If you’ve never been to Chicago, you’re seriously missing out! This city has everything—breathtaking skyline views, deep-dish pizza that will ruin all other pizzas for you, and some of the best museums in the country. Whether you’re into history, food, music, or just vibing by the lake, Chicago has something for you.
I still remember my first visit to the Willis Tower Skydeck—standing on the glass ledge, heart racing, 1,353 feet above the city. It was terrifying, but also one of the most unforgettable moments of my life. Chicago does that to you—it surprises you in the best way.
So, if you’re planning a trip, here are 15 of the best things to do in Chicago that you absolutely can’t miss!
Walk the Magnificent Mile
Address: Michigan Ave, Chicago, IL 60611
| Type | Shopping, Sightseeing |
| Time to Spend | 1 to 2 hours |
History and Significance: The Magnificent Mile, Chicago’s renowned shopping district, has been a symbol of luxury and elegance since the early 20th century. It has been a central part of the city’s development and a key area for commerce, drawing both tourists and locals.
What to Expect: Expect to see high-end stores, department stores, iconic landmarks like the Wrigley Building, and lively street performances. It’s a place where luxury meets local culture.
Visitor Information: The Magnificent Mile is easily accessible by public transit. Plan to walk, as it stretches for over a mile. The area is open year-round, with special events like parades and street festivals, especially in summer.
If you love shopping, people-watching, or just soaking in the city’s energy, the Magnificent Mile is a must-visit. This iconic stretch of Michigan Avenue is lined with high-end boutiques, department stores, and some of the best restaurants in town. Even if shopping isn’t your thing, the atmosphere here is electric—street performers, luxury brands, and historic landmarks like the Wrigley Building make it an experience worth having. At night, the lights make it even more magical.
Try Chicago’s Famous Deep-Dish Pizza
Address: Chicago, IL, USA
| Type | Food & Drink |
| Time to Spend | 1 to 1.5 hours |
History and Significance: Deep-dish pizza was invented in Chicago in 1943 at Pizzeria Uno, marking the beginning of a deliciously distinct culinary tradition. It’s a symbol of the city’s rich food culture, offering a unique twist on the classic pizza.
What to Expect: Rich, buttery crust, gooey cheese, and savory tomato sauce stacked high make this pizza a meal like no other. Each bite is a layered indulgence of flavors.
Visitor Information: Visit top spots like Lou Malnati’s or Giordano’s. Expect a wait, especially during peak hours, as pizzas take 30-45 minutes to bake. Consider ordering ahead to skip the long lines.
Chicago’s deep-dish pizza is legendary, and you haven’t truly been to Chicago until you’ve taken a bite of this cheesy, sauce-smothered masterpiece. Unlike your regular pizza, deep-dish has a buttery crust, thick layers of cheese, and chunky tomato sauce on top. Lou Malnati’s, Giordano’s, and Pequod’s are the top spots to try this heavenly creation. Pro tip: Order ahead because the baking time takes around 45 minutes!
Take an Architecture River Cruise
Address: 112 E Wacker Dr, Chicago, IL 60601
| Type | Sightseeing, Tour |
| Time to Spend | 1.5 hours |
History and Significance: Chicago is home to some of the world’s most iconic architecture, including the Willis Tower and the John Hancock Center. The architecture river cruise celebrates the city’s architectural history, showcasing its evolution.
What to Expect: On this relaxing boat tour, learn about the architectural styles that define Chicago, with stunning views of modern skyscrapers, historic buildings, and bridges.
Visitor Information: The cruise departs from the riverwalk area, with tickets available on-site or online. It’s a great way to view the city from a different perspective. Evening tours are particularly magical as the city’s lights come alive.
Chicago’s skyline is a masterpiece, and the best way to admire it? A boat ride down the Chicago River! The architecture cruise takes you through the heart of downtown while expert guides tell you fascinating stories about the city’s skyscrapers, including the Willis Tower and Tribune Tower. It’s relaxing, informative, and gives you some of the best photo ops in the city. If you can, book an evening tour when the buildings light up!
Explore Millennium Park & Take a Selfie with The Bean
Address: 201 E Randolph St, Chicago, IL 60602
| Type | Outdoor, Landmark |
| Time to Spend | 1 to 2 hours |
History and Significance: Millennium Park, opened in 2004, is one of Chicago’s most beloved landmarks. It features Cloud Gate, affectionately known as “The Bean,” a symbol of the city’s blend of art and public space.
