Known around the world as the Windy City, Chicago is a Midwestern gem that can’t be missed.
As one of the US’s most important cities, there’s certainly a wide variety of things to do and if you’re only visiting the city for a few days, it can be difficult to know where to go.
That is why I wanted to show you the absolute best things to do in Chicago that won’t leave you disappointed.
Insider Tip: To save money, you should consider purchasing a Chicago CityPASS which gives you free access to the city’s top attractions.
Table of Contents
1. Visit Millennium Park and see the iconic Cloud Gate sculpture (the Bean)
Millennium Park, located in the heart of Chicago, is a vibrant 24.5-acre urban park surrounded by skyscrapers that features lush gardens and public artwork.
Among its most iconic features is the Cloud Gate sculpture, commonly known as “The Bean” which has become a symbol of Chicago.
Designed by British artist Anish Kapoor, this massive, stainless steel structure reflects the city’s skyline and the surrounding park with its mirror-like surface.
Don’t forget to take a selfie in the reflection!
2. Visit 360 Chicago
Located on the 94th floor of the John Hancock Center, this observation deck offers a 360-degree panorama of the city.
You can see famous landmarks like Navy Pier, Millennium Park and Lake Michigan from here.
One of the main highlights is TILT, a thrilling glass enclosure that tilts outward giving you downward views of the city from 1,030ft. There’s nothing quite like it.
They also have the CloudBar which is basically a bar in the sky! It’s the perfect place to enjoy a tasty cocktail or refreshing drink.
Warning: 360 Chicago often reaches capacity at peak times so I’d recommend pre-booking your ticket online to avoid disappointment.
3. Count the building fragments embedded in the Tribune Tower
Located on the Magnificent Mile, you’ll find around 150 fragments from famous buildings around the world, embedded into the base of the Tribune Tower.
As you explore the exterior, you’ll spot pieces from the Great Wall of China, Pompeii, the Taj Mahal and even chunks of the Berlin Wall.
Every fragment is labeled so you know exactly where it came from. Most of them were embedded into the tower walls in the 1920s when the tower was originally built.
However, newer fragments are added from time to time. The most recent one was a piece of steel from the World Trade Center in New York that was sadly destroyed in 2001.
4. Take an architectural boat tour to learn about the city’s stunning buildings
I’d highly recommend joining this Chicago River Architecture Tour. You’ll spend an hour cruising through Lake Michigan, admiring Chicago’s impressive skyline.
You’ll be wowed by unparalleled views of Chicago’s most famous buildings like the Willis Tower, the Wrigley Building and the neo-Gothic Tribune Tower.
Even better, you’ll be joined by an expert who will give you all the details on the history. It’s absolutely fascinating!
This tour is super popular and often sells out so I’d recommend booking your ticket ahead of time so you don’t miss out.
5. Stroll along Navy Pier & ride the ferris wheel
Chicago’s Navy Pier, which extends into Lake Michigan, is a bustling hub of entertainment that’s not to be missed.
One of its most famous attractions is the 200-ft Centennial Wheel, a large Ferris wheel offering breathtaking views of the city skyline and Lake Michigan itself.
I’d highly recommend riding the ferris wheel (if you’re not too scared of heights), especially at night, as the views are truly breathtaking.
Alongside the Ferris wheel, Navy Pier also features a variety of attractions including parks, theaters, museums and a wide range of dining options.
Insider Tip: Offshore Rooftop is my favorite restaurant on Navy Pier. It actually features the largest rooftop deck in the entire US!
6. Get a Bird’s-Eye View of Chicago From Skydeck Chicago
Located on the 103rd floor of the iconic Willis Tower (Chicago’s tallest building), the Skydeck is one of the tallest observation decks in the world.
Tourists can step onto “The Ledge” which is a series of glass-floored balconies that extend out from the building.
The panoramic views of Chicago’s skyline, Lake Michigan and beyond are truly breathtaking.
In fact, on a clear day, you can actually see 4 different states from up here.
You can pre-book your Skydeck Chicago admission ticket here. I’d recommend doing this if you want to visit as this place often reaches capacity!
7. Enjoy a scenic walk or bike ride along Lake Michigan’s shoreline
The Lakefront Trail is an 18-mile long path that winds along Lake Michigan’s western shore, providing stunning views of both the water and the Chicago skyline.
Whether you’re leisurely strolling, jogging or cycling, this scenic route takes you past beaches, grassy parks and recreational areas.
