Key Highlights
- Explore iconic Chicago landmarks like Millennium Park to see the famous “Bean” sculpture.
- Take a memorable architecture tour along the scenic Chicago River.
- Enjoy family-friendly fun and incredible city views from the Centennial Wheel at Navy Pier.
- Discover world-class art and science at the city’s renowned museums.
- Indulge in classic Chicago food, including the legendary deep-dish pizzas.
- Relax on the sandy shores of Lake Michigan at one of the city’s beautiful beaches.
Introduction
Welcome to Chicago, Illinois, one of the most beautiful and surprisingly clean cities in America! As the nation’s third-largest city, it masterfully combines rich history with a stunning, modern cultural scene. You might know it as the “Windy City,” but did you know that nickname originally came from politics, not the weather? It was used to describe local leaders as being full of “hot air.” Ready to explore this magnificent city? Let’s get started.
Top Things to Do in Chicago: Attractions and Hidden Gems
Chicago is a city that truly has it all. From the awe-inspiring skyline that defines downtown Chicago to the charming, culture-filled neighborhoods, there is an endless list of attractions to discover. Whether you are a first-time visitor or a returning fan, you will always find something new and exciting to experience.
This guide will walk you through the best things to do in the city. We will cover everything from world-famous landmarks to unique local gems, helping you plan an unforgettable trip.
1. Stroll through Millennium Park and snap a photo with The Bean
A trip to Chicago isn’t complete without a visit to Millennium Park, arguably the city’s most famous urban green space. Located in the Loop, it is the perfect spot to relax, see incredible public art, and enjoy free cultural events and concerts at the Jay Pritzker Pavilion when the weather is nice.
The park’s main attraction is Cloud Gate, affectionately known as “The Bean.” Designed by artist Anish Kapoor, this massive stainless-steel sculpture has a highly reflective surface that creates fascinating distortions of the city skyline. It’s a prime spot for creative photos, but be sure to arrive early if you want to avoid the crowds.
Just a short walk from The Bean, you will find the Crown Fountain. This interactive video sculpture and water feature is another fantastic example of public art. It is especially popular with children during Chicago’s hot summers, providing a fun way to cool off.
2. Take an architecture boat tour on the Chicago River
If you are looking for an amazing activity for a weekend trip, an architecture boat tour on the Chicago River is an absolute must. There is no better way to appreciate the city’s magnificent skyline than from the water. As you glide past massive skyscrapers and historic city blocks, you will gain a unique perspective on Chicago’s architectural marvels.
A guided tour offers more than just pretty views. The guides are often incredibly knowledgeable and passionate, sharing fascinating stories and facts about the buildings and the city’s history. You can choose a daytime cruise or see the city light up on a nighttime tour for a truly magical experience.
Many tours stop at key points along the river, allowing you to capture stunning photos of the skyline from the perfect angle. The Chicago Riverwalk also offers a great place to begin or end your tour, with plenty of riverside cafes and bars to enjoy.
3. Visit the Art Institute of Chicago
For art lovers, the Art Institute of Chicago is an essential stop. As one of the largest museums in the United States, it is a premier cultural institution located in the heart of downtown Chicago. The museum is home to an incredible collection of over 300,000 works of art spanning centuries and continents.
Are you hoping to see some famous paintings? The Art Institute boasts iconic masterpieces such as Edward Hopper’s “Nighthawks,” along with celebrated works by artists like Picasso and Van Gogh. You can easily spend an entire day exploring the diverse exhibits, which feature everything from ancient artifacts to contemporary creations.
Even if you only have a few hours, a visit to the Art Institute is well worth your time. It provides a deep dive into global art history and is considered one of the must-visit museums not just in Chicago, but in the world.
4. Explore Navy Pier and try the Centennial Wheel
Situated on the beautiful shoreline of Lake Michigan, Navy Pier is a bustling waterfront attraction that offers something for everyone. Known as “The People’s Pier,” this lively destination is packed with dining, shopping, and cultural events all year round.
One of the most popular things to do at Navy Pier is to take a ride on the Centennial Wheel. This towering Ferris wheel provides breathtaking, sky-high views of the city and the lake. Interestingly, the original Ferris wheel was invented right here in Chicago, making this ride a nod to the city’s innovative history.
Beyond the wheel, Navy Pier hosts numerous free events, especially in the summer. Some popular attractions include:
- Free fireworks displays every Wednesday and Saturday night between Memorial Day and Labor Day.
- A variety of restaurants and cafes where you can grab a bite with a view.
- Live music, art exhibitions, and a theater for live performances.
5. Discover the Museum of Science and Industry
If you are curious about how the world works, the Museum of Science and Industry is a fantastic destination. Located south of the city center near the University of Chicago, this museum is a great place for hands-on learning and discovery. It is one of the must-visit museums in Illinois for visitors of all ages.
The museum features a wide array of captivating exhibits. You can explore a real German U-505 submarine captured during World War II, walk through a mirror maze, or experience a tornado simulator. Space enthusiasts will be thrilled to see the Apollo 8 command module, the first spacecraft to orbit the moon.