What to Expect: The park offers iconic sculptures, an outdoor music venue, interactive water features, and space for concerts or ice skating, depending on the season.
Visitor Information: Millennium Park is free to visit year-round. It’s a great stop to relax and people-watch, with nearby cafes and food trucks. Check the schedule for free concerts and seasonal events.
No Chicago trip is complete without a visit to Millennium Park. The star attraction? Cloud Gate (aka The Bean), the giant reflective sculpture that makes for the perfect Instagram shot. But that’s not all! You’ll also find the Jay Pritzker Pavilion, a massive outdoor music venue, and the Crown Fountain, a fun interactive water display. In the summer, the park hosts free concerts, and in the winter, there’s ice skating.
Visit the Art Institute of Chicago
Address: 111 S Michigan Ave, Chicago, IL 60603
| Type | Museum |
| Time to Spend | 2 to 3 hours |
History and Significance: Established in 1879, the Art Institute is one of the oldest and largest art museums in the U.S., housing masterpieces from famous artists like Van Gogh, Monet, and Rembrandt.
What to Expect: Explore over 300,000 works of art, including European and American paintings, contemporary works, sculptures, and decorative arts. The museum’s Beaux-Arts building is as much a work of art as the collections inside.
Visitor Information: The museum is open daily, with special exhibitions and educational programs. It’s located in Grant Park and offers discounted or free entry on certain days or for students.
Even if you’re not an art buff, the Art Institute of Chicago will blow your mind. This world-class museum has over 300,000 pieces of art, including Van Gogh’s The Bedroom, Grant Wood’s American Gothic, and Monet’s Water Lilies. The building itself is stunning, and the museum’s modern wing is a masterpiece. Give yourself time to wander—it’s easy to lose track of time here!
Ride the Ferris Wheel at Navy Pier
Address: 600 E Grand Ave, Chicago, IL 60611
| Type | Amusement, Sightseeing |
| Time to Spend | 1 to 2 hours |
History and Significance: Navy Pier, opened in 1916, is a symbol of Chicago’s waterfront and an iconic recreational space. The Centennial Wheel, built in 2016, offers unparalleled views of Lake Michigan and the Chicago skyline.
What to Expect: Enjoy a scenic ride with breathtaking views from 200 feet up. Besides the Ferris wheel, the pier features shopping, dining, and entertainment options.
Visitor Information: Navy Pier is accessible by public transit, with plenty of parking available. It’s best visited during the summer when fireworks light up the night sky, making for a fantastic evening outing.
Navy Pier is one of Chicago’s top attractions, and the Centennial Wheel is its crown jewel. Standing 200 feet tall, it gives you breathtaking views of Lake Michigan and the Chicago skyline. But there’s more—Navy Pier has great restaurants, street performers, and even boat tours. If you visit in the summer, don’t miss the fireworks show on Wednesday and Saturday nights!
Enjoy a Sunset at 360 Chicago Observation Deck
Address: 875 N Michigan Ave, Chicago, IL 60611
| Type | Observation Deck |
| Time to Spend | 1 to 2 hours |
History and Significance: The 360 Chicago Observation Deck is located in the John Hancock Center, a landmark that’s been part of Chicago’s skyline since 1969. The deck offers some of the best views in the city.
What to Expect: Capture stunning sunset views of Lake Michigan, the city skyline, and four surrounding states. For thrill-seekers, try TILT for a unique angle over the city.
Visitor Information: The deck is open daily, with extended hours for sunset and evening views. Tickets are available online or on-site. It’s a perfect spot for a romantic evening or an exciting experience.
If you want jaw-dropping views of the city, head to the 360 Chicago Observation Deck on the 94th floor of the John Hancock Center. The sunset view from up here is simply magical—Lake Michigan on one side, the skyline on the other. For thrill-seekers, try TILT, a glass platform that tilts you forward over the city!
