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West Town Vacations

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

Hotwire can help you find your travel bliss with West 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 West 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 West 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 West Town well.

West Town Flight + Hotel packages

Top Hotel Deals

See all 671 Hotels in West Town
The Robey

The Robey

2018 W. North Ave., Chicago
    3.5 out of 5.0
     
     

    Located in West Town, this hotel is within 3 mi (5 km) of Humboldt Park, United Center, and Merchandise Mart. Lincoln Park Zoo is 3 mi (4.9 km) away.

    Ginosi 747 Apartel

    Ginosi 747 Apartel

    747 N May St., Chicago
      2.5 out of 5.0
       
       

      This apartment building is located in Chicago (West Town), close to Union Park, Willis Tower, and Skydeck Ledge. Also nearby are John Hancock Center and University ...

      Urban Holiday Lofts

      Urban Holiday Lofts

      2014 W Wabansia, Chicago
        1.5 out of 5.0
         
         

        Located in West Town, this hostel is within 3 mi (5 km) of Humboldt Park, United Center, and Lincoln Park Zoo. Merchandise Mart is 3 mi (4.8 km) away.

        Ruby Room

        Ruby Room

        1743-45 W Division St, Chicago
          2.5 out of 5.0
           
           

          Located in West Town, this spa hotel is within 3 mi (5 km) of Humboldt Park, John Hancock Center, and Willis Tower. Skydeck Ledge and University of Illinois ...

          Ruby Room$160

          Ruby Room$160
          Holiday Jones

          Holiday Jones

          1659 W Division Street, Chicago
            1.5 out of 5.0
             
             

            Located in West Town, this hostel is within 3 mi (5 km) of Humboldt Park, John Hancock Center, and Willis Tower. Skydeck Ledge and University of Illinois Chicago ...

            Wicker Park Inn

            Wicker Park Inn

            1331 N Wicker Park Ave, Chicago
              2.5 out of 5.0
               
               

              Located in West Town, this bed & breakfast is within 3 mi (5 km) of Humboldt Park, John Hancock Center, and United Center. Merchandise Mart and Chicago Water ...

              Grand Local Ave Luxury Apartments

              Grand Local Ave Luxury Apartments

              1411 W Grand Ave, Chicago
                3.5 out of 5.0
                 
                 

                Located in West Town, this apartment building is within 3 mi (5 km) of United Center, University of Illinois Chicago, and Willis Tower. Skydeck Ledge and John ...

                West Town Guest House

                West Town Guest House

                1413 N Ashland Ave, Chicago
                  3.0 out of 5.0
                   
                   

                  Located in West Town, this apartment building is within 3 mi (5 km) of Second City, John Hancock Center, and Willis Tower. Skydeck Ledge and University of Illinois ...

                  Hip 3BR in Wicker Park by Sonder

                  Hip 3BR in Wicker Park by Sonder

                  West Division Street and Leavitt Street, Chicago
                    3.5 out of 5.0
                     
                     

                    Located in West Town, this apartment building is 1.1 mi (1.8 km) from Humboldt Park and within 3 mi (5 km) of United Center and Merchandise Mart. Garfield Park ...

                    Sophisticated 1BR in Wicker Park by Sonder

                    Sophisticated 1BR in Wicker Park by Sonder

                    North Damen Avenue and Evergreen, Chicago
                      3.5 out of 5.0
                       
                       

                      Located in West Town, this apartment building is within 3 mi (5 km) of Humboldt Park, United Center, and Merchandise Mart. Second City and Chicago History Museum ...

                      Top Flight Deals

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