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

Save up to C$603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


Westchester Vacation Packages

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

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

See all 766 hotels in Westchester
Hampton Inn Chicago/Westchester (Oak Brook) C$97
Hampton Inn Chicago/Westchester (Oak Brook)

Hampton Inn Chicago/Westchester (Oak Brook)

2222 Enterprise Drive, Westchester
     
    4.3
    of 5, from 694 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, Oakbrook Center Mall, and Drury Lane Theater. Brookfield Zoo and Stevenson Park are also within 6 mi (10 km).

    Congress Plaza Hotel C$137
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago
       
      3.6
      of 5, from 2,350 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.

      Warwick Allerton - Chicago C$117
      Warwick Allerton - Chicago

      Warwick Allerton - Chicago

      701 North Michigan Avenue, Chicago
         
        4.1
        of 5, from 8,846 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.

        River Hotel C$125
        River Hotel

        River Hotel

        75 East Wacker Drive, Chicago
           
          4.2
          of 5, from 4,260 reviews
          4.0 out of 5.0

          Located in The Loop, this hotel is steps from Downtown Chicago and Chicago Riverwalk.

          Club Quarters Hotel, Central Loop C$122
          Club Quarters Hotel, Central Loop

          Club Quarters Hotel, Central Loop

          111 West Adams Street, Chicago
             
            4.3
            of 5, from 6,089 reviews
            4.0 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.

            Kimpton Hotel Allegro C$113
            Kimpton Hotel Allegro

            Kimpton Hotel Allegro

            171 W Randolph St, Chicago
               
              4.3
              of 5, from 3,950 reviews
              4.0 out of 5.0

              Located 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 C$155
              Hyatt Regency Chicago

              Hyatt Regency Chicago

              151 East Wacker Dr, Chicago
                 
                4.4
                of 5, from 9,380 reviews
                4.0 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.

                Best Western Grant Park Hotel C$105
                Best Western Grant Park Hotel

                Best Western Grant Park Hotel

                1100 S Michigan Ave, Chicago
                   
                  4.3
                  of 5, from 916 reviews
                  2.5 out of 5.0

                  Favored 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

                  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.