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Parkside Vacations

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

Hotwire can help you find your travel bliss with Parkside 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 Parkside

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 Parkside 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 Parkside well.

Parkside Flight + Hotel packages

Top Hotel Deals

See all 185 Properties in Parkside
Chicago South Loop Hotel

Chicago South Loop Hotel

11 W 26th Street, Chicago
    3.0 out of 5.0
     
     

    Located in Bronzeville, this hotel is within 1 mi (2 km) of State Street and McCormick Place. Guaranteed Rate Field and Soldier Field are also within 2 mi (3 ...

    Chicago South Loop Hotel$89

    Chicago South Loop Hotel$89
    The Champagne Lodge & Luxury Suites

    The Champagne Lodge & Luxury Suites

    16 W 621 S. Frontage Rd, Willowbrook
      3.5 out of 5.0
       
       

      This Willowbrook spa hotel is located about 20 miles southwest of downtown Chicago, 3 miles from the hiking and biking trails of Waterfall Glen. Cog Hill Golf ...

      The Champagne Lodge & Luxury Suites$112

      The Champagne Lodge & Luxury Suites$112
      Jaslin Hotel

      Jaslin Hotel

      261 West Cermak Rd, Chicago
        3.0 out of 5.0
         
         

        Located in Chinatown, this hotel is within 1 mi (2 km) of State Street and McCormick Place. Soldier Field and Field Museum of Natural History are also within ...

        Jaslin Hotel$89

        Jaslin Hotel$89
        Red Roof Inn PLUS+ Chicago - Willowbrook

        Red Roof Inn PLUS+ Chicago - Willowbrook

        7535 Kingery Highway, Willowbrook
          2.5 out of 5.0
           
           

          Situated in Willowbrook, this motel is 0.3 mi (0.6 km) from Willowbrook Community Park and within 3 mi (5 km) of Creekside Park and National Shrine of St. Therese. ...

          Red Roof Inn PLUS+ Chicago - Willowbrook$69

          Red Roof Inn PLUS+ Chicago - Willowbrook$69
          La Quinta Inn & Suites Chicago - Lake Shore

          La Quinta Inn & Suites Chicago - Lake Shore

          4900A S. Lake Shore Drive, Chicago
            3.0 out of 5.0
             
             

            Located in Kenwood, this hotel is within 1 mi (2 km) of Lakefront Trail and Chicago Museum of Science and Industry. University of Chicago is 1.8 mi (3 km) ...

            La Quinta Inn & Suites Chicago - Lake Shore$149

            La Quinta Inn & Suites Chicago - Lake Shore$149
            Chicago Club Inn & Suites

            Chicago Club Inn & Suites

            630 Pasquinelli Dr, Westmont
              3.0 out of 5.0
               
               

              Located in the Chicago suburbs of Westmont, this hotel is 1.5 miles from Hinsdale Golf Course, 6.25 miles from Chicago Botanic Garden, and 16.5 miles from the ...

              Chicago Club Inn & Suites$69

              Chicago Club Inn & Suites$69
              Hyatt Place Chicago Midway Airport

              Hyatt Place Chicago Midway Airport

              6550 S Cicero Ave, Chicago
                3.0 out of 5.0
                 
                 

                Situated near the airport, this hotel is within 9 mi (15 km) of Toyota Park, State Street, and Douglas Park. University of Chicago Medicine and Garfield Park ...

                Hyatt Place Chicago Midway Airport$121

                Hyatt Place Chicago Midway Airport$121
                La Quinta Inn & Suites Chicago Tinley Park

                La Quinta Inn & Suites Chicago Tinley Park

                7255 West 183rd St., Tinley Park
                  2.5 out of 5.0
                   
                   

                  Situated in the suburbs, this hotel is 0.5 mi (0.8 km) from Tinley Park Convention Center and 2.4 mi (3.8 km) from Hollywood Casino Amphitheatre. Gaelic Park ...

                  La Quinta Inn & Suites Chicago Tinley Park$76

                  La Quinta Inn & Suites Chicago Tinley Park$76
                  Red Roof Inn Chicago - Lansing

                  Red Roof Inn Chicago - Lansing

                  2450 East 173rd Street, Lansing
                    2.0 out of 5.0
                     
                     

                    Situated in Lansing, this hotel is within 1 mi (2 km) of Lansing Square Shopping Center, River Oaks Center, and Lan-Oak Park. South Holland Village Hall and ...

                    Red Roof Inn Chicago - Lansing$57

                    Red Roof Inn Chicago - Lansing$57
                    Super 8 by Wyndham Bridgeview/Chicago Area

                    Super 8 by Wyndham Bridgeview/Chicago Area

                    7887 W 79th St, Bridgeview
                      2.0 out of 5.0
                       
                       

                      Situated in Bridgeview, this hotel is 1.8 mi (2.9 km) from Toyota Park and within 9 mi (15 km) of Brookfield Zoo and Trinity Christian College. Marquette Park ...

                      Super 8 by Wyndham Bridgeview/Chicago Area$54

                      Super 8 by Wyndham Bridgeview/Chicago Area$54

                      Top Flight Deals

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