Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

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 1,475 properties in Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
    4.0 out of 5.0
     
     

    This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

    Palmer House a Hilton HotelAU$121

    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago
      4.0 out of 5.0
       
       

      This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

      Hyatt Regency ChicagoAU$147

      Embassy Suites Chicago Downtown Magnificent Mile

      Embassy Suites Chicago Downtown Magnificent Mile

      511 North Columbus Drive, Chicago
        4.0 out of 5.0
         
         

        The Embassy Suites Chicago Downtown Magnificent Mile offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, ...

        Embassy Suites Chicago Downtown Magnificent MileAU$138

        Freehand Chicago

        Freehand Chicago

        19 East Ohio Street, Chicago
          3.5 out of 5.0
           
           

          Located in River North, this hotel is within 6 mi (10 km) of Chinese Consulate, Holy Name Cathedral, and Museum of Contemporary Art. Water Tower Place and Ann ...

          Freehand ChicagoAU$97

          The St. Clair Hotel – Magnificent Mile

          The St. Clair Hotel – Magnificent Mile

          162 East Ontario Street, Chicago
            2.5 out of 5.0
             
             

            The hotel is a half-block from the Magnificent Mile and an 8-minute walk from Grand/State Metro Station. Many attractions are within a 15-minute walk, including ...

            The St. Clair Hotel – Magnificent MileAU$92

            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago
              3.5 out of 5.0
               
               

              Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

              Congress Plaza HotelAU$100

              Hyatt Centric Chicago Magnificent Mile

              Hyatt Centric Chicago Magnificent Mile

              633 N Saint Clair St, Chicago
                4.0 out of 5.0
                 
                 

                This smoke-free 17-story hotel is 1 block from North Michigan Avenue's boutique and specialty stores, 3 blocks from Lake Michigan, 6 blocks from the State & ...

                Hyatt Centric Chicago Magnificent MileAU$169

                River Hotel

                River Hotel

                75 East Wacker Drive, Chicago
                  4.0 out of 5.0
                   
                   

                  Located in The Loop, this hotel is within a 5-minute walk of Chicago Riverwalk and Chicago Theatre. Michigan Avenue and House of Blues Chicago are also within ...

                  River HotelAU$95