With its focus on interactive displays, the Museum of Science and Industry makes science and history come alive. Whether you are interested in trains, airplanes, or the wonders of space, you will find plenty to keep you engaged for hours. It’s an educational and entertaining outing for the whole family.
6. Walk the Magnificent Mile for shopping and sightseeing
For first-time visitors, a walk down the Magnificent Mile is an essential Chicago experience. This famous stretch of North Michigan Avenue is the city’s premier shopping district, packed with everything from high-end designer boutiques to popular department stores like Bloomingdale’s and Sephora. It’s a shopper’s paradise right in the city center.
But the Magnificent Mile offers more than just retail therapy. The area is also home to some of Chicago’s most recognizable landmarks. Look up to see the iconic Wrigley Building and the impressive 360 CHICAGO observation deck, formerly the John Hancock Center, which offers panoramic views of the skyline.
While you are there, consider visiting the five-story Starbucks Reserve Roastery for a unique coffee experience or stopping by The Drake hotel for traditional afternoon tea. The Magnificent Mile perfectly combines shopping, dining, and sightseeing, making it a vibrant hub of activity.
7. Relax at Oak Street Beach along Lake Michigan
You might not think of beaches when you picture Chicago, but the city has an incredible waterfront along Lake Michigan spanning over 30 kilometers. Oak Street Beach is one of the most popular spots to soak up the sun and enjoy the stunning city views. It feels like an ocean getaway right in the middle of a bustling metropolis.
In the summer, the beach is a hub of activity, with people playing volleyball, swimming, and relaxing on the sand. The Lakefront Trail runs alongside the beach, making it a perfect spot for biking, jogging, or simply taking a leisurely stroll. It is one of the best places for outdoor activities in the city.
What about visiting in the fall? While it might be too chilly for a swim in October, a walk along Oak Street Beach still offers incredible views of the skyline against the autumn sky. The waterfront remains a beautiful place for outdoor recreation, even as the seasons change.
8. Experience live music at a local jazz club
Looking for a unique local experience after a day of sightseeing? Chicago has a deep-rooted history in jazz and blues music, and catching a live show is the perfect way to tap into the city’s soulful side. The live music scene offers incredible live entertainment that truly captures the spirit of Chicago.
Many clubs throughout the city host talented musicians every night of the week. A great option is Andy’s Jazz Club, which offers a fantastic lineup of performers from all jazz genres in a classic, intimate setting. It’s an ideal spot to unwind with a good cocktail and even better music.
Spending an evening in a jazz club is more than just a night out; it is an authentic Chicago experience. Instead of another tourist attraction, this hidden gem allows you to connect with the city’s rich artistic heritage and enjoy a memorable night of world-class performances.
9. Tour the Chicago Theatre and admire its historic marquee
Ask a local about the best attractions, and the Chicago Theatre will surely be on their list. This iconic landmark in the city center is one of the most photographed spots in Chicago, thanks to its dazzling, six-story-high marquee. Even if you just walk by, snapping a picture of the glittering “CHICAGO” sign is a must.
Built in 1921, the theatre is just as stunning on the inside. Its French Baroque-style interior features grand staircases, beautiful murals, and a magnificent crystal chandelier. To see it for yourself, you can book a guided tour that takes you behind the scenes of this historic venue.
Of course, the best way to experience the theatre is by seeing a show. Today, it hosts a wide range of live entertainment, from concerts by music legends to comedy shows and Broadway productions. It’s a premier venue that continues to be a cornerstone of Chicago’s cultural scene.
10. Taste famous Chicago deep-dish pizza at a local eatery
When it comes to great food in the United States, Chicago’s deep-dish pizza is in a league of its own. This iconic dish, with its thick crust, inverted layers of cheese and toppings, and hearty tomato sauce, is a must-try for any visitor. Forget what you know about traditional pizza; this is a true culinary experience.
Where should you go for this famous local eat? The city is home to a fierce rivalry between two pizza giants: Lou Malnati’s and Giordano’s. Locals are passionately divided on which one is the best, so you really can’t go wrong with either. The only way to know for sure is to try them for yourself!
Whether you are a pizza purist or an adventurous foodie, indulging in one of these famous deep-dish pizzas is essential. It’s a delicious and satisfying way to taste a piece of Chicago’s culinary history.
11. Wander through Lincoln Park and visit the free Lincoln Park Zoo
If you are looking for family-friendly things to do, Lincoln Park is the perfect destination. As the largest park in Chicago, this sprawling green space along Lake Michigan offers endless opportunities for outdoor activities. You will find sports fields, beautiful gardens, walking paths, and peaceful lakes.
A major highlight of the park is the Lincoln Park Zoo. Established in 1868, it is one of the oldest zoos in North America and, best of all, it’s completely free to enter! The zoo is home to a diverse range of animals and is well-maintained, making it a wonderful place for families to spend an afternoon.
