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Westchester Vacation Packages
Save Time and Money with a Westchester Package Deal
Booking your flights and accommodation is easy with Expedia. You'll save your money and time simply by combining your lodging and flight bookings with us. See more on your Westchester trip with the extra cash.
Book your package deal today and get savings up to C$590!
Select from some 400 partner airlines and 321,000 worldwide hotels via our international catalogue of flights and lodgings.
Think of the money you'll save with some of the top prices and deals via Expedia.
You can postpone your vacation itineraries with us because we don't 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.
Accommodation in Westchester
Before you leave, get a reservation for one of the 37 Westchester accommodation options that can be found on Expedia's hotel booking platform.
The Hyatt Lodge at McDonald's Campus, located at 2815 Jorie Blvd, and the Le Méridien Chicago - Oakbrook Center, at 2100 Spring Road, are great examples of upscale hotels in Westchester. Alternatively, the American Inn & Suites, at 6401 Joliet Rd, and the Extended Stay America - Chicago - Elmhurst - O'Hare, at 550 W Grand Ave, are two more economical choices worth looking into.
Top Hotel Deals
Hampton Inn Chicago/Westchester (Oak Brook)
2222 Enterprise Drive, WestchesterSituated in the business district, this hotel is within 3 mi (5 km) of Oak Brook Golf Course, Oakbrook Center Mall, and Drury Lane Theater. Brookfield Zoo and Stevenson Park are also within 6 mi (10 km).
Congress Plaza Hotel
520 South Michigan Avenue, ChicagoBuilt in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.
Warwick Allerton - Chicago
701 North Michigan Avenue, ChicagoLocated 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.
River Hotel
75 East Wacker Drive, ChicagoLocated in The Loop, this hotel is steps from Downtown Chicago and Chicago Riverwalk.
Club Quarters Hotel, Central Loop
111 West Adams Street, ChicagoClub Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board of Trade, Willis Tower, Grant Park and the Riverfront, the Theatre District and Magnificent Mile.
Kimpton Hotel Allegro
171 W Randolph St, ChicagoLocated in the Loop's theater district, Kimpton Hotel Allegro is next to the Cadillac Palace Theatre, 4 blocks from Millennium Park, and 1 mile from the Magnificent Mile.
Hyatt Regency Chicago
151 East Wacker Dr, ChicagoThis Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are less than a mile away.
Best Western Grant Park Hotel
1100 S Michigan Ave, ChicagoFavored for its location across from Grant Park, Museum Campus, Soldier Field, and Northerly Island, the Best Western Grant Park is also 1 mile from Millennium Park and Chicago's theater district.
Top Flight + Hotel Deals
Hilton Chicago O'Hare Airport
4.0 out of 5.0Mon, 30 Jul - Fri, 3 Aug
Jean Lesage Intl. - O'Hare Intl.
C$1,508 per person
Hotel Lincoln
4.0 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$2,186 per person
Conrad Chicago
4.5 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$2,087 per person
Marriott Marquis Chicago
4.0 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$1,591 per person
Holiday Inn Express & Suites Chicago North Shore - Niles
2.5 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$1,093 per person
Thompson Chicago
4.5 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$1,724 per person
Hilton Garden Inn Lake Forest Mettawa
3.0 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$1,249 per person
Holiday Inn Chicago North Shore
3.0 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$1,033 per person
Fairmont Chicago at Millennium Park
4.5 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$2,103 per person
Hilton Rosemont Chicago O'Hare
3.5 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$1,285 per person
Sheraton Suites Chicago O'Hare
3.5 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$1,205 per person
Kimpton Gray Hotel
4.5 out of 5.0Thu, 2 Aug - Thu, 9 Aug
Pierre Elliott Trudeau Intl. - O'Hare Intl.
C$2,155 per person
Top Deals On Flights
These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.
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