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

Clearing Vacations

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

Hotwire can help you find your travel bliss with Clearing 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 Clearing

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 Clearing 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 Clearing well.

Clearing Flight + Hotel packages

Top Hotel Deals

See all 713 Hotels in Clearing
Chicago Marriott Midway

Chicago Marriott Midway

6520 South Cicero Avenue, Chicago
    3.5 out of 5.0
     
     

    Located in Clearing, this hotel is within 9 mi (15 km) of Toyota Park, University of Chicago, and Brookfield Zoo. Morton College and Douglas Park are also within ...

    Chicago Marriott Midway$161

    Chicago Marriott Midway$161
    Hilton Garden Inn Chicago/Midway Airport

    Hilton Garden Inn Chicago/Midway Airport

    6530 S Cicero Ave, Chicago
      3.0 out of 5.0
       
       

      Located in Clearing, this hotel is within 9 mi (15 km) of Toyota Park, University of Chicago, and Brookfield Zoo. Morton College and Douglas Park are also within ...

      Hilton Garden Inn Chicago/Midway Airport$153

      Hilton Garden Inn Chicago/Midway Airport$153
      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$149

        Congress Plaza Hotel$149
        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$95

          Warwick Allerton - Chicago$95
          River Hotel

          River Hotel

          75 East Wacker Drive, Chicago
            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 ...

            River Hotel$93

            River Hotel$93
            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$93

              Club Quarters Hotel, Central Loop$93
              Kimpton Hotel Allegro

              Kimpton Hotel Allegro

              171 W Randolph St, Chicago
                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 ...

                Kimpton Hotel Allegro$82

                Kimpton Hotel Allegro$82
                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$89

                  Hyatt Regency Chicago$89
                  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$87

                    Best Western Grant Park Hotel$87
                    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$89

                      Edward Hotel Chicago$89

                      Top Flight Deals

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