8. Attend a comedy show at The Second City
This iconic comedy club, located in the Old Town neighborhood, has a long history of launching the careers of famous comedians, including Tina Fey, Stephen Colbert and Steve Carell.
Visitors can enjoy improvisational comedy performances that are witty, sharp and often politically satirical.
The intimate atmosphere and talented cast create a night full of laughter, making it a great choice for a fun evening out.
9. Visit the Adler Planetarium
Located right by Lake Michigan, this is America’s first ever planetarium and has lots of exciting things to see and do.
You can watch amazing shows in the dome theater that takes you on a journey through the universe, and explore exhibits about planets, stars and space exploration.
It’s really cool for both kids and adults because you can learn a lot about astronomy and even get a chance to look through telescopes.
10. Explore the Art Institute of Chicago
The Art Institute of Chicago is one of the world’s leading art museums, renowned for its extensive collection that spans literally thousands of years.
Remarkably, their collection covers all cultures and all historical periods!
It houses nearly 300,000 works of art, including several masterpieces by the likes of Van Gogh, Picasso and Warhol.
It’s also one of the oldest and largest art museums in the whole of the US!
I’d recommend pre-booking a skip-the-line ticket to save time (the queues are notoriously long here so this allows you to bypass the queues entirely!).
11. Take a stroll along the colorful Chicago Riverwalk
The Chicago Riverwalk is a 1.25-mile pathway that runs right next to the Chicago River, offering beautiful views and a peaceful place to walk.
As you go, you’ll see a mix of modern skyscrapers and older buildings, showing off Chicago’s impressive architectural history.
There are also plenty of spots to sit and relax, grab a bite to eat or just watch the boats go by.
12. Try deep-dish pizza
Trying deep-dish pizza in Chicago is a must-do experience for any food lover.
This type of pizza is unique because of its thick, buttery crust that’s baked in a deep pan.
It’s like a pie filled with layers of cheese, toppings and a rich tomato sauce on top.
What makes it special is the upside-down order of ingredients compared to traditional pizzas, with cheese directly on the crust, followed by toppings and then the sauce.
Insider Tip: One of the best places to try authentic deep-dish pizza in Chicago is at Giordano’s!
I’d highly recommend joining this Chicago Walking Food Tour if you want to try all of Chicago’s most famous dishes including deep-dish pizza, hot dogs and more.
You’ll also get the chance to visit some of Chicago’s most famous landmarks including Millenium Park and learn about the city’s history!
- Chicago Food Walking Tour (highly rated)
13. Shop on the Magnificent Mile, Chicago’s famous shopping district
This famous stretch of Michigan Avenue is lined with a wide range of stores, from high-end designer boutiques to popular retail chains, offering something for every shopper.
The Magnificent Mile isn’t just about buying things – it’s an experience in itself.
You can enjoy window shopping, explore flagship stores and even take breaks at cozy cafes and restaurants.
This shopping paradise is a must-visit for those looking to indulge in some of the best shopping Chicago has to offer.
14. Catch a Broadway show at the Nederlander Theatre
The Nederlander Theatre is an iconic and historic venue known for its lavish interiors. It was originally opened in 1926 as the Oriental Theatre but was renamed in 2019.
The Nederlander Theatre hosts a variety of Broadway shows, ranging from classic musicals to contemporary productions, showcasing some of the finest talents in the theater world.
As the curtain rises and the lights dim, audiences are transported into captivating stories and mesmerizing performances.
15. Have a picnic in Grant Park
This large, beautiful park, often called “Chicago’s front yard,” stretches along the Lake Michigan shoreline and offers stunning views of the city skyline.
It’s filled with open green spaces, lovely gardens and winding paths perfect for walking or biking.
In Grant Park, you’ll find many famous attractions like the Buckingham Fountain, one of the largest fountains in the world, and numerous art installations and sculptures.
The park is also the site for many of Chicago’s big events and festivals.
Fancy seeing Chicago from a new perspective? I highly recommend this private 45-minute helicopter tour. Expect sweeping views of the Windy City.
16. Visit the Museum of Science and Industry
Nestled in the Hyde Park neighborhood, this museum is one of the largest science museums in the world.
It’s an interactive museum that captivates visitors with its hands-on exhibits that cover topics ranging from space travel to vintage trains.
They even have a real U-505 German submarine from World War II that you can go onboard!
