Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Save up to $603 by booking Flight + Hotel.

Search 321,000 hotels and 400 airlines worldwide.

Get the price Guarantee available for your trip.


Westchester is a suburb in Chicago, a marvelous city that is home to 2,700,000 people.

Packages in Westchester

Save cash with your Expedia package deal. When you bundle your flight and accommodation bookings together into one easy package, you save money. Experience more on your Westchester trip with the extra money.

Vacationers who take full advantage of package deals can save as much as $603.

With our database of some 400 partner airlines and 321,000 hotels, how can you ever go wrong?

Browse the great deals at Expedia and book that special trip you've been thinking about. Your family will thank you for it.

You can postpone your travel reservations with us because we do not charge cancellation fees for almost all of our bookings.

Westchester Vacation Packages

If you're flying in via O'Hare International Airport, head 9 miles south to get to Westchester. Then, when it's time to head for the city, it'll be just 14 miles away.

There's loads to experience nearby! You must visit Ernest Hemingway Museum and House and Unity Temple. Most locals also recommend Frank Lloyd Wright Home and Studio and Madison Street Theatre. Another idea is to head over to a neighboring area, such as Hillside or La Grange Park.

University of Chicago is an iconic sight that has to be on your agenda. It is about 6 miles from the heart of the city.

Adler Planetarium and Astronomy Museum and Chicago Children's Museum are just a couple of the memorable choices that are waiting for you in this vibrant city. You can also check out Navy Pier and John G. Shedd Aquarium.

On the hunt for something to do on a rainy day? Graue Mill and Museum and Lizzadro Museum of Lapidary Art have a mix of interesting exhibits.

Do you think you've got what it takes to score a few birdies at Oak Brook Golf Course and Fresh Meadow Golf Club? These much-loved courses give even the most experienced pros a serious run for their money.

Take a break in the sunshine at one of the local parklands, such as Stevenson Park, York Woods County Forest Preserve and Park District of La Grange.

You never know what truths you may uncover at Forest Home Cemetery and Mayslake Peabody Mansion. These time-weathered sites have their fair share of stories to tell.

Booking a great place to stay is a crucial part of any vacation. Expedia gives easy access to some of the nicest Westchester lodgings.

The Hyatt Lodge at McDonald's Campus at 2815 Jorie Blvd, and the Le Méridien Chicago - Oakbrook Center, at 2100 Spring Road are two excellent examples of the better quality hotels in Westchester. If you want to see what the cheaper options are like, the American Inn & Suites, at 6401 Joliet Rd, and the Extended Stay America - Chicago - Elmhurst - O'Hare, at 550 W Grand Ave, are worth considering also.

Top Hotel Deals

See all 681 Hotels in Westchester
Hampton Inn Chicago/Westchester (Oak Brook)

Hampton Inn Chicago/Westchester (Oak Brook)

2222 Enterprise Drive, Westchester
of 5, from 154 reviews
2.5 out of 5.0

Situated in the business district, this hotel is within 3 mi (5 km) of Oak Brook Golf Course, York Woods County Forest Preserve, and Oakbrook Center Mall. Drury Lane Theater is 3 mi (4.9 km) away.

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
of 5, from 456 reviews
3.0 out of 5.0

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

IHSP Chicago Hostel

IHSP Chicago Hostel

1616 North Damen Avenue, Chicago
of 5, from 8 reviews
2.0 out of 5.0

Located in West Town, this hostel is within 3 mi (5 km) of Humboldt Park, United Center, and Merchandise Mart. Lincoln Park Zoo is 3 mi (4.9 km) away.

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
of 5, from 2,579 reviews
4.0 out of 5.0

This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent Mile shopping, and Wrigley Tower.

Inn of Chicago

Inn of Chicago

162 E Ohio St, Chicago
of 5, from 1,935 reviews
3.0 out of 5.0

Inn of Chicago is a half-block from the Magnificent Mile and 2 blocks from the landmark Tribune Tower. Millennium Park, Navy Pier, and the Art Institute of Chicago are among the many attractions within 1 mile.

Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
of 5, from 2,542 reviews
4.0 out of 5.0

Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from Lake Michigan and the Art Institute.

Hard Rock Hotel Chicago

Hard Rock Hotel Chicago

230 North Michigan Avenue, Chicago
of 5, from 2,095 reviews
4.0 out of 5.0

On Michigan Avenue and across from Millennium Park, this rock-inspired hotel occupies the 36-story, Art Deco-style Carbide and Carbon Building in downtown's Loop; Macy's is a block away.

Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
of 5, from 1,373 reviews
3.5 out of 5.0

Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, and a mile from Loop theaters.

Top Flight + Hotel Deals

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.