This Midwest Metropolis Is Home to Iconic Skyscrapers, Deep-Dish Pizza, and Stunning Lakefront Views

The top things to do in Chicago, such as shopping at the Navy Pier and museum hopping in the Loop, offer endless fun for visitors of all ages. No matter when you visit, this world-class city delivers plenty of fun. 

As the third largest city in the US, Chicago draws in over 50 million tourists annually. Discover masterpieces at The Art Institute of Chicago, cheer on the Cubs at historic Wrigley Field, or stroll through the Lincoln Park Zoo. And, of course, try a slice of deep-dish pizza or a classic Chicago-style hot dog. 

To create this list, we analyzed traveler reviews, Google ratings, and expert recommendations to highlight the most popular attractions in Chicago. These destinations represent the best of the city—beloved by locals and highly rated by travelers. From iconic landmarks to hidden gems, this guide will help you plan your visit.

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In a Nutshell

Top Hotels

• Luxury: The Langham Chicago
• Mid-range: SpringHill Suites by Marriott Chicago Chinatown
• Budget: The GEM Museum Suites

Top Experiences

• See a game at Wrigley Field
• Visit the Lincoln Park Zoo
• Sail on Lake Michigan

See a Game at Wrigley Field

Wrigley Field is the second oldest baseball stadium in the US. It was built in 1914 as the home of the Chicago Cubs. It has since become a national treasure and a must-see icon of sports history. 

Visit to see a Chicago Cubs game live. This incredible experience brings you into the iconic stadium where you’ll cheer for the Cubs or at least pretend to. Order Chicago-style hot dogs and yell at the top of your lungs for your team. 

If there’s no game, visit the stadium on a guided tour. You’ll learn about its long history and see backstage memorabilia. You’ll also learn about its role in sports history and the history of the city. 

Travel Tips

• Check Out Gallagher Way: This area next to Wrigley Field often hosts events, food vendors, and activities.

Read also: Weekend Getaways in the US

Go Sailing on Lake Michigan

Sailing on Lake Michigan is one of the best things to do in the city. There are over ten harbors, each with a distinct vibe and range of activities. 

The best place to try sailing the high seas, or high lake really, is Chicago Sailboat Charters. You can book a private or group cruise and sail into the sunset. 

Look back and see the Chicago skyline and its famous skyscrapers. Visit offshore monuments such as the William E. Dever Crib Lighthouse. And finish with a sunset over the city. 

Travel Tips

• Stay Close to the Shore: If you’re new to sailing, stay closer to the shore.
• Check the Weather: Be aware of potential storms or high winds that could make sailing dangerous.

Read also: US Islands With Stunning Beaches

See Natural History at the Field Museum

The Field Museum is one of the country’s most visited and beloved natural history museums. You’ll come face to face with dinosaur skeletons and interactive exhibits that take you through the planet’s history. 

Visit throughout the week, but show up early to beat the crowds. Time your visit with majestic experiences and events. 

Don’t miss seeing Sue, the largest and most complete T-Rex skeleton. You’ll also see thousands of years of human history through artifacts and photos. Set aside an entire morning or day because this museum will leave you in awe. 

Travel Tips

• Check for Special Events: Before your visit, check the museum’s website for special events or temporary exhibits. 
• Plan for a Full Day: This will give you enough time to see exhibits like Sue the T-Rex and the Ancient Egypt exhibit.

Read also: Top US Lake Destinations

Sample the City’s Cuisine

Chicago’s food scene is one of the most renowned in the US. The city has 19 Michilin-starred restaurants. Smyth and Alinea have three Michelin stars and are some of the US’ most praised fine dining establishments. 

Besides its world-renowned gourmet cuisine is its street food. Try Chicgo-style hotdogs and deep-dish pizza. You’ll also have some of the country’s best Chinese, Mexican, and Middle Eastern cuisine. 

Take a food tour with Chicago Food and City Tours. This original tour takes you deep into the city’s culinary heart, where you’ll sample endless cuisine unique to The Windy City. Show up hungry, or you’ll have trouble keeping up!

Travel Tips

• Explore Food Markets: Visit local food markets like the Chicago French Market or Maxwell Street Market.
• Try a Food Tour: Join a food tour of Chicago’s iconic dishes, deep-dish pizza or Italian beef sandwiches.

Read also: Stunning Coastal Cities in the US

See Fine Art at The Art Institute of Chicago

The Art Institute of Chicago is one of the world’s most celebrated art museums. You’ll see over 300,000 pieces of fine art that span centuries. Visit early to beat the crowds and enjoy the expansive collections at your leisure. 

You’ll see world-famous paintings such as Georges Seurat’s A Sunday on La Grande Jatte. Pop-culture icons such as Under the Wave off Kanagawa by Katsushika Hokusai are also on display. There are also timeless artifacts from ancient history as well. 

Take a tour of the museum to get in-depth knowledge of each priceless piece. There are also tours, special art events, and lectures by visiting and local artists. No matter when you visit, you’ll have non-stop fun. 

Travel Tips

• Explore the Thorne Miniature Rooms: These intricate miniature displays show different historical periods in detail.
• Use the Museum App for Audio Guides: You will learn more about each piece at your own pace.

Read also: Relaxing Harbor Towns in the US

Spend the Evening on Navy Pier

Navy Pier is a former Naval Pier and home to countless rides, museums, and shops. Visit with your family or alone and enjoy the fun vibes and sights. 

