Over the past couple of years, Chicago—aka the Windy City—has seen record-breaking numbers of tourists, and honestly? It’s no surprise at all. This city is bursting with energy and fun, boasting amazing food, countless parks, and a ton of unmissable attractions.
Planning a trip to Chicago soon? Keep scrolling to discover my top 10 must-do activities that’ll make your Windy City adventure unforgettable!
1. Millennium Park & The Bean (Cloud Gate)
Let’s be real—your Chicago trip isn’t complete without a stop at Millennium Park! And the star of the show? Cloud Gate, the iconic sculpture locals affectionately call “The Bean.” Don’t forget to snap a photo (or five) here—it’s basically a Chicago rite of passage.
Created by artist Anish Kapoor, this shiny, mirrored structure is way more fun than just a photo op. Take a few minutes to walk around and even under it—you’ll love how it reflects the city skyline in the most whimsical way. While you’re exploring the park, make sure to check out the Crown Fountain too. The giant digital faces projected on the towers spurt water from their mouths at intervals, and it’s always a hit with both kids and adults.
Pro tip: After visiting The Bean, duck across the street to the Chicago Cultural Center—you won’t want to miss the stunning Tiffany Dome inside!
2. Willis Tower SkyDeck Chicago
For sky-high views of the city, head to the SkyDeck at the top of Willis Tower (formerly the Sears Tower). The observatory offers a breathtaking 360-degree panorama of Chicago, and it’s the perfect spot to get a sense of the city’s layout.
Feeling adventurous? Step out onto The Ledge—a glass floor that extends 4 feet over the building’s edge, 1,353 feet above the ground! The support system is completely invisible, making it feel like you’re floating in mid-air. Trust me, the view is unparalleled. Tickets for The Ledge are $24 and include access to the museum exhibits, so it’s totally worth the splurge.
3. Navy Pier
I know some travelers write off Navy Pier as a “tourist trap,” but hear me out—if you’re visiting Chicago for the first time, it’s absolutely worth exploring. This historic landmark sits right on the shores of Lake Michigan, stretching over 3,000 feet long with parks, shops, restaurants, and attractions galore.
Built by renowned architect Charles Sumner Frost, Navy Pier first opened in 1916 as Municipal Pier before being renamed in 1927 to honor WWII Navy veterans. While you’re here, check out the Chicago Children’s Museum (great for families!) or catch a show at the Chicago Shakespeare Theater. Even if you just wander around and take in the lake views, it’s a lovely way to spend an afternoon.
4. Architecture Cruise
Chicago is a paradise for architecture lovers—so many famous buildings call this city home, and some of the world’s most legendary architects got their start here. The best way to appreciate Chicago’s skyline? An architecture cruise!
Sit back, relax, and let an expert guide point out the unique features and fascinating history of the city’s buildings. With over 50 skyscrapers dotting the skyline, you’ll learn so much about the “Chicago School” of architecture and how this city shaped the modern skyline. It’s a super chill and educational activity—perfect for a sunny day on the water.
5. The Art Institute of Chicago
Located on Michigan Avenue, the Art Institute of Chicago is a must-visit for any art lover (or anyone who appreciates beautiful buildings!). You can’t miss the iconic lion statues flanking the entrance—sculpted by Edward Kenny, they’re basically Chicago’s mascots.
Inside, the collection is incredible. If you’re a fan of Impressionism, you’ll be in heaven—don’t miss George Seurat’s masterpiece “Sunday on the Island of La Grande Jatte.” The museum also houses works by Georgia O’Keeffe, Marc Chagall, and Henri Matisse, so there’s something for every art taste. Plan to spend a few hours here—you could easily get lost in the galleries!
6. Eat Your Way Through Chicago (Foodie’s Guide)
Let’s talk about the real star of Chicago: the food! This city is a foodie’s dream, with so many iconic dishes you have to try. Start your day right at Cupitol Coffee & Eatery—named one of USA Today’s 10 Best Coffee and Breakfast Shops, it’s the perfect spot for a cozy morning bite (trust me, their pastries are *chef’s kiss*).
Now, let’s get to the classics: Pizza. Locals swear by thin-crust pizza, but you can’t leave Chicago without trying deep-dish at least once. My go-to spot? Lou Malnati’s—their buttery crust and gooey cheese are unforgettable. Next, head to Little Italy/University Village for an Italian beef sandwich (get it “dipped” for extra flavor!) and finish with a refreshing Italian ice. And of course, a Chicago dog is non-negotiable—Superdawg is a fun retro spot that serves up the perfect Chicago-style dog with all the fixings.
Pro tip: Keep a travel journal or use a food-tracking app to log all these amazing spots—you’ll want to remember them for future trips!
7. Wrigley Field
Chicagoans are serious about their sports, and Wrigley Field is a sacred place for baseball fans. Even if you’re not a die-hard sports buff, you’ll appreciate the history and charm of this iconic ballpark.
If you can’t catch a game (or you’re visiting in the off-season), book a guided tour! For around $25, you’ll get a 90-minute tour led by a knowledgeable guide who’ll share all kinds of fun facts about the stadium’s history. A quick heads-up: Parking in Chicago is tough, and the Wrigley Field area is no exception. Skip the hassle and take the “L” train to the Addison stop—it’s way easier!
8. The 606
Looking for a unique outdoor activity? Check out The 606—an elevated recreational trail that’s perfect for urban hiking, biking, or just a leisurely stroll. Stretching almost 3 miles long, it’s open from 6 am to 11 pm, and yes—dogs are welcome too (great for pet parents!).
The trail follows an old abandoned rail line that was elevated in the late 1800s to eliminate dangerous ground-level crossings. It opened as a recreational trail in the early 2000s, and now it’s lined with greenery, public art, and lots of fun bars and restaurants. It’s a fantastic way to explore a more local side of Chicago and get some fresh air.
9. Shedd Aquarium
Shedd Aquarium is one of the largest aquariums in the world, and it’s a total highlight for families (and anyone who loves marine life!). Here, you can see penguins waddling around, sharks gliding through the water, and even whales. For an extra special experience, book a behind-the-scenes tour or an animal encounter (additional fees apply)—it’s a great way to get up close and personal with the sea creatures.
Admission is around $40 for adults and $30 for children, and I recommend planning to spend at least half a day here to make the most of your visit. Pro tip: Get a CityPASS or Go Chicago Card—you’ll get a free ticket to the aquarium, which saves you some cash!
Shedd Aquarium is located in Grant Park, right near the Field Museum and Adler Planetarium—so you can easily make a day of it by visiting multiple attractions.
10. Grant Park
Last but definitely not least: Grant Park. This 300-acre green space starts at the eastern edge of the Loop and stretches down toward the South Side, right next to Millennium Park. It’s the perfect spot to relax, picnic, or take in the city views after a busy day of sightseeing.
Grant Park is home to the Field Museum, Shedd Aquarium, and Adler Planetarium, so it’s a hub for attractions. But the real star here is Buckingham Fountain—one of the largest fountains in the world! From May to October, every hour there’s a 20-minute water show where jets shoot water up to 150 feet into the air. Just note that the fountain closes for the winter, so plan accordingly.
Ready to Explore the Windy City?
Now that you have my list of the 10 must-do Chicago activities, what are you waiting for? It’s time to pack your bags and head to the Windy City!
Stand atop The Ledge for jaw-dropping views, indulge in all the iconic Chicago eats, wander Navy Pier, catch a show, explore the Shedd Aquarium, and relax in Grant Park. Trust me, Chicago is a city that’ll steal your heart—and you’ll already be planning your next trip before you leave.
