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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 792 Hotels in Westchester
Hampton Inn Chicago/Westchester (Oak Brook) C$93
Hampton Inn Chicago/Westchester (Oak Brook)

Hampton Inn Chicago/Westchester (Oak Brook)

2222 Enterprise Drive, Westchester
    of 5, from 686 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.

    Central Loop Hotel C$126
    Central Loop Hotel

    Central Loop Hotel

    111 West Adams Street, Chicago
      of 5, from 4,028 reviews
      4.0 out of 5.0

      Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago Board of Trade, Chicago Mercantile Exchange, Grant Park, the State Street shopping district and the Art Institute of Chicago.

      River Hotel C$129
      River Hotel

      River Hotel

      75 East Wacker Drive, Chicago
        of 5, from 4,183 reviews
        4.0 out of 5.0

        Located in The Loop, this hotel is within a 10-minute walk of Chicago Theatre, Wrigley Building, and Tribune Tower. Ford Center for the Performing Arts Oriental Theatre and Chicago Cultural Center are also within 10 minutes.

        The Whitehall Hotel C$132
        The Whitehall Hotel

        The Whitehall Hotel

        105 E Delaware Pl, Chicago
          of 5, from 7,563 reviews
          4.0 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.

          Wyndham Grand Chicago Riverfront C$141
          Wyndham Grand Chicago Riverfront

          Wyndham Grand Chicago Riverfront

          71 E Wacker Dr, Chicago
            of 5, from 6,523 reviews
            4.0 out of 5.0

            This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago.

            Edward Hotel Chicago C$134
            Edward Hotel Chicago

            Edward Hotel Chicago

            6600 N. Mannheim Rd, Rosemont
              of 5, from 1,627 reviews
              3.0 out of 5.0

              Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. Rosemont Theatre and MB Financial Park at Rosemont are also within 3 mi (5 km).

              Congress Plaza Hotel C$108
              Congress Plaza Hotel

              Congress Plaza Hotel

              520 South Michigan Avenue, Chicago
                of 5, from 2,113 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.

                Hotel Felix Chicago C$108
                Hotel Felix Chicago

                Hotel Felix Chicago

                111 W Huron St, Chicago
                  of 5, from 3,578 reviews
                  4.0 out of 5.0

                  Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, whose 40 gondolas command unmatched skyline and lake views. Chicago-Red Metro Station is a 6-minute walk from the hotel.

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