The Navy Pier offers plenty of carnival rides, including the Centennial Wheel. You’ll get to enjoy games and monthly events. After enjoying the rides, hop into boutique shops and grab a bite to eat at a restaurant looking over the water. 

The pier has tons of boats and tours to experience as well. See the Tall Ship Windy and even sign up for an excursion. You’ll join several others on this massive sailing vessel before returning to the pier. 

Travel Tips

• Explore the Dining Options: Try deep-dish pizza at the highly rated Giordano’s.
• Wear Comfortable Shoes: You will do a lot of walking exploring the Navy Pier.

Read also: Must-Visit Cities in the US

Visit the Willis Tower

The Willis Tower was the tallest building in the world from 1974 to 1998. It rises 1,450 feet (443m) and 110 stories. You can see the state of Michigan across the lake from the top. 

When you visit, head up to the observation deck at the top of the tower. Walk out on the Skydeck and look down at the city. You’ll have a bird’s eye view of the city’s other famous monuments and skyscrapers. 

After seeing the view, grab a bite in the tower’s dining court. Then, head out on the terrace to enjoy fresh air and beautiful gardens. 

Travel Tips

• Bring a Polarizing Filter for Your Camera Lens: This reduces glare on the glass. 
• Check for Sunset Times: Arrive 30-45 minutes before sunset to get a good spot.

Read also: Insta-Worthy Spots in the US

Experience Chicago’s Theaters

If you’re a theater fan, there’s nothing like experiencing Chicago’s theaters. These historical venues are worth exploring for a week. 

Start at the historic Civic Opera House, also known as the Lyric Opera House. This timeless building is one of the largest opera houses in the US. It was founded in 1954 and has seen some of the greatest entertainers in American history. 

Another must-see theater is the iconic Chicago Theatre. This theater was built in 1921 and has become one of the country’s most iconic performance spaces. Check out live music, plays, and famous productions in this timeless venue. 

Travel Tips

• Book a Behind-the-Scenes Tour: The Civic Opera House and Chicago Theatre offer backstage tours. Tickets are about $15–$20.
• Arrive Early for Best Photos: If you want great pictures, especially of the Chicago Theatre marquee, get there early in the morning.
• Grab Dinner Nearby: Try Petterino’s near the Civic Opera House. Their classic American menu and theater-themed décor make it perfect for a night out—book in advance.

Read also: US Destination for Art Lovers

Visit the Lincoln Park Zoo

The Lincoln Park Zoo features endless family entertainment and rare animals. The zoo is an important space for animal conservation and education. No matter how old you are, you’re bound to learn and have much fun. 

The zoo was founded in 1868, making it one of the US’ oldest zoos. You’ll see animals like lions, giraffes, monkeys, and penguins. 

Visit during the holidays for special events. In winter, the zoo becomes one of the best holiday light displays in the country. Check the website and time your visit with special events and performances for an unforgettable experience. 

Travel Tips

• Download the Zoo’s App: The app has an interactive map and animal feedings.

Read also: Most Beautiful US Cities

Listen to Live Music

Chicago’s music scene is diverse and influential. From jazz to hip-hop, the city is home to iconic artists that have changed music forever. Artists such as Sam Cooke, The Smashing Pumpkins, and Earth, Wind & Fire have gone on to international stardom. 

Head to the city’s live music venues such as The Hideout and The Jazz Showcase to see up-and-coming artists. You’ll dive deep into the city’s musical heritage and come face to face with rising talent. 

Besides the iconic live music venues, check out the city’s small bars and clubs. There are endless destinations where the city’s top performers play their heart’s out for the crowd. 

Travel Tips

• Check Out Open Mic Nights: Many bars and clubs in Chicago have open mic nights, where you can see up-and-coming artists.

Read also: US Cities With Interesting Nightlife

Shop Along the Magnificent Mile

The Magnificent Mile stretches along Michigan Avenue. Some of the country’s most iconic stores and boutique shops are along the historical street. 

Buy memorabilia at stores such as the Chicago Cubs Team Store. Then, see the Historic Water Tower, one of the city’s most iconic monuments. 

You’ll look up at iconic buildings such as the Tribune Tower and other monuments built at the turn of the century. Visit 875 North Michigan Avenue for one of the best views of the city. The entire city, including the massive Willis Towe, is standing nearby. 

Travel Tips

• Take Advantage of Tax-Free Shopping: Illinois does not charge sales tax on clothing and shoes. 
• Use Public Transportation: Buses and trains make it easy to explore.

Read also: Incredible Wilderness Areas in the US

Explore Chicago’s Art Scene

Chicago’s art scene is thriving, historical, and influential. Start by seeing the iconic Cloud Gate sculpture in Millennium Park. Also known as ‘The Bean,’ this statue is a must for photos. 

Visit museums such as the National Museum of Mexican Art. This thriving institute features almost 20,000 pieces from some of the US and Mexico’s top artists. 

Then, explore the city’s famous art galleries to see and buy fine art. There are dozens of galleries to choose from including small private exhibits to large industrial warehouses. 

Travel Tips

• Join Gallery Walks: Many neighborhoods, such as the Chicago Arts District in Pilsen, have monthly gallery walks.
• Explore Street Art: Chicago has a lively street art scene, especially in neighborhoods like Pilsen and Wicker Park.

Read also: Relaxing US Mountain Getaways

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