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Chicago Vacation Packages

Save Time and Money with Chicago Vacation Packages

Have you thought about securing a Chicago vacation package? It's a piece of cake with Expedia, and you'll be able to buy some nice dinners or presents for your friends back home with the cash you save.

Up to 40,450 YEN* can be saved when you secure your package deal on Expedia.

Explore our international database of more than 400 airline partners and 750,000 worldwide properties. Too many on there to select from? Don't worry — we can help you decide!

You can postpone your vacation bookings with us because we do not charge cancellation fees for almost all of our bookings.

Places to Visit in Chicago

Preparing for your trip to Chicago? Need some info about what to see when you arrive? That's where we can assist!

Take it from us, your bucket list will be heaps shorter after a trip to Chicago! Famed attractions like the Art Institute of Chicago and Willis Tower should be some of your first ports of call. The McCormick Place and the University of Illinois Chicago also draw in crowds of travelers from all across the globe.

You're going to find yourself surrounded by terrific things to do and see, including Navy Pier and the Lincoln Park Zoo. If you're dying to get the most out of your stay, also check out Lincoln Park and the Chicago Cultural Center.

Millennium Park is an oasis amid the bustle of everyday life. Pull off your shoes and feel the cool grass beneath your feet or simply lie on your back and spot shapes in the clouds. Adventurers in this destination have heaps of options. Those who are a little queasy around heights might want to look away, but anyone who's curious about skyscrapers can't miss John Hancock Center. Towering high above the ground, it's a beloved fixture of the area's skyline. Still have some time on your hands? Want to catch a sunrise among some spectacular scenery? Skydeck Ledge boasts glorious views that deserve to be photographed.

Popular Activities for your Chicago Vacation

Vacations are pretty great already. But throwing yourself into the fantastic activities on offer always makes them better!

Your trip to Chicago is about to get a whole lot more exciting. There are plenty of activities available, including:

For a more complete list of activities, jump onto our Chicago things to do page.

Chicago Accommodations

You can expect a large range of accommodations when you head to Chicago. With 165 properties on offer, it won't be an issue booking a cozy place to sleep for your next luxury getaway or cheap vacation.

The Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street) are two of the higher-end options in Chicago. Book a room at either and you're bound to have some of the nicest rooms in town. Looking for somewhere cheaper? The Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are a couple of places that won't break the bank.

Of course, another great option is to stay just a stone's throw from the Art Institute of Chicago. You can do this by making a reservation at The Langham, Chicago, which is just 0.6 miles (1 km) away. Also in demand is the JW Marriott Chicago, a mere 0.5 miles (0.8 km) away.

Nearest Airports to Chicago

The airport probably isn't going to be the most exhilarating moment of your vacation, but there's nothing like the feeling of knowing that your well-earned trip to Chicago is a mere plane ride away! Once you hit the ground at Midway International Airport (MDW), you'll be 9 miles (14 km) from the center of town.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Guide to Exploring Chicago


Top Hotel Deals

See all 1,649 Properties in Chicago
Hotel Essex Chicago ¥9,653
Reviewed on Jun 21, 2019
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Hotel Essex Chicago

Hotel Essex Chicago

800 S Michigan Ave, Chicago, IL
     
    4.4 of 5
    4.0 out of 5.0 Stars

    Clean contemporary rooms. Operable windows. Beautiful location on park. Friendly staff. A good value. And reasonable overnight parking nearby.

    Congress Plaza Hotel ¥9,358
    Reviewed on Jun 22, 2019
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    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL
       
      3.7 of 5
      3.5 out of 5.0 Stars

      The staff was great! The location on Michigan Ave was perfect.

      Hyatt Regency Chicago ¥11,590
      Reviewed on Jun 23, 2019
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      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago, IL
         
        4.4 of 5
        4.0 out of 5.0 Stars

        Close to river and convenient to trains and points of interest.

        Hyatt Regency McCormick Place ¥11,590
        Reviewed on Jun 23, 2019
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        Hyatt Regency McCormick Place

        Hyatt Regency McCormick Place

        2233 S Martin Luther King Dr, Chicago, IL
           
          4.4 of 5
          4.0 out of 5.0 Stars

          The staff were helpful and friendly. It was easy to check in. The room was clean

          Central Loop Hotel ¥8,113
          Reviewed on Jun 21, 2019
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          Central Loop Hotel

          Central Loop Hotel

          111 West Adams Street, Chicago, IL
             
            4.2 of 5
            4.0 out of 5.0 Stars

            Location was convenient to Union Station, CIBC theater, Art Institute.

            Wyndham Grand Chicago Riverfront ¥10,855
            Reviewed on Jun 23, 2019
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            Wyndham Grand Chicago Riverfront

            Wyndham Grand Chicago Riverfront

            71 E Wacker Dr, Chicago, IL
               
              4.4 of 5
              4.0 out of 5.0 Stars

              I enjoyed my stay here! The location was ideal - directly across from a hop on/hop off bus in the heart of downtown. It made touring the area easy. The staff was friendly and rooms clean and comfortable.

              River Hotel ¥8,596
              Reviewed on Jun 23, 2019
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              River Hotel

              River Hotel

              75 East Wacker Drive, Chicago, IL
                 
                4.2 of 5
                4.0 out of 5.0 Stars

                Exceeded my expectations Would recommend both the River and Expedia

                Travelodge by Wyndham Downtown Chicago ¥10,144
                Reviewed on Jun 23, 2019
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                Travelodge by Wyndham Downtown Chicago

                Travelodge by Wyndham Downtown Chicago

                65 E Harrison St, Chicago, IL
                   
                  3.3 of 5
                  2.0 out of 5.0 Stars

                  Good location, connected to excellent restaurant. Interior was dingy and room had a musty odor. For the price and location, will definitely stay here again.

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