CHICAGO
Explore Chicago: Top Activities, Neighborhood Gems, and Iconic Landmarks
By Jamie Dutton | June 18, 2025
You can eat very well in Chicago. You can get a drink in a 19th-century firehouse or on a rooftop overlooking a lake so big it might as well be an ocean. You can stand at the feet of a 110-ton silver bean or under the bones of a dinosaur named Máximo.
But the truth is, you don’t come to Chicago to check boxes off a brochure. You come because it’s loud, it’s contradictory, it smells a little like popcorn and hot asphalt, and somehow all of that is comforting. This is a city that refuses to be experienced passively.
So here it is: the best things to do in Chicago, none of them phoned in, all worth your time—even if you're just here for the weekend and mostly came for the pizza.
1. Millennium Park
FREE | MAP | WEBSITE | INSTAGRAM
Millennium Park is more than just a park—it's a selfie battleground, and Cloud Gate (lovingly dubbed "The Bean") is the ultimate prize. Every visitor tries to capture the perfect distorted reflection of the skyline and their faces, and it's amusing to watch people maneuver for the best angle. It’s also a great spot to enjoy some public art, relax by the Crown Fountain, or catch a concert at the Jay Pritzker Pavilion, which doubles as a giant stainless-steel band shell.
2. Art Institute of Chicago
TICKETS | MAP | WEBSITE | INSTAGRAM
No trip to Chicago is complete without visiting the Art Institute of Chicago. Home to Grant Wood’s "American Gothic" and George Seurat’s "A Sunday on La Grande Jatte," it's like stepping into an art history textbook, except no one's going to quiz you on the way out. I could spend hours wandering the impressionist galleries, losing myself in a Monet haze. If you’re into medieval armor or miniature rooms, they've got those too—because why not?
3. Wrigley Field
TICKETS | MAP | WEBSITE | INSTAGRAM
Even if you don't know a baseball from a basketball, a visit to Wrigley Field is essential. The stadium is a relic of old-time Americana, complete with ivy-covered outfield walls and hot dogs that require an immediate run around the bases just to burn off the calories. Catching a Cubs game here is less about the score and more about soaking in the atmosphere. It’s where you can truly experience the essence of Chicago sports culture—loud, proud, and never quite sober.
4. Willis Tower Skydeck
TICKETS | MAP | WEBSITE | INSTAGRAM
The building most of us still know as the Sears Tower, the Willis Tower Skydeck offers views that will make you question why you ever thought about conquering your fear of heights. The real thrill is "The Ledge," a glass box that extends out 4.3 feet from the 103rd floor, giving you the sensation of floating above the city. It's a surreal experience, assuming you can manage not to look down too long or scream loud enough to shatter the glass.
5. Navy Pier
TICKETS | MAP | WEBSITE | INSTAGRAM
Sure, it’s touristy, but Navy Pier has its charms. With a giant Ferris wheel, boat tours, and an endless supply of fried food, it’s like a carnival that got lost on its way to the Midwest and ended up on the shores of Lake Michigan. The Chicago Shakespeare Theater is here too, in case you need a little culture to balance out the funnel cakes. It’s the kind of place where you can spend the day pretending you’re on vacation, even if you’re only a few miles from home.
6. Museum of Contemporary Art
TICKETS | MAP | WEBSITE | INSTAGRAM
The Museum of Contemporary Art doesn’t care if you get it. That’s part of the fun. One gallery might be a floor-to-ceiling shrine to sneaker culture, another a looping video of someone trying to melt ice cubes with their breath. If you leave a little confused, that means you did it right. Bonus: It’s steps from the Mag Mile, so you can decompress afterward with a coffee and some light capitalism.
7. Music Box Theatre
TICKETS | MAP | WEBSITE | INSTAGRAM
This 1929 movie palace in Lakeview feels like it was designed by someone who once saw an Italian opera and a haunted castle and said, “Yes, that.” It screens everything from foreign indies to cult horror to 70mm epics, and the popcorn is actually good. Come for the velvet seats and star-painted ceiling. Stay for the crowd who actually claps after the credits.
8. The 606
FREE | MAP | WEBSITE | INSTAGRAM
Built on an old elevated rail line, the 606 is Chicago’s answer to the High Line, only with fewer influencers and better empanadas. It runs nearly three miles through Logan Square, Humboldt Park, and Wicker Park, and it’s ideal for a morning run, a dog walk, or just pretending you live here while you eavesdrop on people arguing about condo boards.
9. Chicago Architecture Center Boat Tour
TICKETS | MAP | WEBSITE | INSTAGRAM
Yes, it’s touristy. And yes, you should absolutely do it. The Chicago Architecture Center’s 90-minute boat tour is the only time it's acceptable to gawk at office buildings and whisper “Gothic Revival” like it means something. You’ll cruise the river with a docent who knows exactly how to make steel-frame construction sound scandalous. Bring sunglasses. And a sweater. The wind is not a metaphor.
10. White Sox Cheap Seats
TICKETS | MAP | WEBSITE | INSTAGRAM
Wrigley gets the love, but Guaranteed Rate Field (yes, that’s really the name) offers the kind of no-frills baseball experience that feels increasingly rare. The beer is cold, the hot dogs are aggressively mustardy, and the fans heckle like it’s a blood sport. If you want luxury boxes and ivy walls, go north. If you want to remember why baseball mattered to your dad, come here.
