Trip Ideas

Must-See

CHICAGO

Even the locals are surprised by the sheer number of things to do in Chicago. The endless shopping, stunning architecture, renowned museums, lively nightlife—the list goes on and on. So how does someone come up with a plan to experience this world-class city? Start with a few must-see sites that define Chicago, and go from there.

Festivals & Events

Find year-round events that spill into Chicago’s streets and parks.

Chicago hosts the Chicago Air and Water Show, Taste of Chicago and other marquee events throughout the year. But summer is when festivals hit their stride, taking over a different street each weekend in Chicago’s neighborhoods.

The Museum Campus

Go back in time, under the sea and to another galaxy.

  • The Field Museum
    The Field Museum

    Regarded as one of America’s premiere natural history museums, the Field features everything from ancient Egyptian tombs to man-eating lions from the 19th century. But the biggest star here is Sue, the largest and most complete T. rex skeleton ever unearthed.

    Go Here
  • Shedd Aquarium
    Shedd Aquarium

    Next door to the Field Museum is the most visited aquarium in the country, home to more than 1,500 water creatures. Here you’ll find sharks, penguins, beluga whales and the ever-popular Pacific white-sided dolphins that perform their aquatic acrobatics in the Oceanarium exhibit.

    Go Here
  • Adler Planetarium
    Adler Planetarium

    Up the street you can explore the universe at America’s first planetarium. Discover hands-on exhibits and artifacts, including a fully restored Gemini 12 capsule. Or visit the world’s most advanced digital theater for an immersive journey deep into space.

    Go Here

Chicago Blues

See living legends play the blues
in the city where it all began.

To truly hear the blues, you have to experience it live. And there’s no better place to experience this uniquely American art form than in Chicago, where familiar chords and an unmistakably urban rhythm still echo through the clubs. Today, living legends like Buddy Guy still take the stage to give electric performances here you won’t soon forget.

SEE CLUBS

Step into a Skyline

Gaze out a 103rd-story window, then walk through it.

Ever wonder what it’s like to walk on air? Well wonder no more. High atop the Willis Tower (formerly the Sears Tower) you’ll find the Ledge, a glass balcony jutting out from America’s tallest building. Now you can gaze out on endless views and stare 1,353 feet straight down to the street below.

GO HERE

Chicago’s Theatre Scene

From legendary improv to over-the-top Broadway productions.

  • Broadway in Chicago
    Broadway in Chicago

    Chicago’s bustling theatre district features Broadway productions performed at the same caliber you’ll find anywhere. Shows often make their world premiere in Chicago giving you a chance to be among the first to see the next big thing everyone will soon be talking about.

    See Theatres
  • Regional Theatre
    Regional Theatre

    For a taste of Chicago’s homegrown theatre scene, head to intimate venues like the Goodman Theatre and Steppenwolf, two of the many ensemble houses in Chicago bringing groundbreaking productions to America’s theatre scene.

    See Theatres
  • Improv & Sketch Comedy
    Improv & Sketch Comedy

    Some of the biggest names in comedy got their start on the improv stages of Chicago. From Second City and the Annoyance Theatre to IO and ComedySportz, there are plenty of ways to experience Chicago-style sketch and improv comedy every night of the week.

    See Theatres

A Day in the Park

Explore the crown jewel of Chicago’s outdoor spaces.

Millennium Park has fast become one of Chicago’s premiere attractions, perfectly situated steps from Michigan Avenue. Here you can play with the art, dine al fresco, stroll through manicured gardens and go ice skating during winter. In the evening, spread a blanket on the lawn and catch free performances at the stunning Pritzker Pavilion.

GO HERE

Guided Tours

Experience the side of Chicago that interests you most.

Hop aboard everything from boats to trolleys during guided tours that give you the inside scoop on Chicago architecture, blues, pizza and more.

SEE TOURS
Explore More

See all the attractions of this world-class city.

Expand your Chicago must-see list with hundreds of attractions that include everything from award-winning cuisine to a shopper’s paradise on the Magnificent Mile.

From our blog

Get a firsthand look from our Mile Markers
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Chicago via Enjoy Illinois Blog

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