Chicago blends historic charm, modern attractions, and a food scene that could keep you busy for weeks. From iconic architecture to deep-dish pizza, the city packs a lot into a relatively walkable area. Whether you’re visiting for a quick weekend or a longer stay, you’ll find plenty that makes the trip memorable.
Here is a list of 17 things to do on your first visit to Chicago that showcase its most iconic sights, flavors, and experiences.
Millennium Park
Home to the famous Cloud Gate sculpture—often called ‘The Bean’—Millennium Park is a staple stop for newcomers. The polished steel surface creates a fun, distorted reflection of the skyline and surrounding crowds. Beyond the sculpture, the park’s open green space and art installations make it a pleasant place to wander.
Seasonal events like outdoor concerts and ice skating in winter give it year-round appeal. It’s also conveniently located near other attractions so that you can plan multiple stops in one go.
Willis Tower Skydeck
The Willis Tower, still referred to by many as the Sears Tower, remains one of Chicago’s most recognizable landmarks. Visitors can step onto The Ledge, a glass balcony extending 4 feet out from the 103rd floor, for unmatched city views. On clear days, you can see up to 50 miles across four states.
The feeling of standing on transparent flooring that is high above the street is both thrilling and slightly surreal. It’s one of those experiences that sticks in your memory long after the trip ends.
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Navy Pier
Stretching over 3,000 feet into Lake Michigan, Navy Pier combines entertainment, dining, and lakefront views. You’ll find a Ferris wheel offering panoramic cityscapes, seasonal fireworks, and theaters for live performances. Walking the pier gives you a sense of Chicago’s maritime character and its connection to the Great Lakes.
The mix of attractions makes it a convenient stop for families, couples, or solo travelers. Even just sitting with a coffee while watching boats pass can be a highlight.
Chicago Riverwalk
The Chicago Riverwalk transforms a stretch of the city’s riverbank into a lively pedestrian zone. Cafés, public art, and small piers offer plenty of reasons to linger along the water. The architecture surrounding the river is some of the most distinctive in the country, with styles ranging from Art Deco to sleek glass towers.
Boat tours often depart from this area, giving you another way to experience the city’s skyline. At sunset, the light reflecting off the buildings and water creates a striking scene.
Art Institute of Chicago
One of the oldest and largest art museums in the U.S., the Art Institute houses an impressive collection from ancient artifacts to modern masterpieces. Its galleries feature works by Monet, Van Gogh, and Grant Wood, among others. The museum’s iconic bronze lion statues at the entrance have become a recognizable symbol of the city.
It’s easy to lose track of time here, with entire wings dedicated to different periods and regions. A well-placed bench in a quiet gallery can be as memorable as the art itself.
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Lincoln Park Zoo
Free to enter and open every day of the year, Lincoln Park Zoo offers an easygoing escape from the urban setting. Its compact size makes it ideal for a few hours of strolling without feeling rushed. The zoo’s historic buildings, lush landscaping, and variety of animals give it a charming, old-world feel.
From big cats to penguins, the exhibits are thoughtfully designed to offer close-up viewing without overcrowding. Being right next to the lakefront path makes it easy to combine with other nearby attractions.
Shedd Aquarium
The Shedd Aquarium’s vast collection of marine life includes everything from colorful reef fish to beluga whales. Its exhibits are designed to transport visitors to underwater environments across the globe. The Caribbean Reef, located right in the rotunda, is a favorite starting point for many guests.
Special encounters, like behind-the-scenes tours, give an even deeper appreciation for the animals and their habitats. The building’s lakefront location also offers postcard-worthy views of the skyline.
Field Museum
Best known for housing Sue, the most complete Tyrannosaurus rex skeleton ever discovered, the Field Museum covers millions of years of history. Its exhibits range from ancient Egyptian artifacts to detailed dioramas of animal habitats. The building’s grand architecture adds to the sense of discovery as you move from one gallery to another.
Interactive displays and rotating exhibits keep repeat visits interesting. It’s a place where science and storytelling meet in a very accessible way.
