Things to Do Chicago


Adventurous tourists and actively creative Chicagoans alike find unique activities throughout the city. There’s no reason to go to the Navy Pier trap or another museum if you can experience the real, local events that Chicago has to offer. Whether you’re taking a family trip or a date night out into the city, the Windy City offers plenty of options for fun.

Street Festivals

Come summer, street festivals become a regular occurrence on the weekends. May through September are booked with neighborhood fests that never cost more than $5, and always feature good food, loud music and friendly people. Some of the top fests around town are Do Division, Wicker Park Fest, Renegade Craft Fair and Metronome Celebration. You can even bring your dog to these events, too.

Bicycle Trips

There aren’t many hills in Illinois, making Chicago a very bike-friendly area. With all of the marked bike lanes throughout the city, bicycling in the Windy City isn’t just an activity but a cultural phenomenon. The last Friday night of every month is Critical Mass, where hundreds to thousands of bicyclists take a group ride through the streets in protest of oil. If you want to avoid cars altogether, ride along the lakefront trail at a more leisurely pace.

Explore the Parks

Green spaces are everywhere in Chicago, and each park has unique aspects that make it beautiful. Lincoln Park has a free zoo, Garfield Park boasts a renowned conservatory, and Humboldt Park features stunning lagoons that almost look as if they were stolen from the Irish countryside. Whether you want to grill, toss around flying discs or just take an enjoyable stroll away from the skyscrapers, Chicago’s parks are a marvel of natural beauty to behold.

Architecture Tour

Art enthusiasts quickly recognize Chicago as a cultural hub of American design and architecture. Sign up for the Chicago Architecture Foundation tours to get an educational look at the breathtaking buildings of the Windy City, or simply take a walk downtown and enjoy the sights. You may even want to head out to Oak Park, just west of downtown, to see Frank Lloyd Wright’s historic home and studio.

Fireworks Nights

Head down to the lakefront throughout the summertime for massive fireworks displays. The occasion–simply being the city of Chicago, there’s always reason to celebrate life. And during the winter months, champagne and fireworks events are held at the Chicago River. Bundle up for that one, and take your date to a warm restaurant afterward.

About this Author

Arlen Hershey has been writing science curriculum for informal science education organizations since 2006. She has written for Experiencia and Sea World. She has a bachelor’s degree in biology from the University of Illinois.