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Old Town Vacations

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

Hotwire can help you find your travel bliss with Old Town 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 Old Town

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 Old Town 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 Old Town well.

Old Town Flight + Hotel packages

Top Hotel Deals

See all 622 Hotels in Old Town
Hotel Lincoln

Hotel Lincoln

1816 N Clark Street, Chicago
    4.0 out of 5.0
     
     

    Located in Lincoln Park, this boutique hotel is within a 10-minute walk of Second City, Chicago History Museum, and Lincoln Park Zoo. North Avenue Beach and ...

    Hotel Lincoln$129

    Hotel Lincoln$129
    The Sono Chicago

    The Sono Chicago

    1428 N Cleveland Ave, Chicago
      3.5 out of 5.0
       
       

      Located in Near North Side, this bed & breakfast is within 2 mi (3 km) of Second City, John Hancock Center, and Lincoln Park Zoo. Chicago Water Tower and Merchandise ...

      At1426

      At1426

      1426 North North Park Avenue, Chicago
        3.5 out of 5.0
         
         
        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

                      Top Flight Deals

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