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Westchester Vacations

Pack those stellar shades. We have Westchester vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Westchester – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Westchester vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Westchester

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Westchester vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Westchester well.

Westchester Flight + Hotel packages

Top Hotel Deals

See all 765 Properties in Westchester
Hampton Inn Chicago/Westchester (Oak Brook)

Hampton Inn Chicago/Westchester (Oak Brook)

2222 Enterprise Drive, Westchester
    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 ...

    Hampton Inn Chicago/Westchester (Oak Brook)$76

    Hampton Inn Chicago/Westchester (Oak Brook)$76
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago
      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.

      Congress Plaza Hotel$104

      Congress Plaza Hotel$104
      Warwick Allerton - Chicago

      Warwick Allerton - Chicago

      701 North Michigan Avenue, Chicago
        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 ...

        Warwick Allerton - Chicago$94

        Warwick Allerton - Chicago$94
        River Hotel

        River Hotel

        75 East Wacker Drive, Chicago
          4.0 out of 5.0
           
           

          Located in The Loop, this hotel is within a 5-minute walk of Downtown Chicago and Chicago Theatre. Wrigley Building and Tribune Tower are also within 10 ...

          River Hotel$79

          River Hotel$79
          Club Quarters Hotel, Central Loop

          Club Quarters Hotel, Central Loop

          111 West Adams Street, Chicago
            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 ...

            Club Quarters Hotel, Central Loop$64

            Club Quarters Hotel, Central Loop$64
            Hyatt Regency Chicago

            Hyatt Regency Chicago

            151 East Wacker Dr, Chicago
              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 ...

              Hyatt Regency Chicago$119

              Hyatt Regency Chicago$119
              Best Western Grant Park Hotel

              Best Western Grant Park Hotel

              1100 S Michigan Ave, Chicago
                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 ...

                Best Western Grant Park Hotel$95

                Best Western Grant Park Hotel$95
                Edward Hotel Chicago

                Edward Hotel Chicago

                6600 N. Mannheim Rd, Rosemont
                  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. ...

                  Edward Hotel Chicago$71

                  Edward Hotel Chicago$71
                  Chicago's Essex Inn

                  Chicago's Essex Inn

                  800 S Michigan Ave, Chicago
                    3.5 out of 5.0
                     
                     

                    Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, ...

                    Chicago's Essex Inn$134

                    Chicago's Essex Inn$134
                    Palmer House a Hilton Hotel

                    Palmer House a Hilton Hotel

                    17 E Monroe St, Chicago
                      4.0 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 ...

                      Palmer House a Hilton Hotel$105

                      Palmer House a Hilton Hotel$105

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