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Countryside Vacations

Pack those stellar shades. We have Countryside 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 Countryside – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Countryside 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 Countryside

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 Countryside 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 Countryside well.

Countryside Flight + Hotel packages

Top Hotel Deals

See all 714 Properties in Countryside
Best Western Plus Chicagoland - Countryside

Best Western Plus Chicagoland - Countryside

6251 Joliet Rd, Countryside
    3.5 out of 5.0
     
     

    Best Western Plus Chicagoland - Countryside is a 15-minute drive from Midway Airport, and 20 minutes from O'Hare International. Guests can drive to Brookfield ...

    Best Western Plus Chicagoland - Countryside$105

    Best Western Plus Chicagoland - Countryside$105
    Holiday Inn Chicago - Countryside / Lagrange

    Holiday Inn Chicago - Countryside / Lagrange

    6201 Joliet Rd, Countryside
      3.0 out of 5.0
       
       

      Situated in Countryside, this hotel is within 6 mi (10 km) of Creekside Park, Brookfield Zoo, and Willowbrook Community Park. Toyota Park and Veterans Memorial ...

      Holiday Inn Chicago - Countryside / Lagrange$103

      Holiday Inn Chicago - Countryside / Lagrange$103
      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$76

              Club Quarters Hotel, Central Loop$76
              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

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.