5 Things To Do With a Weekend in Chicago

The third-largest city in the U.S. and the largest city by far in the Midwest, Chicago over the past few years has seen tremendous growth in its popularity as a tourist destination. Whether it's the city's status as an airport hub, its location on Lake Michigan, or its numerous references in popular culture, there's obviously something about Chicago that has captured people’s imagination.

If you are thinking of adding Chicago to a U.S. itinerary (or perhaps just planning a long weekend getaway), here are five things you shouldn't miss in the Windy City:

Ascend a tower

Chicago is known for its old-and-new mix of architecture, and for its recognizable skyline. While you're in the city, you should definitely get a view of it from above. You can either visit the Willis Tower (formerly the Sears Tower) and its Skydeck, or you can go up to the Observatory at the John Hancock Tower. Both offer great views, though the Hancock Observatory usually has shorter lines.

See some improv

Believe it or not, Chicago has one of the biggest improvised theater scenes in the United States – the comedy form was actually born in this city. Many popular comedians (like Dan Aykroyd, Bill Murray, Mike Myers, Tina Fey, Stephen Colbert, Jane Lynch, and Steve Carell, just to name a few) got their start at The Second City, a training center and performance venue that opened in Chicago in the late 1950s. Today you can catch improv shows all over Chicago, including at Second City, i.O. (the second-most-popular sketch comedy school and venue), ComedySportz, and The Playground Theater, among others. It's a great way to spend a Friday night.

Eat deep dish pizza

No trip to Chicago would be complete without having some deep dish pizza – yet another Chicago invention. This thick-crusted pizza piled high with cheese and sauce is a must-eat in the Windy City. Where you get it, however, is a matter of debate. You can try deep dish from Pizzeria Uno (where it's said to have been invented), Gino's East, Pizano's, Giordano's, Lou Malnati's, or Pequod's and be guaranteed a quality pie. Which one is “best” will be up for you to decide!

Go to a museum

There are some great museums in Chicago to suit all interests. Learn about history (including dinosaurs!) at the Field Museum, get your science on at the interactive Museum of Science and Industry, or practice some art appreciation at the Art Institute of Chicago. You can also visit the Shedd Aquarium and the Adler Planetarium, which are located on “Museum Campus” along with the Field Museum.

Visit a park

If you're looking for a nice place to relax or perhaps just enjoy some greenery, head to one of Chicago's more than 550 parks (some of which even include beaches on Lake Michigan!). Parks that are really worth visiting include Lincoln Park (the largest in Chicago and also home to the Lincoln Park Zoo), Grant Park (where you'll find the impressive Buckingham Fountain along with great views of the Chicago skyline) and Millennium Park (home to the famous “Bean” sculpture). All of them come alive on sunny afternoons in the city.

Note: Available plans and coverages may have changed since this blog was published.