It’s particularly famous for its immersive experiences which include the Science Storms exhibit which reveals the science behind natural phenomenons.
17. Visit the historic neighborhood of Chinatown
This vibrant neighborhood, with its colorful storefronts and traditional Chinese architecture, offers a glimpse into the rich heritage of the Chinese community in Chicago.
As you wander through the streets, you’ll find a variety of shops selling everything from exotic spices to unique souvenirs.
One of the highlights is the delicious array of authentic Chinese cuisine available, from dim sum to Peking duck, offering a real taste of China in the heart of Chicago.
Chinatown can be overwhelming so I’d recommend this Chinatown food & walking tour.
It includes several tastings so you can taste a variety of different Chinese dishes and you’ll learn more about how Chinese culture has influenced Chicago.
18. Visit the scenic Promontory Point
This scenic garden, located inside Burnham Park, sits on a man-made peninsula that extends out into Lake Michigan, offering stunning views of both the lake and the city skyline.
Visitors can enjoy walking along the winding paths, sitting by the peaceful waters or having a picnic on the grassy lawns.
The park’s unique design, with its iconic limestone steps, makes it a favorite spot for relaxation and offers a welcome break from the city’s hustle and bustle.
19. Explore the vibrant and artistic Pilsen neighborhood
This vibrant area, known for its strong Mexican heritage, is decorated with stunning street murals that tell stories of community and history.
Strolling through Pilsen, you can explore local shops, art galleries and museums, such as the National Museum of Mexican Art, which showcases the beauty of Mexican art and culture.
The neighborhood is also famous for its authentic Mexican cuisine, offering a wide range of delicious dishes in cozy, family-run restaurants.
20. Walk through the historic Pullman District and visit the Pullman National Monument
This area was important in the late 1800s and early 1900s because it was a company town for the Pullman Palace Car Company, which made fancy railroad cars.
The Pullman National Monument is a museum where you can learn all about this history, see old buildings and understand how people lived and worked there.
It’s interesting for anyone who likes history or wants to see a different side of Chicago that’s not just about the big city and tall buildings.
21. Sample Chicago-style hot dogs from Portillo’s
Chicago-style hot dogs are unique because they’re loaded with a variety of toppings…
Yellow mustard, bright green relish, fresh chopped onions, juicy tomato wedges, a pickle spear, sport peppers and a dash of celery salt, all nestled in a poppy seed bun.
This combination gives a burst of flavors and textures with each bite.
Portillo’s, a beloved local chain, is famous for serving up some of the best versions of this iconic dish.
If you want to try a range of Chicago specialties then you should consider booking this Chicago Walking Food Tour!
You’ll get the chance to try Chicago’s famous hot dogs, deep-dish pizza, pastries and more whilst also seeing the best sights the city has to offer.
22. Visit Frank Lloyd Wright’s Home and Studio
Visiting Frank Lloyd Wright’s Home and Studio is a great way to explore the work of one of America’s most famous architects.
Located in the nearby suburb of Oak Park, this historic site is where Wright lived and worked for the first 20 years of his career. He actually designed the house himself.
Here, you can take a guided tour to see the inside of his home and studio, learning about his life and the unique design style that he developed.
It’s really interesting for anyone who likes architecture or wants to see something different near Chicago.
23. Experience the Chicago Symphony Orchestra at Symphony Center
The famous Chicago Symphony Orchestra is known for its incredible talent and the beautiful music it creates. They’re often hailed as one of the greatest orchestras in the world.
The Symphony Center itself is a grand building with amazing acoustics, making every note sound clear and powerful.
It’s a wonderful way to spend an evening, surrounded by the beauty of classical music in a stunning setting.
24. Explore the Garfield Park Conservatory
Located right in the heart of the city, the Garfield Park Conservatory provides a refreshing escape into nature, allowing you to escape the hustle and bustle of the city.
This large botanical greenhouse is filled with thousands of plant species from all over the world, creating a lush, green paradise.
It’s actually one of the largest greenhouse conservatories in the US!
As you walk through the different rooms, you’ll see everything from towering palm trees to delicate ferns and even a water lily pond.
25. Experience the Chicago History Museum
Located in the Lincoln Park neighborhood, the Chicago History Museum offers a variety of exhibits that showcase the city’s history, from its early days to modern times.
You’ll find interesting displays about Chicago’s architecture, the Great Chicago Fire and the city’s role in national events like the Civil Rights Movement.
