Iconic Chicago: the city's most popular things to see and do

Music, art, food, culture, or sports ... whatever your interests are, Chicago's got amazing things for you to see and do. The city’s excellent public transit system, Divvy bike share program, and accessible lakefront trail makes it easy to get from one part of Chicago to the other. Plus there are taxis and Uber drivers everywhere.

Since the cold, snowy Chicago winters can test even the hardiest humans, the best time to visit the city is in the spring, summer and fall. That way you can see Chicago’s many attractions is by boat. The Chicago Architecture Foundation’s River Cruise takes visitors along the Chicago River while knowledgeable docents share the history of Chicago, its architecture and how it became one of the world's most important crossroads of today.

Using Chicago’s Lakefront Trail, it’s easily possible to stop along the route and view the Monet paintings at The Art Institute or take a picture with The Bean at Millennium Park.

For a different kind of attraction, see a show at Second City, the same comedy troupe that launched the careers of comedians including Gilda Ratner, John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others.

An ape house, a birdhouse and a working model of a five-acre Midwestern farm are just a few examples of what makes this zoo special. Founded in 1868 and known as America's oldest free public zoo, the Lincoln Park Zoo still manages to charge no...  Read More

This downtown pier that extends into Lake Michigan was once used by the military. Today, it's Chicago's largest tourist hub. You can just walk up and down the pier, taking in the gorgeous skyline and lake views. Or you can visit the excellent...  Read More

A highlight of any trip to Chicago, this museum is home to one of the best and most diverse art collections in the world. People are drawn first to the vast Impressionist collection, including the world's largest group of Monet paintings. But...  Read More

This eye-catching, twelve-sided building includes two sky theaters, one of which was the first planetarium in the western hemisphere. The theaters depict the night sky and allow visitors an up-close look at distant planets, moons and galaxies....  Read More

After 40 seconds in John Hancock's elevator, visitors are transported 1,000 feet above Chicago. From there, the city's third-largest building offers views that stretch out to 80 miles on a clear day. Food and drink are available in the...  Read More

Wrigley Field

This century-old ballpark is home to the Chicago Cubs, who haven't won a World Series in more than 100 years (but 2016 could be the year!). The party neighborhood around it is known as "Wrigleyville," full of restaurants and bars. The ballpark...  Read More

Second City
Photo courtesy of Photo courtesy of Choose Chicago

The world's premier comedy troupe, The Second City has launched some of the biggest names in the business, including Gilda Radner, John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others. So it's...  Read More

Millennium Park is Chicago's crown jewel. Summertime means a stellar line-up of concerts at Jay Pritzker Pavilion (during the day, on most Tuesdays through Fridays, the Grant Park Orchestra and Chorus can be heard for free in the Pavilion as...  Read More

Chicago Architecture Foundation River Cruise
Photo courtesy of Photo courtesy of Choose Chicago

Seeing Chicago's architectural beauty from the decks of a river cruiser is a must for both locals and visitors. One of the city's most unique tours, the CAF River Cruise takes visitors along the north and south shores of the lake. Guests will...  Read More

Chicago Lakefront Trail
Photo courtesy of Photo by Jamie Bartosch

With skyscrapers on one side and the lake on the other, this 18.5-mile walking, running and biking path is one of the city's most scenic places. The paved, linear path runs along Lake Michigan, stretching from the far north part of the city to...  Read More


Meet Jamie Bartosch

Jamie Bartosch is a lifelong Chicagoan who thinks her hometown is the greatest city in the world. She is an award-winning newspaper reporter, a freelance travel writer, and the mother of two great kids.