Things to Do in Chicago in 4 Days: Itinerary, Top Attractions, Deep-Dish Pizza & More
- Bianca Paola Gonzalez
- Oct 16
- 3 min read
To read in Spanish click here.
Planning a trip to Chicago? Today I’m sharing a simple guide of things to do in Chicago on a 4-Day trip.
The windy city has amazing views, cool museums, and of course, deep-dish pizza. If you’re planning a visit here, I hope this guide gives you a good starting point.
Day 1: Iconic Views & River Vibes
360 CHICAGO Observation Deck
Start your trip with a stunning view at the 360 CHICAGO Observation Deck. It’s on the 94th floor of the John Hancock Center and lets you look out over the city (and lake) from 1,000 feet up.
If you’re feeling adventurous, you can try the TILT — it’s a moving glass platform that leans you out over Michigan Avenue. I missed it when I went, but it looked fun…and wild! I wonder what my reaction would’ve been. 🤭
Chicago Riverwalk Boat Tour
After taking in the views, head down to the Chicago Riverwalk for a chill stroll along the water. It’s a 1.25-mile path with cool art, waterfront cafés, and architectural boat tours. I’d recommend doing the tour at sunset, but honestly, it’s beautiful anytime. You get a fresh perspective of Chicago’s amazing architecture and skyline.
Day 2: Parks, Skydecks & Pizza
Cloud Gate (aka “The Bean”) & Millennium Park
No trip to Chicago is complete without seeing The Bean. It’s a work of art designed to distort and reflect the city's skylines so it attracts many tourists. Snapping a selfie is a must. Also, feel free to wander through Millennium Park. You can check out the Crown Fountain and the Jay Pritzker Pavilion while you’re at it.
Willis Tower Skydeck
Looking for more views? Go over to Willis Tower (formerly the Sears Tower) for the Skydeck and step onto “The Ledge,” which is a glass box that juts out over the city. I was a little nervous stepping in, not going to lie, but the view really is breathtaking.
Try Chicago’s Deep-Dish Pizza
After all that walking and sightseeing, reward yourself with some deep-dish pizza, a classic Chicago dish. Lou Malnati’s, Giordano’s, or Pequod’s are all solid choices.
Day 3: Museums & Aquarium
Shedd Aquarium
Start your day at the Shedd Aquarium, home to over 32,000 animals from across the globe. From beluga whales to colorful reef fish, it’s popular for family visits.
Field Museum
Next door is the legendary Field Museum. Don’t miss Sue, the most complete Tyrannosaurus rex skeleton ever found, and the Ancient Egypt exhibit. A visit to the Field Museum is extensive. On average, people spend 3 to 4 hours exploring it. Plan accordingly— to your time, interests, and your plans for the rest of the day.
Adler Planetarium
Wrap up your museum day at the Adler Planetarium. With immersive sky shows and interactive exhibits, it’s both inspiring and educational. I truly enjoyed my time here. Also, the lakeside location offers amazing photo opportunities.
Day 4: Shopping, Coffee & Skyline Views
Magnificent Mile
Time to shop (or window-shop) along Michigan Avenue! The Magnificent Mile has all kinds of stores, from high-end boutiques to cool souvenir spots. It’s perfect for people-watching, too, which is something I’ve been appreciating when I travel.
Starbucks Reserve Roastery
Take a break at the Starbucks Reserve Roastery, the largest Starbucks in the world. It’s got five floors of coffee goodness, pastries, plus cocktails. If you’re into coffee, you have to try their Espresso Martini!
Navy Pier
Make your way to Navy Pier, where you can enjoy rides (like the Centennial Wheel, for more views), public art, live performances, and lakefront views.
London House Rooftop Bar
Finish off your trip with cocktails and a beautiful view at the London House Rooftop Bar. Overlooking the Chicago River and the Wrigley Building, it’s a great spot to toast to an unforgettable time in the city. Make sure you make reservations online, though.
Chicago truly has something for everyone— whether you're into architecture, food, science, or just want to soak in the skyline. My second time in the city was even more exciting because I got to see my favorite K-pop group perform, which led me to explore Chinatown and K-pop Nara.
Four days might not be enough to see everything, but this itinerary of things to do in Chicago hits the highlights and gives you a well-rounded experience of the city.
If you’ve been to Chicago, let me know in the comments what other places I should visit on my next trip.
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