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Adler Planetarium
Sitting right on the lake, the Adler Planetarium offers immersive space-themed exhibits and one of the best skyline views in the city. Its domed theaters create stunning visual journeys through the universe. The historic equipment displays show how astronomy has evolved over the decades.
The outdoor grounds are equally inviting, especially in summer when the lake breeze makes for a perfect photo spot. Nighttime events sometimes let you view the stars above Chicago—a rare treat in a major city.
Chicago Architecture Boat Tour
Chicago’s architectural legacy is best appreciated from the water, where you can see the layers of history in its skyline. Guided tours point out buildings by famous architects and explain the stories behind them. The perspective from the river offers angles you can’t get from the streets.
Whether you’re into design or just enjoy great views, it’s a relaxing yet informative way to explore. Evening cruises often combine city lights with a sense of calm on the water.
Wrigley Field
As one of the oldest ballparks in the country, Wrigley Field carries a sense of nostalgia even for those who aren’t die-hard baseball fans. The ivy-covered outfield walls and hand-operated scoreboard are icons of the sport. Tours of the stadium reveal stories about the Cubs’ long history and the community around the park.
On game days, the atmosphere in the surrounding Wrigleyville neighborhood is electric. Even catching a glimpse from the outside can feel like a piece of Chicago’s culture.
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Magnificent Mile
This stretch of Michigan Avenue packs high-end shopping, historic buildings, and impressive window displays into one busy area. Beyond the retail options, you’ll find landmarks like the Tribune Tower and the Wrigley Building. The blend of architecture and bustling sidewalks gives it a distinctly urban energy.
Street performers and seasonal decorations keep the area lively year-round. It’s a good place to get a sense of the city’s mix of old and new.
Garfield Park Conservatory
Often called ‘landscape art under glass,’ the Garfield Park Conservatory houses thousands of plant species from around the world. Its lush indoor gardens are a welcome escape during Chicago’s colder months. The sprawling glasshouses include desert landscapes, tropical jungles, and seasonal floral displays.
Walking through feels like moving between different climates in minutes. It’s one of the city’s lesser-known gems, making it a peaceful break from more crowded attractions.
Chicago Theatre
With its iconic marquee lighting up State Street, the Chicago Theatre is a piece of living history. The opulent French Baroque-style interior makes even a quick tour feel like stepping back in time. Beyond concerts and comedy shows, the venue hosts film screenings and special events.
The backstage stories add depth to its glamorous public image. Whether you attend a performance or just admire the façade, it’s worth including on your list.
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Deep-Dish Pizza Tasting
Trying Chicago’s signature deep-dish pizza is practically a rite of passage for visitors. These towering pies, with their buttery crusts and layers of cheese and sauce, are a meal in themselves. Popular spots like Lou Malnati’s, Giordano’s, and Pequod’s each have their style and loyal following.
Sharing a pizza here is less about speed and more about savoring the experience. Just be ready for a slower pace—deep dish takes time to bake.
Lakefront Trail
Stretching 18 miles along Lake Michigan, the Lakefront Trail offers paths for walking, biking, and running with constant water views. Different sections provide access to beaches, parks, and public art. The downtown stretch gives dramatic skyline backdrops, while the northern sections feel more residential and laid-back.
Early mornings are especially peaceful before the paths get busy. It’s one of the best ways to see Chicago’s balance of urban and natural scenery.
Museum of Science and Industry
Housed in a historic building from the 1893 World’s Fair, the Museum of Science and Industry is both massive and interactive. Exhibits cover topics from space exploration to transportation, including a full-size replica coal mine. The layout encourages hands-on learning, making it popular with all ages.
Seasonal exhibits and special events add variety to each visit. It’s a place where curiosity gets rewarded with discoveries around every corner.
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A City That Keeps You Coming Back
Chicago’s ability to mix historic landmarks with fresh, evolving attractions means no two trips feel the same. The city’s lakefront setting, cultural diversity, and bold architecture create a blend that’s hard to replicate elsewhere.
First-time visitors often leave with a list of things they didn’t have time to see, already planning a return. Over the decades, Chicago has kept reinventing itself while staying true to its roots.
That balance between old and new is what keeps people coming back.
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