Experience Live Jazz & Blues
Address: Kingston Mines (2548 N Halsted St) / Green Mill (4802 N Broadway)
| Type | Live Music |
| Time to Spend | 2 to 3 hours |
History and Significance: Chicago is known as the birthplace of blues, with a vibrant music scene dating back to the early 20th century. The city’s jazz and blues legacy continues to thrive in venues like Kingston Mines and Green Mill.
What to Expect: Enjoy live performances by local and touring musicians, showcasing Chicago’s rich music history. The intimate settings make it a memorable experience.
Visitor Information: Check performance schedules online before visiting. These spots offer drinks, light bites, and late-night entertainment. Green Mill has a historic charm, once frequented by Al Capone.
Chicago is the birthplace of the blues, and you can’t leave without catching a live performance. Kingston Mines and Green Mill Cocktail Lounge are the go-to spots for a true Chicago jazz experience. Green Mill, once a hangout for Al Capone, still has its old-school charm.
Walk Along the Chicago Riverwalk
Address: Chicago Riverwalk, Chicago, IL 60601
| Type | Outdoor, Leisure |
| Time to Spend | 1 to 2 hours |
History and Significance: The Chicago Riverwalk is part of the city’s revitalization project, providing a pedestrian-friendly space to enjoy the scenic beauty of the river and the city’s architecture.
What to Expect: Stroll along the water’s edge, enjoying outdoor bars, cafes, and occasional public art. Kayaking and boat rentals are available for those wanting to explore the river more intimately.
Visitor Information: The Riverwalk is free to access and open year-round. It’s a wonderful place to relax, with beautiful views at sunset. During summer, enjoy food festivals and outdoor concerts.
The Chicago Riverwalk is the city’s backyard—a scenic stretch filled with outdoor bars, coffee shops, and stunning skyline views. You can grab a bite at City Winery, rent a kayak, or just take a relaxing stroll. It’s a vibe, especially at sunset!
Check Out the Museum of Science & Industry
Address: 5700 S Lake Shore Dr, Chicago, IL 60637
| Type | Museum |
| Time to Spend | 3 to 4 hours |
History and Significance: The Museum of Science & Industry, established in 1933, is the largest science museum in the Western Hemisphere. It offers a hands-on, interactive experience for visitors of all ages.
What to Expect: Experience fascinating exhibits, including a WWII submarine, a working coal mine, and a tornado simulator. It’s a fantastic museum for kids and adults alike.
Visitor Information: Located in Hyde Park, the museum is open daily, with special exhibits and events throughout the year. Plan 2-3 hours for a full experience.
This place is mind-blowing! The Museum of Science & Industry is home to a real WWII submarine, a giant indoor tornado, and a full-scale replica of a coal mine. It’s interactive, fun, and perfect for all ages.
Take a Food Tour
Address: Various locations across the city
| Type | Food & Drink, Tour |
| Time to Spend | 2 to 3 hours |
History and Significance: Chicago’s food scene is a melting pot of diverse influences, with Italian beef sandwiches, hot dogs, and Chicago-style pizza offering unique local flavors. A food tour introduces visitors to these iconic dishes.
What to Expect: Savor Chicago’s flavors with stops at iconic eateries offering deep-dish pizza, hot dogs, Italian beef sandwiches, and the famous Garrett’s popcorn mix.
Visitor Information: Many food tours are self-guided or led by local experts. Book in advance for group tours or create your own itinerary. Expect to walk and sample multiple dishes during the tour.
Chicago is a food lover’s dream, and trust me, you need to experience it beyond deep-dish pizza. A food tour is the best way to taste the city’s iconic eats in one go. Bite into a juicy Italian beef sandwich, savor the perfect snap of a Chicago-style hot dog (remember—no ketchup!), and grab a bag of Garrett’s famous caramel and cheese popcorn mix. Whether you book a guided tour or create your own, this is a delicious way to explore Chicago’s flavors.
Walk or Bike the Lakefront Trail
Address: Lakefront Trail, Chicago, IL
| Type | Outdoor, Sightseeing |
| Time to Spend | 1 to 2 hours |
History and Significance: The Lakefront Trail is a 18-mile stretch along Lake Michigan, offering spectacular views of both the city and the lake. It’s one of Chicago’s most popular outdoor spaces.
What to Expect: You can walk, jog, or bike along the trail, passing beaches, parks, and stunning skyline views. North Avenue Beach is a great spot for photos.
