout room didn’t work; hallways could be spruced up a bit."

Hilton Chicago

8/10 Good

"It was my first time in Chicago. Stay was ok. But breakfast was not included."

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."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Muy bueno todo . Excelente ubicación"

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 ."

The Royal Sonesta Chicago Downtown

10/10 Excellent

"Great"

Central Loop Hotel

10/10 Excellent

"Clean room"

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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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

Congress Plaza Hotel

InterContinental Chicago Magnificent Mile by IHG

River Hotel

Hilton Chicago

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

The Chicago Hotel Collection - Magnificent Mile

L7 Chicago by LOTTE

The Royal Sonesta Chicago Downtown

Central Loop Hotel

Frequently asked questions

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