As Amazon Associates, we may receive a commission for purchases made through our affiliate links.
Chicago is one of the most exciting cities in the world.
It boasts an absolutely iconic skyline, a deep and fascinating history, and a culture that is vibrant and welcoming.
Plus, if you love food, you already know Chicago is world-class, whether you’re craving deep-dish pizza or a fancy dinner.
For travelers, Chicago truly has something for everyone.
It is a must-visit city that offers stunning architecture, amazing museums, and friendly, bustling neighborhoods.
I promise you will never run out of things to see or do here.
It is simply a place that you have to experience to fully understand.
From the famous downtown sights to the hidden local favorites, your trip starts now.
Here are 20 of the best things to do in Chicago, from classic attractions to local gems.
1. See Your Reflection at The Bean
You simply cannot visit Chicago without taking a picture at Millennium Park, and the Cloud Gate sculpture, known to everyone as The Bean.
I remember walking up to it for the first time; it is much bigger and more stunning in person than in pictures.
The way the stainless steel surface perfectly reflects the amazing Chicago skyline and the park around you is truly breathtaking.
It’s a fun, free, and beautiful way to start your day downtown, capturing a perfect memory of the city.
2. The City from The Ledge at Willis Tower
If you want the absolute best view of the entire city, you must head up the Willis Tower Skydeck.
I remember being up there and feeling like I could see forever, tracing the shore of Lake Michigan and picking out all the famous landmarks from above.
But the real thrill is stepping out onto The Ledge.
It’s a glass box that extends four feet out from the building, and standing on that clear floor 103 stories up will truly give you a rush.
It’s a classic Chicago experience you can’t miss.
3. Ride the Centennial Wheel at Navy Pier
Navy Pier is a huge, fun playground right on the edge of Lake Michigan, and it’s a great spot to spend an afternoon.
The main event for me was riding the giant Centennial Wheel.
When you’re up at the top, you get these fantastic, sweeping views of the water, the beaches, and the entire city skyline.
It’s truly stunning!
Plus, there are always cool events, gardens to walk through, and plenty of places to grab a bite to eat.
It is a classic, joyful Chicago spot.
4. Stroll on the Chicago Riverwalk
The Chicago Riverwalk is easily one of the best places in the city to just relax and take in the amazing architecture.
I love walking along the water here; it feels calm, even though you’re right in the middle of downtown.
You can watch the boats pass and look straight up at the towering buildings that line the river, getting a completely different view than you would from the street.
It’s also the perfect place to grab a coffee or a drink at one of the little cafes and just enjoy being part of the city’s energy.
5. Visit The Art Institute of Chicago
The Art Institute of Chicago is not just a museum, it is a world-class experience, and you could spend days here without seeing everything.
I remember being completely mesmerized by the famous Impressionist and Post-Impressionist collections.
Seeing works by Monet and Van Gogh up close is always unforgettable.
The sheer variety, from ancient artifacts to modern photography, means there is always something incredible to discover around every corner.
It’s a peaceful, inspiring place that you absolutely must dedicate a few hours to exploring.
6. Explore Griffin Museum of Science and Industry
If you love hands-on learning and seeing amazing feats of engineering, you absolutely must visit the Griffin Museum of Science and Industry.
I always set aside a full day for this place because the exhibits are truly massive and engaging.
Where else can you climb inside a real captured German U-boat or walk through a massive, two-story recreation of a tornado?
I still remember the excitement of plunging down into the replica coal mine.
It is a fantastic, interactive museum that makes complex science feel fun and thrilling for everyone, no matter your age.
7. Come Face-to-Face with Sue at the Field Museum
The Field Museum is an absolute treasure, and the star attraction is, without a doubt, Sue, the T. rex.
I remember walking into the main hall and being completely stunned by the sheer size of her skeleton.
It’s the largest and most complete T. rex ever found.
Beyond the dinosaurs, the museum holds incredible collections on everything from Ancient Egypt to diverse world cultures.
It is a fantastic place to spend hours exploring natural history, learning about the planet, and feeling like a true explorer.
8. Explore Shedd Aquarium
The Shedd Aquarium offers one of the best experiences to connect with marine life, even in the middle of a big city.
When you walk through the various exhibits, you are immediately transported to different oceans and aquatic habitats.
I loved watching the playful beluga whales and the energetic sea otters.
The huge Abbott Oceanarium is fantastic, making you feel like you are right on the Pacific coast.
It is a peaceful, beautiful place where you can relax and truly appreciate the incredible diversity of life underwater.
9. Cosmic Planetarium Journey
The Adler Planetarium is a stunning place located right on the Museum Campus, offering incredible views of Lake Michigan even before you go inside.
I found the shows in their dome theaters to be absolutely mesmerizing.
They truly make you feel like you are soaring through space and discovering new galaxies.
It is a wonderful way to connect with the universe and learn about stars, planets, and astronomy in a fun, engaging way.
You leave feeling small, yet totally inspired by the vastness of the cosmos.
10. See a Game at Wrigley Field
Visiting Wrigley Field is like stepping back into baseball history.
It is a truly special place, whether you love the Cubs or not.
I remember sitting in the stands, looking out at the famous ivy-covered outfield walls, and feeling the energy of the crowd, it is absolutely electric.
