14 Fun Things to Do in Chicago for First-time Visitors, Chicago, Illinois

Thinking about a trip to Chicago? You’re in for incredible food, beautiful lake views, and that lively city pace that makes it hard to sit still.

From taking an architecture cruise on the river to catching a show at The Second City or digging into a slice of deep dish, Chicago delivers a little bit of everything.

I’ve been lucky enough to visit Chicago many times over the years, and am sharing some of my favorite things to do in Chicago in today’s post.

Start your visit at Millennium Park, right in the heart of downtown. You can’t miss Cloud Gate, better known as The Bean; its mirror-like surface reflects the city’s skyline and everyone who walks by, making it one of the most photographed spots in the Midwest. 

And while you’re here, don’t just rush through. Take time to walk around the Jay Pritzker Pavilion, and cool off by the interactive Crown Fountain in the summer.

Right next to Millennium Park sits one of the world’s greatest museums – the Art Institute of Chicago. You’ll see major works here from Van Gogh to Seurat, along with an incredible range of other iconic pieces. ...... (follow the instructions below for accessing the rest of this article).