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Westchester Vacation Packages

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 C$590.

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.

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

See all 747 Hotels in Westchester
C$94
Hampton Inn Chicago/Westchester (Oak Brook)

Hampton Inn Chicago/Westchester (Oak Brook)

2222 Enterprise Drive, Westchester
4.3
of 5, from 665 reviews
3.0 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.

C$148
Hyatt Regency Chicago

Hyatt Regency Chicago

151 East Wacker Dr, Chicago
4.4
of 5, from 8,910 reviews
4.5 out of 5.0

This 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.

C$99
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.2
of 5, from 9,733 reviews
4.5 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.

C$105
Kinzie Hotel

Kinzie Hotel

20 W Kinzie St, Chicago
4.5
of 5, from 3,890 reviews
4.5 out of 5.0

Within 2 blocks of Chicago's Magnificent Mile and the theater district, the Kinzie Hotel is located in the convenient River North district, a mile from the Hancock Tower and Lake Michigan.

C$85
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.6
of 5, from 1,760 reviews
3.5 out of 5.0

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

C$81
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
4.1
of 5, from 7,331 reviews
4.5 out of 5.0

Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

C$94
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

163 East Walton Place, Chicago
4.3
of 5, from 5,486 reviews
4.5 out of 5.0

This 1927 landmark Chicago hotel is a half block from Michigan Avenue/Magnificent Mile shopping, two blocks from Oak Street shopping and Water Tower Place. Lake Michigan is three blocks away.

C$91
Club Quarters Hotel, Central Loop

Club Quarters Hotel, Central Loop

111 West Adams Street, Chicago
4.3
of 5, from 5,927 reviews
4.5 out of 5.0

Club 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.

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