19 Best Things to Do in Chicago

Chicago, Illinois, is a cultural center of the USA and the perfect location for a fun-packed city break. With 77 neighborhoods to explore, world-class museums and galleries to visit, and lush green spaces and sprawling waterfronts to discover, you’re guaranteed to have an unforgettable time here.

Whether this is your first time visiting or you’re a regular in the Windy City, here are our 19 best things to do in Chicago.

1. Visit Garfield Park Conservatory

Garfield Park Conservatory showcases plants from around the world in a huge indoor space. The conservatory has eight display gardens — don’t miss the towering palm trees in Palm House or the indoor lagoon in Fern Room.

This tropical space is especially welcome if you’re visiting during the cold winter months, and advanced reservations are recommended year-round.

2. Go Museum Hopping

Chicago is one of the best cities in the USA to go museum hopping. Here are a few of the most fascinating establishments to check out during your visit:

• The Field Museum – a natural history museum located on the Museum Campus. This is the home of the largest and most complete Tyrannosaurus rex in the world.
• Adler Planetarium – America’s first planetarium. Head to the Telescope Terrace to observe the sky in great detail.
• Shedd Aquarium – home to 32,000 creatures, including penguins, sharks, tropical fish, and even beluga whales.
• The Museum of Science and Industry – the largest science museum in the Western Hemisphere. Come here for interactive exhibits covering all things science and technology.

3. See a Game at Wrigley Field

Wrigley Field is home to the Cubs and is one of the most iconic landmarks in Chicago. This ballpark was built in 1914 and some original features are still in action today. Catch a game to experience the electric atmosphere or take a tour to learn about this historic site.

4. Meet the Animals at Lincoln Park Zoo

Animal lovers shouldn’t miss a trip to Lincoln Park Zoo. The zoo is home to more than 200 unique global species and a well-established conservation and science program. Here, you can meet your favorite creatures safe in the knowledge that they’re being well taken care of.

The best part is that entry is completely free, so you can enjoy a family day out without breaking the bank!

5. Go Shopping on the Magnificent Mile

The Magnificent Mile is located on North Michigan Avenue and is the best place in the city to enjoy an afternoon of high-end retail therapy. Here, you’ll find more than 450 outlets, including luxury fashion labels, independent boutiques, and upscale malls.

These exquisite shopping experiences are not to be missed:

• Saks Fifth Avenue – fashion-forward apparel and unmatched service.
• Razney Jewelers – shop for custom jewelry and timepieces by Pakek Philipp and Rolex.
• 900 Shops – 70 luxury retailers across seven floors, including Gucci, Tesla, and MaxMara.

6. Discover the City’s Impressive Art Scene

As an internationally recognized cultural hub, it’s no surprise that Chicago offers an incredible range of art galleries. Whether you prefer modern art or the classics, add these three galleries to your sightseeing itinerary:

• The Art Institute of Chicago – one of the oldest and largest galleries in the country. See works by French impressionists such as Claude Monet and modern icons like Georgia O’Keeffe.
• Museum of Contemporary Art – this gallery sits at the cutting edge of art. Come here to admire modern and contemporary art in a wide variety of mediums.
• Addington Gallery – located in the River North area. Visit this gallery to see work by emerging local and international artists.

7. Stroll Along the Chicago Riverwalk

The Chicago Riverwalk is located on the south side of the Chicago River and is a vibrant waterfront place to shop, eat, and sightsee. Here are a few of the best things to see and do here:

• See public art – view permanent and temporary works by leading artists. Don’t miss Art on theMART which is the largest digital art projection in the world.
• Grab a bite to eat – head to the Riverwalk with an appetite to enjoy the many food and drink options on offer. City Winery’s patio is a popular spot for a drink and a bite on a sunny day.
• Take a boat tour – various tours run from May through October and include sightseeing tours, dinner cruises, and even kayak trips.

8. See a Show at The Second City

The Second City is where some of the best-known names in comedy — including Tina Fey and Bill Murray — got their start. There’s a variety of studios and stages showing everything from improv and up-and-coming comedians to scripted sketches and established acts. Book in advance to guarantee a seat.

Tip: Avoid booking front-row seats so you won’t have to crane your neck all night.

9. Snap a Selfie at The Bean

Cloud Gate, best known as The Bean is located in Millennium Park and is perhaps the most famous spot in the city to take selfies. The stainless steel sculpture was created by British artist Anish Kapoor reflects Chicago’s impressive skyline and is a must-see while you’re in town.

