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Westchester Vacation Packages

Making your way to Westchester?

Save Time and Money with a Westchester Package Deal

Expedia can help you save money with a flight and hotel package deal. There is nothing better than pairing your accommodation and flight deals for additional savings. With the extra cash, now you can shop a little more in Westchester.

15% in potential savings is waiting for those savvy vacationers who book deals.

Our impressive international database allows you to browse 321,000 hotels worldwide and up to 400 partner airlines, and it also rewards you with great savings.

There's no better time than right now to finalize your trip, with some of the best prices and deals at Expedia.

You never have to worry about changing your vacation plans, as we do not charge additional cancellation fees for almost all of our bookings.

Westchester Vacation Packages

It's in Chicago, an excellent destination that is home to 2,700,000 people. Hitting the tarmac at O'Hare International Airport? Grab your luggage, head 9 miles to the south and you'll be in Westchester. When you're ready to go exploring, you'll be 14 miles from the heart of the city.

There's so much to discover in the local area! Be sure to stop at the Brookfield Zoo and Frank Lloyd Wright Home and Studio. You may also like Unity Temple and Yorktown Shopping Centre. Other nearby communities, like Hillside and La Grange Park, are well worth your time.

Vacationers from all corners of the world make sure they visit the University of Chicago. This renowned sight is 6 miles from the heart of the city.

Navy Pier and the Lincoln Park Zoo are just two of the entertaining diversions that are waiting for you in this city. The Chicago Cultural Centre and the Merchandise Mart are also worth a visit.

Hit the greens at the local courses, such as the Oak Brook Golf Course and the Fresh Meadow Golf Club. Fine tune your putting and then go to the nineteenth hole for a few cold ones.

You never know what you may find at the Graue Mill and Museum, Mayslake Peabody Mansion and Forest Home Cemetery. These historic sites have their fair share of tales to tell.

Accommodation in Westchester

A great place to stay goes a long way towards optimal relaxation. You can check out some of the best hotels in Westchester on Expedia's travel guide.

Start your quest for a dreamy Westchester hotel by checking out the services and amenities at The Hyatt Lodge at McDonald's Campus, located at 2815 Jorie Blvd, and the Le Méridien Chicago - Oakbrook Centre, at 2100 Spring Road. If you want to see what the cheaper options are like, the Extended Stay America - Chicago - Elmhurst - O'Hare, at 550 W Grand Ave, and the Extended Stay America - Chicago - Westmont - Oak Brook, at 855 Pasquinelli Dr, are worthy options too.


Top Hotel Deals

See all 767 hotels in Westchester
Hampton Inn Chicago/Westchester (Oak Brook)
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 miles (5 km) of Oak Brook Golf Course, Oakbrook Center Mall and Drury Lane Theater. Brookfield Zoo and Stevenson Park are also within 6 miles (10 km).

    Congress Plaza Hotel £76
    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

      Located in The Loop, this hotel is steps away from Columbia College Chicago, Museum of Contemporary Photography and Auditorium Building and Theatre. Fine Arts Building and Buckingham Fountain are also within 10 minutes.

      Warwick Allerton - Chicago
      Warwick Allerton - Chicago

      Warwick Allerton - Chicago

      701 North Michigan Avenue, Chicago
         
        4.1
        of 5, from 8,847 reviews
        4.0 out of 5.0

        Located in Near North Side, this hotel is within a 5-minute walk of Downtown Chicago and Chicago Water Tower. John Hancock Center and Tribune Tower are also within 10 minutes.

        River Hotel
        River Hotel

        River Hotel

        75 East Wacker Drive, Chicago
           
          4.2
          of 5, from 4,259 reviews
          4.0 out of 5.0

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

          Club Quarters Hotel, Central Loop £67
          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

            Located in The Loop, this hotel is within a 10-minute walk of Downtown Chicago, Willis Tower and Skydeck Ledge. Art Institute of Chicago and Ford Center for the Performing Arts Oriental Theatre are also within 10 minutes.

            Kimpton Hotel Allegro £66
            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, this romantic hotel is within a 5-minute walk of Downtown Chicago and Ford Center for the Performing Arts Oriental Theatre. Merchandise Mart and Chicago Theatre are also within 10 minutes.

              Hyatt Regency Chicago
              Hyatt Regency Chicago

              Hyatt Regency Chicago

              151 East Wacker Dr, Chicago
                 
                4.4
                of 5, from 9,381 reviews
                4.0 out of 5.0

                Located in The Loop, this eco-friendly hotel is steps away from Downtown Chicago, Chicago Riverwalk and Michigan Avenue Bridge. Chicago Theatre and Millennium Park are also within 15 minutes.

                Best Western Grant Park Hotel £58
                Best Western Grant Park Hotel

                Best Western Grant Park Hotel

                1100 S Michigan Ave, Chicago
                   
                  4.3
                  of 5, from 918 reviews
                  2.5 out of 5.0

                  Located in The Loop, this hotel is within a 10-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Field Museum of Natural History are also within 1 mi (2 km).

                  Top Flight + Hotel Deals

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