Beyond the zoo, Lincoln Park itself is a great escape from the urban hustle. It is a popular spot for locals to exercise, picnic, or simply enjoy a sunny day. With so much to see and do, it’s an ideal spot for a relaxing and fun-filled family outing in Chicago.
12. Marvel at Buckingham Fountain in Grant Park
Located in the heart of Grant Park, Buckingham Fountain is one of Chicago’s most treasured landmarks and a must-see attraction for first-time visitors. As one of the largest fountains in the world, its scale is truly impressive. The fountain’s design is inspired by the Latona Fountain at the Palace of Versailles.
From mid-April to mid-October, the fountain comes to life with spectacular water shows, shooting water over 40 meters into the air. After dusk, the display is enhanced with a dazzling light and music show that runs every hour, creating a magical atmosphere in the city center.
Does the fountain look familiar? If you are a fan of 90s TV, you might recognize it from the opening credits of “Married with Children.” Its grandeur and beauty make it a fantastic spot for photos and a perfect place to relax while exploring Grant Park.
13. Explore street art in Wicker Park and Logan Square
For a taste of Chicago’s creative and trendy side, head to the neighborhoods of Wicker Park and Logan Square. These areas are known for their vibrant street art scene, with colorful murals and graffiti art adorning buildings and walls. It’s like an open-air art gallery that offers a different kind of sightseeing experience.
Wicker Park is often described as one of Chicago’s “hipster” neighborhoods, full of cool bars, independent boutiques, and a laid-back vibe. Milwaukee Avenue is the main thoroughfare, offering a more eclectic shopping experience compared to the Magnificent Mile. You will find vintage shops alongside trendy indie brands.
Exploring these neighborhoods is a great way to see the real, everyday life of the city. Forget the downtown crowds and instead wander through these artistic communities to discover some of Chicago’s most dynamic and evolving cultural landscapes.
14. Discover hidden gems in Pilsen, including Mexican food and murals
If you are hunting for unique local experiences and hidden gems, the neighborhood of Pilsen is a must-visit. This vibrant area has a large and historic Mexican community, and its culture is proudly displayed through colorful street murals and, of course, incredible food.
A visit to Pilsen offers a rich cultural immersion. The streets are a canvas for stunning murals that tell stories of Mexican heritage and social history. After exploring the art, you can treat yourself to some of the most authentic Mexican food in Chicago. There are countless taquerias and restaurants to choose from.
Here are a few things you shouldn’t miss in Pilsen:
- Visit the National Museum of Mexican Art, which is free to enter and showcases beautiful artwork.
- Grab a delicious meal at a highly-rated spot like 5 Rabanitos Restaurante & Taqueria.
- Simply wander the streets to admire the vibrant murals.
15. Bike or walk the 606/Bloomingdale Trail
For a fantastic outdoor activity, check out The 606, also known as the Bloomingdale Trail. This innovative park is a converted, disused elevated railway line that now serves as a scenic trail for walking, jogging, and biking. Spanning nearly three miles, it connects several neighborhoods, including Logan Square and Wicker Park.
Walking or biking along The 606 gives you a unique perspective of the city, as you travel above the rooftops and streets. The trail is lined with green spaces, public art installations, and benches where you can stop and take in the views. It’s a favorite spot for locals to get some exercise and fresh air.
This is a great option for outdoor fun year-round. Even in October, the trail is a beautiful place for a brisk walk or bike ride, with the changing leaves providing a lovely backdrop. It’s a refreshing break from the typical city sightseeing experience.
Conclusion
Chicago is a city brimming with excitement, culture, and vibrant experiences. From the iconic Millennium Park to the bustling streets filled with hidden gems, there’s no shortage of activities to fill your itinerary. Whether you’re wandering through world-class museums, savoring the deep-dish pizza, or soaking in live jazz music, each moment spent in Chicago will create lasting memories. So, pack your bags and get ready to explore all that this magnificent city has to offer! And if you’re looking for personalized recommendations or need assistance planning your trip, don’t hesitate to reach out and get a free consultation with our travel experts!
Frequently Asked Questions
What are the must-see attractions for first-time visitors in Chicago?
First-time visitors to Chicago should prioritize must-see attractions in the city center. Start with Millennium Park to see “The Bean,” take an architecture boat tour to admire the skyline, and explore the shops and landmarks along the Magnificent Mile in downtown Chicago for a perfect introduction.
Which Chicago neighborhoods are best for sightseeing and activities?
Different Chicago neighborhoods offer unique experiences. Lincoln Park is great for its free zoo and green spaces. Head to Wicker Park for trendy shops and vibrant street art. For an incredible dining scene, the West Loop is one of the best neighborhoods for food lovers to explore.
Where should I go in Chicago for great food or local eats?
For classic local eats in Chicago, you must try the famous deep-dish pizzas from rivals like Lou Malnati’s or Giordano’s. If you are craving authentic Mexican food, the Pilsen neighborhood is filled with amazing restaurants. The city is a food paradise with endless options to discover.