10. Eat a Deep Dish Pizza

Deep dish pizza is arguably the most famous food to have come out of Chicago, and no trip is complete without sampling a pie. You’ll have no trouble tracking one down, but here are three of the most popular spots that guarantee a fantastic cheesy feast:

• Burt’s Place – Anthony Bourdain called his experience here “the only deep dish pizza I’ve ever loved.” Pizzas come in various sizes with a half-dough option to cut down on the carbs.
• Louisa’s Pizza & Pasta – a no-frills pizza joint serving delicious deep dish. Choose your own toppings to create a unique pie.
• Kitchen 17 – vegans don’t have to miss out on the deep dish experience. Choose from toppings including seitan pepperoni, mac and cheese, or classic vegan mozzarella.

11. Cycle the Lakefront Trail

The Lakefront Trail makes a great escape from the hustle and bustle of the city. This 18-mile-long trail on the coast of Lake Michigan is popular with locals and visitors and can be explored on foot or by bicycle. The trail is open year-round but is at its best during the warmer spring and summer months.

12. Soak Up Green Mill’s Rich History

For classic Chicagoan nightlife with a side of history, Green Mill can’t be beaten. This jazz bar has attracted famous (and infamous) patrons over the years — Al Capone had a booth reserved here during Prohibition. These days, you’re unlikely to see any gangsters here, so swing by for live music and a nightcap.

13. Admire Chicago Architecture on a Boat Tour

Chicago’s skyline is an eclectic mix of design, and an architecture tour is the best way to fully appreciate it. Run by the Chicago Architecture Center, knowledgeable guides share information about the most interesting buildings along the Chicago River banks while you sail along on a luxury barge.

14. Attend a Music Festival

Chicago comes alive with music during the summer months, and the city is home to some of the best-loved festivals in the country. No matter what genre of music you’re into, you’re certain to find an event to attend.

Here are three of the very best that you’ll want to bag tickets for:

• Lollapalooza – an annual August festival featuring world-class artists such as The Killers and Megan Thee Stallion.
• Riot Fest – a three-day festival celebrating punk rock. Past performers have included Foo Fighters and The Cure.
• Chicago Jazz Festival – this free festival in Millennium Park and the Chicago Cultural Center celebrates jazz in all its forms.

15. Explore Artsy Wicker Park

Wicker Park is one of Chicago’s coolest neighborhoods and is the best place for thrifting, record shopping, and sipping coffee in trendy cafes. The best way to enjoy Wicker Park is to simply stroll around and soak up the atmosphere.

Three Wicker Park activities to check out on your walk are as follows:

• Eat southern food – Ina Mae Tavern serves some of the best Creole cuisine in the city. Don’t miss the po’boys and etouffee.
• Drink cocktails – The Violet Hour is a classy, award-winning bar serving artisan cocktails in a luxe setting.
• Thrift for vintage clothing – Vintage Underground is one of the city’s best-known spots for handpicked vintage clothing, accessories, and jewelry.

16. Take a Day Trip to Oak Park

Oak Park is less than ten miles from Downtown Chicago, and this charming, tranquil village welcomes a change of pace when the city gets too busy. As the former home of Frank Lloyd Wright and Ernest Hemmingway, architecture and literature fans will appreciate these fascinating tourist attractions:

• Frank Lloyd Wright Home & Studio – this home was the first project where Wright had complete creative control. He and his family resided here for 20 years.
• Ernest Hemmingway Birthplace Museum – Hemmingway was born here and the house is now an informative museum that explores his life and works.

17. Discover “Chicago’s Front Yard”

Grant Park, or “Chicago’s Front Yard,” is located in the Loop area and is often compared to New York’s Central Park. There’s plenty to see and do here — enjoy a picnic among the lush foliage, seek out the many statues and fountains, swing by a museum or gallery, or simply relax in the sun with a great book.

18. Admire the View at the Top of Willis Tower

For an unbeatable view of the Chicago skyline and beyond, pay a visit to the Skydeck. Head up to the 103rd floor of the Willis Tower where, on a clear day, it’s possible to see four states across the Midwest.

For an extra thrill, take a walk on The Ledge — a glass platform that juts out from Willis Tower. Just 1.5 inches of glass stand between you and the ground over 400 meters below, so this isn’t for the fainthearted!

19. Spend an Evening on the Navy Pier

Navy Pier is a huge waterfront playground where locals and visitors head to dine, shop, and be entertained. An exciting year-round program of special events takes place on Navy Pier, so check the website to see what’s happening during your time in Chicago.

Be sure to check out these three hotspots no matter when you visit:

• Centennial Wheel – see the Chicago skyline from 200 feet up on this waterfront Ferris wheel.
• Offshore Rooftop – the largest rooftop deck in the country. Head here to eat and drink with unmatched Lake Michigan views.
• Chicago Sports and Novelty – pick up merch from Chicago’s top sports teams including the Bears and the Cubs.

Discover the Many Fun Things to Do in Chicago

Chicago is a sprawling American metropolis that offers visitors an eclectic array of activities and attractions. You’ll never be short of exciting things to do in the Windy City. What’s at the top of your to-do list during your next Chicago adventure?