Visitor Information: The trail is free and open year-round. Bike rentals are available, and there are various entry points along the trail. In summer, it’s a popular spot for fitness enthusiasts.
Chicago has a secret: a stunning, 18-mile trail that runs along the shore of Lake Michigan. Whether you’re walking, jogging, or biking, the Lakefront Trail offers some of the most breathtaking views of the city skyline. On a sunny day, you’ll see locals rollerblading, couples strolling, and bikers cruising past beaches and parks. If you’re looking for a perfect photo spot, stop at North Avenue Beach—it has the best mix of lake and city views!
Visit the Lincoln Park Zoo
Address: 2001 N Clark St, Chicago, IL 60614
| Type | Outdoor, Family-Friendly |
| Time to Spend | 1.5 to 2 hours |
History and Significance: The Lincoln Park Zoo is one of the oldest zoos in the country, founded in 1868. It remains a beloved, free attraction, giving visitors a chance to connect with wildlife.
What to Expect: See animals like lions, tigers, giraffes, and polar bears. During the winter, the zoo hosts ZooLights, a magical light display.
Visitor Information: The zoo is open year-round with no admission fee. It’s a great place for families, with seasonal events and educational programs.
Who doesn’t love free stuff? Lincoln Park Zoo is one of the last free zoos in the U.S., and it’s actually one of the best! You can see lions, penguins, giraffes, and even polar bears—all without spending a dime. The zoo is located in the beautiful Lincoln Park neighborhood, surrounded by gardens and walking paths. It’s the perfect spot for a relaxed afternoon, and if you’re visiting in winter, check out the magical ZooLights festival!
Catch a Game at Wrigley Field
Address: 1060 W Addison St, Chicago, IL 60613
| Type | Sports, Entertainment |
| Time to Spend | 3 to 4 hours |
History and Significance: Wrigley Field, built in 1914, is one of Major League Baseball’s oldest and most iconic stadiums. It’s home to the Chicago Cubs and is steeped in tradition.
What to Expect: Enjoy a game at this historic venue, famous for its ivy-covered walls and classic design. If there’s no game, take a tour to explore the stadium’s history.
Visitor Information: Tours are available year-round, while Cubs games are typically held from April through September. Purchase tickets in advance, especially during peak season.
Even if you’re not a baseball fan, experiencing a Chicago Cubs game at Wrigley Field is something special. This historic stadium, built in 1914, has an old-school charm that makes every game feel like a party. Locals take their Cubs fandom seriously, and the energy is electric—especially if you sit in the bleachers. If there’s no game during your visit, take a stadium tour to explore the press box, dugouts, and ivy-covered walls up close!
Try the Skydeck Ledge at Willis Tower
Address: 233 S Wacker Dr, Chicago, IL 60606
| Type | Observation Deck, Sightseeing |
| Time to Spend | 1 to 1.5 hours |
History and Significance: Willis Tower, formerly known as the Sears Tower, was the tallest building in the world when completed in 1973. Its Skydeck offers one of the best panoramic views of the city.
What to Expect: Step into the Skydeck Ledge, a glass box suspended 1,353 feet above the city. For those not keen on the ledge, the observation deck offers 360-degree views.
Visitor Information: The Skydeck is open daily, with tickets available online for a discount. The Skydeck experience can take up to an hour, especially with crowds.
Do you have a fear of heights? Well, this will test you! The Skydeck Ledge at Willis Tower (formerly the Sears Tower) lets you step into a glass box suspended 1,353 feet above the city. It’s thrilling, a little scary, but totally worth it. The views stretch across four states on a clear day! If you’re not ready for The Ledge, you can still enjoy a 360-degree view of Chicago from the observation deck.
If you’re not ready for The Ledge, you can still enjoy a 360-degree view of Chicago from the observation deck. And if you love exploring iconic cities, don’t miss out on the stunning skyline views in Los Angeles, where you can see the city from Griffith Observatory.
Looking for more thrilling adventures? Denver offers breathtaking mountain-top experiences that will leave you in awe. For those who enjoy a mix of history and charm, Louisville has incredible attractions worth visiting.
If sports and entertainment excite you, Indianapolis has some must-see spots. And for a magical experience, Orlando is the ultimate destination for theme park lovers!