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Oak Lawn Vacations

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

Hotwire can help you find your travel bliss with Oak Lawn 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 Oak Lawn

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 Oak Lawn 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 Oak Lawn well.

Oak Lawn Flight + Hotel packages

Top Hotel Deals

See all 697 Hotels in Oak Lawn
Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

9333 S Cicero Ave, Oak Lawn
    3.5 out of 5.0
     
     

    Situated in Oak Lawn, this hotel is within 6 mi (10 km) of Marquette Park, Toyota Park, and Trinity Christian College. Auburn Park and Morton College are also ...

    Hilton Chicago/Oak Lawn$112

    Hilton Chicago/Oak Lawn$112
    Midway Inn & Suites

    Midway Inn & Suites

    9320 South Cicero Ave, Oak Lawn
      2.0 out of 5.0
       
       

      Situated in Oak Lawn, this motel is within 6 mi (10 km) of Marquette Park, Toyota Park, and Trinity Christian College. Auburn Park and Morton College are also ...

      Miami Inn & Suites

      Miami Inn & Suites

      9041 S Cicero Ave, Oak Lawn
        2.0 out of 5.0
         
         

        Situated in Oak Lawn, this motel is within 6 mi (10 km) of Marquette Park, Toyota Park, and Trinity Christian College. Morton College and Gaelic Park are also ...

        Gateway Inn

        Gateway Inn

        4657 W 95th Street, Oak Lawn
          2.5 out of 5.0
           
           

          Situated in Oak Lawn, this motel is 0.5 mi (0.8 km) from Childrens Museum of Oak Lawn and 2.4 mi (3.8 km) from Chicago Ridge Shopping Mall. Marquette Park is ...

          Central Loop Hotel

          Central Loop Hotel

          111 West Adams Street, Chicago
            4.0 out of 5.0
             
             

            Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago ...

            Central Loop Hotel$133

            Central Loop Hotel$133
            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$117

              River Hotel$117
              The Whitehall Hotel

              The Whitehall Hotel

              105 E Delaware Pl, Chicago
                4.0 out of 5.0
                 
                 

                Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

                The Whitehall Hotel$101

                The Whitehall Hotel$101
                Wyndham Grand Chicago Riverfront

                Wyndham Grand Chicago Riverfront

                71 E Wacker Dr, Chicago
                  4.0 out of 5.0
                   
                   

                  This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district ...

                  Wyndham Grand Chicago Riverfront$134

                  Wyndham Grand Chicago Riverfront$134
                  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$97

                    Congress Plaza Hotel$97
                    Hotel Felix Chicago

                    Hotel Felix Chicago

                    111 W Huron St, Chicago
                      4.0 out of 5.0
                       
                       

                      Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, ...

                      Hotel Felix Chicago$87

                      Hotel Felix Chicago$87

                      Top Flight Deals

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