It’s a fascinating place for anyone interested in history or wanting to know more about how Chicago became the city it is today.
26. Visit the Lincoln Park Zoo
This zoo, one of the oldest in the United States, is home to a wide variety of animals from all over the world, including lions, monkeys and penguins.
As you walk through the zoo, you can see these animals up close, learn about their habitats and understand more about wildlife conservation. They actually have more than 1,200 animals.
The best part is that admission to the zoo is free!
27. Discover the Shedd Aquarium
The Shedd Aquarium is one of the world’s largest aquariums and currently features around 32,000 animals.
This world-class facility houses an impressive range of aquatic life, from exotic fish to majestic beluga whales. You can even take part in shark feedings or meet penguins face-to-face.
My personal favorite highlight is the Abbott Oceanarium where you can get up close with dolphins, sea otters and seals.
28. Explore the Field Museum of Natural History
Located on Lake Shore Drive, this iconic museum is one of the world’s largest of its kind.
It features a range of impressive exhibits but the best one has to be “Sue”, the largest and most complete Tyrannosaurus rex skeleton ever found. She’s actually 67 million years old!
Visitors can delve into ancient cultures through the Egyptian tomb exhibit, explore the diversity of life in the Evolving Planet display or marvel at the dazzling display of gems and minerals.
I’d recommend booking your tickets online beforehand as this museum often reaches capacity. You can book your tickets here.
29. Enjoy the nightlife in Wicker Park
This trendy neighborhood is known for its diverse range of bars, live music venues and nightclubs, each offering something unique.
From cozy dive bars with a laid-back vibe to stylish lounges featuring local DJs, there’s something for every taste.
Wicker Park is also famous for its live music scene, showcasing both up-and-coming and more established bands.
30. Wander around Lurie Gardens
This 5-acre garden, which is located inside Millennium Park, was designed to showcase a variety of plants and flowers that change with the seasons.
Walking through Lurie Garden, you’ll see a blend of perennials, grasses, shrubs and trees which create a peaceful and colorful atmosphere. It feels like a secret garden!
The garden also features a wooden boardwalk and a shallow water stream that you can walk along.
31. Take a scenic drive along Lake Shore Drive
This iconic road winds along the lakefront, providing a front-row seat to Chicago’s stunning skyline, parks and beaches.
Whether you’re driving during the day or at night when the city lights up, the views are nothing short of breathtaking.
32. Explore the Museum of Contemporary Art (MCA)
The MCA features a diverse collection of modern art, including paintings, sculptures and multimedia installations.
It’s a great place to explore the latest trends in art and see the work and ideas of living artists.
The museum often hosts special exhibitions so there’s always something new to discover.
33. Check out the Chicago Botanic Garden
Located in Glencoe, just outside of Chicago, this large garden spans 385 acres and offers a stunning variety of plants and landscapes.
Tourists can explore various themed gardens, from Japanese gardens to colorful rose gardens, each providing a unique experience.
The garden also features serene walking paths, light displays, woodlands, tranquil lakes and even a waterfall.
34. Visit the DuSable Black History Museum and Education Center
This museum showcases a collection of artifacts, art and exhibits that celebrate the achievements and contributions of African Americans throughout history.
Tourists can explore galleries filled with sculptures, paintings and historical documents that tell powerful stories of resilience and progress.
It’s a must-visit destination for anyone who wants to learn about African American heritage and its impact on American society.
35. Visit the Japanese garden inside Jackson Park
This beautifully designed garden actually dates back to 1893 and was originally a gift from Japan. It symbolizes the long friendship between Japan and the US.
Today it serves as a peaceful oasis filled with lush pathways and koi-filled ponds.
The garden’s authentic tea house and serene waterfall also add to the Japanese aesthetic, making it a perfect spot for meditation or a peaceful stroll.
Insider Tip: Visit during the springtime and you’ll get the chance to see the famous cherry blossoms!
36. Experience Maxwell Street Market
This vibrant outdoor market comes alive every Sunday and has been taking place for 100 years.
Visitors can wander through rows of stalls selling a diverse range of goods, from vintage clothing and antiques to street food and fresh produce.
The market is also known for its live music and energetic atmosphere!
And that’s it!
Those are all of the best things to do in the Windy City.
From the heights of the Skydeck to the streets of the Magnificent Mile, this city is truly unique.