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Oswego Vacations

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

Hotwire can help you find your travel bliss with Oswego 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 Oswego

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 Oswego 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 Oswego well.

Oswego Flight + Hotel packages

Top Hotel Deals

See all 157 Hotels in Oswego
AmericInn by Wyndham Oswego

AmericInn by Wyndham Oswego

1050 Douglas Road, Oswego
    3.0 out of 5.0
     
     

    Situated in Oswego, this hotel is within 6 mi (10 km) of Grand Army of the Republic Hall, Aurora University, and Aurora Regional Fire Museum. Waubonsee Community ...

    AmericInn by Wyndham Oswego$110

    AmericInn by Wyndham Oswego$110
    Holiday Inn Express Hotel & Suites Chicago-Oswego

    Holiday Inn Express Hotel & Suites Chicago-Oswego

    2055 Wiesbrook Dr, Oswego
      2.5 out of 5.0
       
       

      Situated in Oswego, this hotel is within 6 mi (10 km) of Grand Army of the Republic Hall, Aurora University, and Aurora Regional Fire Museum. Waubonsee Community ...

      Holiday Inn Express Hotel & Suites Chicago-Oswego$116

      Holiday Inn Express Hotel & Suites Chicago-Oswego$116
      SureStay Plus Hotel by Best Western Chicago Lombard

      SureStay Plus Hotel by Best Western Chicago Lombard

      222 E 22nd Street, Lombard
        2.5 out of 5.0
         
         

        Situated in the suburbs, this hotel is 0.8 mi (1.3 km) from Yorktown Shopping Center and within 6 mi (10 km) of Lilacia Park and Drury Lane Theater. Belmont ...

        SureStay Plus Hotel by Best Western Chicago Lombard$60

        SureStay Plus Hotel by Best Western Chicago Lombard$60
        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 (0.5 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$61

          Red Roof Inn PLUS+ Chicago - Willowbrook$61
          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$84

            The Champagne Lodge & Luxury Suites$84
            Hotel Arista

            Hotel Arista

            2139 City Gate Ln, Naperville
              4.5 out of 5.0
               
               

              Situated in the business district, this luxury hotel is within 6 mi (10 km) of Centennial Beach, Chicago Premium Outlets, and Moser Tower and Millennium Carillon. ...

              Hotel Arista$143

              Hotel Arista$143
              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$70

                Chicago Club Inn & Suites$70
                Hyatt Place Chicago/Lombard/Oak Brook

                Hyatt Place Chicago/Lombard/Oak Brook

                2340 South Fountain Square Drive, Lombard
                  3.0 out of 5.0
                   
                   

                  Only 30 minutes by car from downtown Chicago and 5 minutes from highway I-88, Hyatt Place Chicago/Lombard runs a free shuttle to Oakbrook Center mall, 2.5 miles ...

                  Hyatt Place Chicago/Lombard/Oak Brook$84

                  Hyatt Place Chicago/Lombard/Oak Brook$84
                  Hyatt Regency Lisle near Naperville

                  Hyatt Regency Lisle near Naperville

                  1400 Corporetum Drive, Lisle
                    3.5 out of 5.0
                     
                     

                    Situated along I-88 (Reagan Memorial) high-tech business corridor, this sleek high-rise is within 25 miles of O'Hare, Midway, and historic downtown Naperville. ...

                    Hyatt Regency Lisle near Naperville$97

                    Hyatt Regency Lisle near Naperville$97
                    The Westin Lombard Yorktown Center

                    The Westin Lombard Yorktown Center

                    70 Yorktown Center, Lombard
                      4.5 out of 5.0
                       
                       

                      This smoke-free suburban Chicago hotel is 15 miles from downtown Chicago and next door to Yorktown Shopping Center. A complimentary area shuttle can be ...

                      The Westin Lombard Yorktown Center$118

                      The Westin Lombard Yorktown Center$118

                      Top Flight Deals

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