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Oak Park Vacations

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

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

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 Park 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 Park well.

Top Hotel Deals

See all 749 Hotels in Oak Park
Carleton of Oak Park

Carleton of Oak Park

1110 Pleasant St, Oak Park
    3.0 out of 5.0
     
     

    Just 10 miles and 15 minutes by train from downtown Chicago, this hotel is 1 block from the train stop; it is also 8 blocks from the Hemingway Museum.

    Carleton of Oak Park$134

    Carleton of Oak Park$134
    Write Inn Hotel

    Write Inn Hotel

    211 N Oak Park Ave, Oak Park
      2.5 out of 5.0
       
       

      Located in the heart of Oak Park, this hotel is within 6 mi (10 km) of Garfield Park Conservatory, Brookfield Zoo, and Garfield Park. United Center and Humboldt ...

      Write Inn Hotel$139

      Write Inn Hotel$139
      Bishops Hall

      Bishops Hall

      605 Iowa Street, Oak Park
        3.5 out of 5.0
         
         

        Situated in Oak Park, this bed & breakfast is within 6 mi (10 km) of Garfield Park Conservatory, Brookfield Zoo, and Garfield Park. United Center and Humboldt ...

        Harvey House Bed & Breakfast

        Harvey House Bed & Breakfast

        107 South Scoville Avenue, Oak Park
          4.0 out of 5.0
           
           

          Situated in Oak Park, this romantic bed & breakfast is within 6 mi (10 km) of Garfield Park Conservatory, Brookfield Zoo, and Garfield Park. University of Illinois ...

          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$99

              Warwick Allerton - Chicago$99
              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$108

                River Hotel$108
                Club Quarters Hotel, Central Loop

                Club Quarters Hotel, Central Loop

                111 West Adams Street, Chicago
                   
                   

                  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$108

                  Club Quarters Hotel, Central Loop$108
                  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

                      Top Flight Deals

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