The atmosphere is historic and totally different from modern stadiums.
Going to a game here is not just about baseball.
It is about experiencing a deeply beloved piece of Chicago tradition and soaking up the passionate local spirit.
11. Meet Animals at Lincoln Park Zoo
I always suggest the Lincoln Park Zoo because it is one of the very best free zoos in the country, and it is set in such a gorgeous park.
I love that you can wander through and see everything from gorillas to polar bears without spending a dime.
It is a fantastic place to spend a relaxed morning or afternoon, enjoying the beautiful landscaping and watching the animals.
Plus, being located right on the lake makes the whole experience feel like a peaceful getaway inside the city.
12. Window Shop the Magnificent Mile
The Magnificent Mile is simply the place to be if you enjoy world-class shopping, dining, and seeing incredible landmarks.
I love walking along this section of Michigan Avenue, surrounded by beautiful architecture and famous storefronts.
It’s an energetic, upscale area perfect for window shopping or finding something truly special.
You’ll see historic buildings next to modern skyscrapers, making it a wonderful stroll that perfectly captures the busy, stylish heart of Chicago.
13. Admire Grant Park and Buckingham Fountain
Grant Park is known as Chicago’s front yard, and the centerpiece is the breathtaking Buckingham Fountain.
I remember visiting at night when they light it up, it is truly spectacular, with water displays reaching high into the air.
It’s a huge, beautiful green space perfect for an afternoon picnic or a scenic walk with stunning views of the skyline surrounding you.
The fountain is an amazing sight, especially when the water dances with the colored lights in the evening.
14. Garfield Park Conservatory
The Garfield Park Conservatory is one of my absolute favorite peaceful spots in the city.
It’s like stepping into a tropical oasis, no matter what the weather is outside.
I love wandering through the huge, glass-enclosed rooms filled with exotic palms, desert plants, and lush greenery.
It’s incredibly calming and beautiful.
If you need a moment of quiet reflection away from the city noise, this massive, stunning greenhouse is the perfect place to find warmth and natural beauty.
15. Bike or Walk the Lakefront Trail
The Lakefront Trail is a massive, miles-long path right along the shore of Lake Michigan, and it’s fantastic for exercise or just a scenic walk.
I always rent a bike when I visit and spend a couple of hours riding with the water on one side and the stunning city skyline on the other.
It’s a huge resource for running, biking, or simply enjoying the fresh air and sunshine.
It makes the city feel open and connected to nature.
16. Look Up at the Chicago Cultural Center
The Chicago Cultural Center is a true hidden architectural gem, and the best part is that it is absolutely free to enter!
I remember walking inside and immediately looking up, completely stunned by the two massive, gorgeous stained-glass domes, especially the huge Tiffany dome.
It’s a breathtaking display of beautiful craftsmanship and history.
The center also hosts free concerts, exhibits, and events, making it a perfect, peaceful stop to soak up some of Chicago’s artistic elegance.
17. The View from 360 Chicago
If you want a truly unique thrill with your city view, you have to go to the 360 Chicago Observation Deck, located in the former John Hancock Center.
The view from the 94th floor is absolutely incredible, giving you sweeping panoramas of the city and Lake Michigan.
But for the brave, the TILT experience is a must-try.
I remember holding onto the railings as the glass platform tilted outward over Michigan Avenue.
It is a fantastic, heart-pounding way to experience Chicago from above!
18. Tour the Historic Chicago Theatre
The Chicago Theatre is much more than just a venue.
It is an incredible piece of city history and dazzling architecture.
I loved taking the tour and hearing all the stories about the famous performers who have graced that stage.
Walking into the main hall and seeing the stunning vaulted ceilings, the famous marquee, and the gorgeous details makes you feel like you have stepped back into the golden age of entertainment.
It is a truly glamorous and unforgettable Chicago landmark.
19. Chicago History Museum
If you want to understand why Chicago is the unique and amazing city it is today, the Chicago History Museum is the place to go.
I found the exhibits so engaging, telling the story of everything from the Great Fire to the city’s role in jazz music.
It is packed with fascinating artifacts and personal stories that really bring the past to life.
Spending time here gives you a much deeper appreciation for the resilience and spirit of the people who built this incredible place.
20. Lincoln Park Conservatory
The Lincoln Park Conservatory is a hidden gem that offers a beautiful, warm escape, perfect for any time of the year.
I love visiting these gorgeous Victorian glass houses, especially in the winter when the air outside is cold.
Walking among the stunning palm trees, ferns, and seasonal flower displays is incredibly peaceful and refreshing.
It’s a wonderful, free place to enjoy incredible horticultural beauty and take some truly amazing photos.
Conclusion
Chicago truly is a city that delivers on every front.
From towering skyscrapers and rich history to world-class art, amazing food, and fun on the lake, it offers a complete, vibrant travel experience.
I hope this list encourages you to move beyond just the famous sights.
To truly enjoy the city, make sure you mix those iconic downtown stops like The Bean and the Skydeck with the fantastic local neighborhood experiences like the parks and museums further afield.
This blend is what makes a Chicago trip so memorable and unique.
Start planning your adventure today!