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Find a lower price online up to 24-hours prior to check-in and we’ll refund the difference.

Save up to $387^ on holiday packages when you bundle a hotel and flight.

With more than 550 airlines and 665,000 properties worldwide, it’s easy to find your best holiday.

Top Chicago Holiday Packages

Top Chicago Holiday Packages - 4 Nights

Top Chicago Holiday Packages - 6 Nights

Chicago Holiday Packages

Chicago, Illinois, is the perfect choice for an American holiday—it has a busy, powerful vibe similar to New York, with just as much to do and see. Chicago packages are your ticket to an American Midwest secret: “The Windy City” has some of the best food, shopping and nightlife in the U.S.—at least, according to the locals! Why not decide for yourself on your next holiday?

Things to Do in Chicago

Navy Pier is a can’t-miss activity for any holiday in Chicago. The 45m-tall Ferris wheel is sure to catch your attention; take a spin for great city views. Then do your best sailor swagger into the shops, where you just might find those perfect skyline-shaped chocolates. Don’t be “a-freud” to stop and chat with the statue of TV-psychologist Bob Newhart, whose couch is designed for therapeutic confessions (and photo ops). Hungry? Travel to the tropics inside Crystal Gardens, a one-acre greenhouse with palm trees, fountains and a variety of restaurants.

If you’re in the mood for some education, or the weather just isn’t on your side, explore indoors at one of Chicago’s museums. Always wanted to see the world from an ant’s perspective or learn about man-eating lions in Kenya? The Field Museum of Natural history, one of the largest in the world, is your playground. You could also book a Chicago car hire and head north to the Illinois Railway Museum or south to the Museum of Science and Industry.

Shopping, Dining & Nightlife

The money you’ve saved with our Chicago package deals is probably burning a hole in your pocket, so it’s time to decide: What’s your shopping style? The Magnificent Mile lives up to its name, with world-famous luxury brands and posh boutiques. In the Loop neighbourhood, rock collectors can find the perfect marquise cut on Jewelers Row, while bargain hunters can dig through discount racks on State Street. A Chicago holiday near Millennium Park is the perfect home base for shopaholic getaways, with both these neighbourhoods within walking distance.

You can show off your new diamonds at dinner without even leaving Mag Mile—it’s one of the best neighbourhoods for upscale dining. However, Chicago holidays are best spent exploring; go northwest to find up-and-coming Lincoln Park, filled to the brim with the vanguard of experimental cuisine. Get your hands on mozzarella balloons, inside-out eggs benedict and crispy pig’s ears, and your taste buds will never be the same.

Swanky sightseers can keep their holiday going into the wee hours in Gold Coast, an area that is, you guessed it, on the Lake Michigan coast and very exclusive. Head over to stylish Rush Street to get your groove on with live jazz, reggae or funk. For the younger (or just hipper) crowd, Wicker Park is all about trendy cocktails, groovy tunes and a laid-back vibe. Plus, it’s got a subway stop on the 24-hour Blue Line, so you can easily get back downtown without even springing for a cab.

What’s Next?

The next steps are easy—listen to your holiday self and book your getaway with Wotif. We have the best Chicago hotel packages, because you can mix and match with flights to the same destination to create your perfect escape. Check us out today.

Need insider tips on must-see attractions in Chicago? Check out our Chicago travel guide!


Guide to Exploring Chicago

Family Hotels in Chicago

Embassy Suites Chicago Downtown Magnificent Mile

Embassy Suites Chicago Downtown Magnificent Mile

511 North Columbus Drive, Chicago, IL
    4.0 out of 5.0
     
     
    4.7 out of 5 (3 reviews)

    Located in Near North Side, this hotel is within a 5-minute walk of Chicago Riverwalk, Tribune Tower, and Michigan Avenue. Northwestern Memorial Hospital and ...

    from AU$288

    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St, Chicago, IL
      4.0 out of 5.0
       
       
      2.3 out of 5 (3 reviews)

      Located in The Loop, this spa hotel is within a 5-minute walk of Art Institute of Chicago and Millennium Park. Chicago Theatre and Willis Tower are also within ...

      from AU$241

      Embassy Suites Chicago Downtown

      Embassy Suites Chicago Downtown

      600 N State St, Chicago, IL
        4.0 out of 5.0
         
         
        5.0 out of 5 (1 reviews)

        Located in River North, this hotel is steps from Chinese Consulate and State Street. Tribune Tower and Wrigley Building are also within 10 minutes. Grand Station ...

        from AU$262

        Hyatt Regency Chicago

        Hyatt Regency Chicago

        151 East Wacker Dr, Chicago, IL
          4.0 out of 5.0
           
           
          3.0 out of 5 (2 reviews)

          Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Grant Park and Chicago Theatre are also within 10 minutes. ...

          from AU$249

          Romantic Hotels in Chicago

          The Champagne Lodge & Luxury Suites

          The Champagne Lodge & Luxury Suites

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

            Situated in Willowbrook, this romantic hotel is 1.9 mi (3.1 km) from Willowbrook Community Park and 2.7 mi (4.3 km) from National Shrine of St. Therese. Burr ...

            from AU$185

            LondonHouse Chicago, Curio Collection by Hilton

            LondonHouse Chicago, Curio Collection by Hilton

            85 East Wacker Drive, Chicago, IL
              4.5 out of 5.0
               
               
              2.0 out of 5 (1 reviews)

              Located in The Loop, this luxury hotel is steps from Chicago Riverwalk and Michigan Avenue. Tribune Tower and Grant Park are also within 10 minutes. Clark-Lake ...

              from AU$188

              Palmer House a Hilton Hotel

              Palmer House a Hilton Hotel

              17 E Monroe St, Chicago, IL
                4.0 out of 5.0
                 
                 
                2.3 out of 5 (3 reviews)

                Located in The Loop, this spa hotel is within a 5-minute walk of Art Institute of Chicago and Millennium Park. Chicago Theatre and Willis Tower are also within ...

                from AU$241

                Trump International Hotel & Tower Chicago

                Trump International Hotel & Tower Chicago

                401 N Wabash Ave, Chicago, IL
                  5.0 out of 5.0
                   
                   
                  5.0 out of 5 (1 reviews)

                  Located in River North, this family-friendly Chicago hotel is within a 5-minute walk of Wrigley Building, Chicago Riverwalk, and State Street. Tribune Tower ...

                  from AU$479

                  ^Savings based on all package bookings made with Flight + Hotel on Wotif.com from January 1, 2018 to December 31, 2018, as compared to the 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.

                  *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.