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Chicago Vacation

Does Expedia have vacation package deals to Chicago?

Yes! Expedia has some fantastic Chicago travel packages Combining your bookings is one of the simplest ways to save cash and time — and get your adventure off on the right foot.

How much can I save with a Chicago vacation package?

Smart jetsetters can save up to C$590* by booking a package deal on Expedia.

Can I choose my airline with a Chicago Expedia vacation package?

Our enormous global database lists more than 750,000 properties worldwide and 400 partner airlines. With such a broad range of options, crafting your dream vacation will be easy!

Do I lose money if I change my mind after I have booked my Chicago vacation package?

Still undecided? There are no hidden fees from us if you change your mind for almost any reservation.

What are the best 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.

A vacation is a great time to slow down and unwind. It's also the ideal time to embark on some new experiences!

Kick-start your trip to Chicago by checking out some of these activities:

Jump onto our Chicago things to do page for a full list.

What types of accommodations are available in Chicago?

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.

Is there an airport in 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.ca from January through December 2019, 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.


Guide to Exploring around Chicago


Top Flight + Hotel Deals in Chicago

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Best Lodging Options Near Chicago

See all 2,055 properties in Chicago
Hyatt Regency Chicago CA $157
Reviewed on Dec. 12, 2019
See details
 
Hyatt Regency Chicago

Hyatt Regency Chicago

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

    Very accessible to the places I needed to be for my conference at the Sheraton across the river and way better prices

    Swissotel - Chicago CA $136
    Reviewed on Dec. 15, 2019
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    Swissotel - Chicago

    Swissotel - Chicago

    323 E Wacker Dr, Chicago, IL
       
      4.4 of 5
      4.5 out of 5.0 Stars

      Attention to the needs of the guest and detail to the small stuff that matters. We enjoyed every moment of our experience at this unique property.

      Warwick Allerton - Chicago CA $104
      Reviewed on Dec. 14, 2019
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      Warwick Allerton - Chicago

      Warwick Allerton - Chicago

      701 North Michigan Avenue, Chicago, IL
         
        4.1 of 5
        4.0 out of 5.0 Stars

        Convenient location, excellent services, and perfect accommodation!

        Radisson Blu Aqua Hotel Chicago CA $167
        Reviewed on Dec. 11, 2019
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        Radisson Blu Aqua Hotel Chicago

        Radisson Blu Aqua Hotel Chicago

        221 N Columbus Dr, Chicago, IL
           
          4.5 of 5
          4.5 out of 5.0 Stars

          Property was well maintained. Restaurant staff was lacking. Very poor service.

          Hilton Chicago- Michigan Ave Cultural Mile CA $125
          Reviewed on Dec. 11, 2019
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          Hilton Chicago- Michigan Ave Cultural Mile

          Hilton Chicago- Michigan Ave Cultural Mile

          720 S Michigan Ave, Chicago, IL
             
            4.2 of 5
            4.0 out of 5.0 Stars

            Ruphos the bell hop was awesome and he is a very aprochable and went above and beyond to make our trip great.

            La Quinta Inn & Suites by Wyndham Chicago Downtown CA $103
            Reviewed on Dec. 10, 2019
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            La Quinta Inn & Suites by Wyndham Chicago Downtown

            La Quinta Inn & Suites by Wyndham Chicago Downtown

            1 S Franklin Street, Chicago, IL
               
              4.5 of 5
              3.0 out of 5.0 Stars

              The facility was very nice and clean. Staff was helpful.

              Hilton Chicago O'Hare Airport CA $145
              Reviewed on Dec. 2, 2019
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              Hilton Chicago O'Hare Airport

              Hilton Chicago O'Hare Airport

              Ohare International Airport, Chicago, IL
                 
                3.9 of 5
                4.0 out of 5.0 Stars

                We use this hotel to stay the night before our early AM flight. Excellent! We only needed to walk and we are at the gate literally.

                Eurostars Magnificent Mile, previously Dana Hotel CA $124
                Reviewed on Dec. 13, 2019
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                Eurostars Magnificent Mile, previously Dana Hotel

                Eurostars Magnificent Mile, previously Dana Hotel

                660 North State Street, Chicago, IL
                   
                  4.4 of 5
                  4.0 out of 5.0 Stars

                  The whole set up was unique, really enjoyed my stay.

                  Top things to do in Chicago

                  See all 296 things to do in Chicago