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Top Holiday Package Deals in Chicago

Holiday In Chicago

When you’re trying to blow out of town, catch the next big gust to the “Windy City”. Known for its bustling riverfront venues, a lively arts scene and Midwestern gumption, no one can accuse “Chi-town” of actually being shy. If you want to kick it on the banks of enormous Lake Michigan, you’ll be welcomed with open arms. But before embarking on holidays to Chicago, Illinois, you should know that natives are serious about a few things: Deep-dish pizza, professional sports and making you laugh your arse off. As it happens, we’re serious about those, too.

Things to Do in Chicago

Chicago holidays are all about history and shouting baseball fans. Hit two balls with one bat at Wrigley Field, built in 1914. Once you’ve caught a pop fly and eaten your share of ball park wieners, chill out in Millennium Park in the famous Chicago Loop. From that prime location, you’ll be within walking distance to popular activities, like the Art Institute of Chicago, Chicago Cultural Center and the Cloud Gate sculpture. Sure, that last bit is a bean-shaped art installation, but add planking and people-watching and you’ll have pure social media gold. Now, if there’s one thing you’ve got to do on your Chicago holiday, it’s amble around the Chicago Riverwalk. Tuck into the many cafes and shops or head to Navy Pier for carnival rides—no boot camp required. Public transit is stellar around the city centre, but check out our fantastic Chicago car hire options to ease your commute to Lincoln Park Zoo or the ballpark.

Shopping, Dining & Nightlife

They don’t call North Michigan Avenue the “Magnificent Mile” for nothin’. This street is lined with some of the best shopping haunts near the Great Lakes. Don’t know where those are? Look eastward. You can easily watch the dollars turn into designer clothes, so it’s a good thing you’re about to save on our great Chicago packages. Just saying. For one-of-a kind finds, follow the current trends to River North, Chi-town’s largest arts district.

Ask any Chicagoan where to find the best deep-dish pizza—you’ll get a different story from everyone. That just means you need to try them all! Between saucy slices, remember that Chicago is an international city, and you can stay in neighbourhoods based on the eats you plan to devour. Graze on chicken Vesuvio in Little Italy or find ma po tofu by the bowl in Chinatown. This flavourful favourite is served all over the city, just in case the craving strikes.

In Chicago, you’re ether feeling the blues or laughing till you cry. Considered “The World Capital of the Blues”, this lakeside destination can croon along with the greats like Muddy Waters and Koko Taylor. Speaking of greats, comedians Bill Murray, Tina Fey and many others got their starts at The Second City Theatre, a comedy club that’s been LOL-ing in Old Town since 1959.

What’s Next?

If we lost you at “deep-dish pizza”, we’ll keep it simple. Book Chicago holiday packages with lastminute.com.au for the best deals on your choice of airfares and accommodation. If you can’t get enough of this Midwestern gem, book sweet Illinois holiday deals and roll through “The Prairie State”.


Guide to Exploring Chicago


Top Hotel Deals in Chicago

See all 1,635 properties in Chicago

Estimated price for 1 night/2 adults

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     

    Located in The Loop, this hotel is steps from Columbia College Chicago, Museum of Contemporary Photography, and Auditorium Building and Theatre. Fine Arts Building ...

    Congress Plaza HotelAU$182

    11 Aug - 12 Aug

    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago, IL
      4.0 out of 5.0
       
       

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

      Hyatt Regency ChicagoAU$266

      15 Aug - 16 Aug

      Travelodge by Wyndham Downtown Chicago

      Travelodge by Wyndham Downtown Chicago

      65 E Harrison St, Chicago, IL
        2.0 out of 5.0
         
         

        Located in The Loop, this hotel is steps from Lakefront Trail, Columbia College Chicago, and State Street. Buckingham Fountain and Grant Park are also within ...

        Travelodge by Wyndham Downtown ChicagoAU$158

        25 Jul - 26 Jul

        Hotel Essex Chicago

        Hotel Essex Chicago

        800 S Michigan Ave, Chicago, IL
          4.0 out of 5.0
           
           

          Located in The Loop, this hotel is within a 5-minute walk of Lakefront Trail, State Street, and Columbia College Chicago. Grant Park and Buckingham Fountain ...

          Hotel Essex ChicagoAU$196

          29 Jul - 30 Jul

          Central Loop Hotel

          Central Loop Hotel

          111 West Adams Street, Chicago, IL
            4.0 out of 5.0
             
             

            Located in The Loop, this boutique hotel is within a 5-minute walk of Chicago Board of Trade Building and State Street. Willis Tower and Skydeck Ledge are also ...

            Central Loop HotelAU$194

            28 Jul - 29 Jul

            Warwick Allerton - Chicago

            Warwick Allerton - Chicago

            701 North Michigan Avenue, Chicago, IL
              4.0 out of 5.0
               
               

              This family-friendly Chicago hotel is located in the entertainment district, just steps from Northwestern Memorial Hospital and Michigan Avenue. Chicago Water ...

              Warwick Allerton - ChicagoAU$189

              21 Jul - 22 Jul

              Kinzie Hotel

              Kinzie Hotel

              20 W Kinzie St, Chicago, IL
                4.0 out of 5.0
                 
                 

                Located in River North, this hotel is steps from House of Blues Chicago and State Street. Tribune Tower and Wrigley Building are also within 10 minutes. Grand ...

                Kinzie HotelAU$229

                11 Aug - 12 Aug

                The St. Clair Hotel – Magnificent Mile

                The St. Clair Hotel – Magnificent Mile

                162 East Ontario Street, Chicago, IL
                  2.5 out of 5.0
                   
                   

                  Located in Near North Side, this hotel is within 1 mi (2 km) of Navy Pier, Millennium Park, and Art Institute of Chicago. Cloud Gate and Grant Park are also ...

                  The St. Clair Hotel – Magnificent MileAU$178

                  21 Jul - 22 Jul

                  Top Deals on Flights to Chicago

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