This website uses cookies

We use cookies to ensure you have an easy, quick and reliable experience whilst using the Virgin Holidays website. By continuing to browse the site you are agreeing to our use of cookies. For more details, see our cookie policy.

Skip to main content Virgin holidays logo
  • Mon to Fri 9:00am - 5:00pm
  • Saturday 9:00am - 5:00pm
  • Sunday 10:00am - 6:00pm

Things to see and do in Chicago

Chicago experiences

More about Chicago

Chicago was once home to a slew of gangsters during the 1920s and 1930s. They were the baddest of the bad, yet also the champions of the people particularly during the Prohibition era. Some of the most notorious hangouts for gangsters like 
Al Capone, John Dillinger and Bugs Moran can still be found in the city.

Catch a game of baseball at the iconic Wrigley Field. Home to the Chicago Cubs since 1916, you can see the ivy-coated outfield wall and the hand-operated scoreboard, while cracking peanuts in the stands.

Things to see in Chicago

Chicago blues started as street - based music form in back alley blues clubs located on the south side of Chicago. Even today, Chicago stays close to its roots by annually hosting the largest free blues festival in the world.

Chicago Blues

The story of the USA reveals itself, mile by mile along the Historic Route 66. Known as the Mother Road, the route runs from Chicago to Los Angeles and is peppered with classic diners, drive-in theatres, and odd roadside attractions along the way – a true representation of American kitsch.

Route 66 in Chicago