Top 10 Things to Do in Chicago

Welcome to the Windy City! With its stunning architecture, world-class museums, incredible food scene, and scenic lakefront, Chicago is one of the most exciting destinations in the United States. Whether you are planning a quick weekend getaway or a week-long vacation, there is no shortage of things to see and do. If you are visiting for the first time, here are the top 10 things to do in Chicago to help you plan an unforgettable trip.

1. Snap a Photo at Millennium Park

No trip to Chicago is complete without visiting Millennium Park. Located in the heart of downtown, this vibrant public space is home to the iconic Cloud Gate sculpture, affectionately known as “The Bean.” The mirror-like surface reflects the stunning city skyline, making it the ultimate spot for a vacation selfie.
Tip: Visit early in the morning to beat the crowds and get a clear photo without waiting in line.

2. Walk the Chicago Riverwalk

The Chicago Riverwalk is a picturesque, pedestrian-friendly path carved right alongside the Chicago River. Lined with outdoor cafes, bars, and public art, it is the perfect place for a leisurely stroll. You can watch boats glide past historic bridges or rent a kayak to paddle down the river yourself.
Tip: Grab a coffee or a snack and sit on one of the public seating areas to watch the sunset behind the skyscrapers.

3. Step Out on the Ledge at Willis Tower

For the ultimate view of the city, head up to the Skydeck on the 103rd floor of the Willis Tower—formerly known as the Sears Tower. On a clear day, you can see across four different states. If you are feeling brave, step out onto “The Ledge,” a glass balcony that extends four feet outside the building, offering a straight-down view of the street far below.
Tip: Purchase your tickets online in advance to secure your preferred time slot and avoid long lines at the box office.

4. Stroll Along Navy Pier

Stretch out along the shoreline of Lake Michigan, Navy Pier is a historic landmark packed with entertainment, dining, and family-friendly attractions. Take a ride on the giant Centennial Wheel for panoramic views of the lake and the skyline, or catch a performance at the Chicago Shakespeare Theater.
Tip: Navy Pier hosts spectacular fireworks displays during the summer months, so check the schedule before you go.

5. Explore the Art Institute of Chicago

Consistently ranked among the best museums in the world, the Art Institute of Chicago houses an enormous collection spanning thousands of years of human creativity. Here, you can view famous masterpieces like Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte.
Tip: The museum is massive; grab a map at the entrance and pick two or three specific galleries to focus on so you do not get overwhelmed.

6. Dive Deep at the Shedd Aquarium

Located on the city’s stunning Museum Campus, the Shedd Aquarium is home to thousands of aquatic animals, including dolphins, beluga whales, penguins, and sharks. It is a fantastic destination for travelers of all ages, offering interactive exhibits and incredible views of Lake Michigan from the back patio.
Tip: Check the daily schedule upon arrival to catch the animal presentations and training sessions.

7. Indulge in Authentic Chicago Deep-Dish Pizza

You cannot visit Chicago without trying its legendary deep-dish pizza. Known for its buttery, pie-like crust, chunky tomato sauce, and layers of melted cheese, it is a hearty meal that you will not forget. Iconic spots like Lou Malnati’s, Giordano’s, and Pequod’s are local favorites.
Tip: Deep-dish pizza takes about 30 to 45 minutes to bake, so order an appetizer or a house salad while you wait.

8. Shop and Sightsee on the Magnificent Mile

Stretching along Michigan Avenue, the Magnificent Mile is Chicago’s premier commercial district. It features historic water towers, upscale department stores, trendy boutiques, and remarkable architectural landmarks. Even if you aren’t planning on shopping, window shopping and admiring the historic buildings make for a great afternoon walk.
Tip: Keep an eye up—some of the most beautiful architectural details are found on the upper stories of the buildings.

9. Relax in Lincoln Park

Escape the hustle and bustle of downtown by heading north to Lincoln Park. This expansive green space runs along Lake Michigan and features tranquil walking paths, sandy beaches, and sports fields. Best of all, the historic Lincoln Park Zoo is located right inside the park and offers free admission every day of the year.
Tip: Combine your park visit with a walk through the charming surrounding neighborhood to admire the classic brownstone homes.

10. Catch a Game at Wrigley Field

Baseball fan or not, taking in a game at Wrigley Field is an authentic Chicago experience. As one of the oldest and most historic ballparks in America, it boasts classic ivy-covered brick outfield walls and a neighborhood vibe unlike any other stadium in the country.
Tip: If you can’t get tickets to a game, you can still book a historical tour of the stadium during the off-season or non-game days.

Planning Your Trip

Best Time to Visit

The best time to visit Chicago is during the shoulder seasons of late spring (April to May) and early autumn (September to October), when the weather is pleasant and outdoor festivals are in full swing. Summer brings gorgeous lakefront weather and endless outdoor events, though it is also the peak tourist season. Winter can be quite cold and windy, but it offers fewer crowds and holiday charm.

Getting Around

Chicago is an exceptionally walkable city with a fantastic public transportation system. The CTA (Chicago Transit Authority) operates an extensive network of “L” trains and buses that can easily get you to almost any attraction. Renting a car is generally unnecessary and can be expensive due to parking fees.

Enjoying the City on a Budget

You don’t need to spend a fortune to enjoy Chicago. Take advantage of free attractions like Millennium Park, the Lincoln Park Zoo, and the Chicago Cultural Center. You can also explore the city’s stunning architecture simply by walking around downtown or taking an affordable ride on a public water taxi.

Pack Your Bags

From the breathtaking views at the top of the Willis Tower to a relaxing stroll along the Riverwalk, Chicago offers a perfect blend of culture, history, and urban adventure. Start planning your itinerary today, bring a comfortable pair of walking shoes, and get ready to fall in love with the Windy City!