20 Things to Do in Chicago for an Unforgettable Visit

Chicago’s got a little bit of everything—art, history, outdoor fun, and plenty of surprises. Whether it’s your first time or you’re back for another round, there’s always something unexpected waiting around the corner.

From iconic sights to hidden gems, much like the charming adventures you’ll find when exploring things to do in Paris, the city promises a unique experience. Whatever your pace, you’ll find things to do that fit your mood and style. Here are 20 ways to dive into Chicago and make your trip one for the books. 

Fun Things to Do in Chicago

Chicago is packed with iconic spots, cool experiences, and unique sights. Whether you’re into art, architecture, or just want to explore the city’s vibe, here are a few must-do activities:

1) Visit The Art Institute of Chicago

The Art Institute of Chicago is packed with art from every era, tucked downtown near Millennium Park—so it’s easy to swing by. You don’t have to be an art expert to enjoy it, either.

Check out “The Assumption of the Virgin” or the tiny, intricate Thorne Miniatures. Even if you’re short on time, there’s plenty to catch your eye.

Source: IG(artinstitutechi)

2) Stroll through Millennium Park

Millennium Park is open daily, early morning till late at night, and it’s hard to miss if you’re downtown. Public art, green lawns, and people-watching—what’s not to like?

The Bean (technically Cloud Gate) is basically selfie-central. There’s also the quirky Crown Fountain, which is fun on a hot day.

If you’re into art, the outdoor walking tour (April to October) is worth a look. Sometimes you’ll stumble on a free concert at the Jay Pritzker Pavilion, too.

Source: IG(only_chicago)

3) Explore Navy Pier

Navy Pier is right on the water and always buzzing. There’s food, shops, and enough attractions to keep you busy, rain or shine.

Take a spin on the Ferris wheel or catch an outdoor movie or live music. It’s a classic spot to kick back and soak in the skyline.

Source: IG(navypierchicago)

4) Walk the Chicago Riverwalk

The Riverwalk runs 1.25 miles through downtown, giving you a front-row seat to the city’s architecture. It’s a nice break from the bustle up above.

Grab a coffee, check out some public art, or just sit by the water. If you’re feeling adventurous, hop on a boat tour or rent a kayak for a different view.

Source: IG(insta_chicago)

5) Discover the Field Museum

The Field Museum is a treasure trove of natural history—dinosaurs, mummies, and oddities you didn’t know you wanted to see. With 24 million objects, it’s easy to lose track of time.

Open daily, it’s good for all ages and has plenty of hands-on exhibits. You’ll walk away with a few new facts, guaranteed.

From the story of life on Earth to rare artifacts, it’s a must for anyone who’s even a little bit curious.

Source: IG(modluxweddingschi)

6) Check out Shedd Aquarium

Shedd Aquarium is home to over 70 species—sea turtles, sharks, stingrays, you name it. The big round tank is mesmerizing with all its colorful coral and fish darting around.

There are animal encounters (like meeting a sea otter!) and interactive programs if you want to get more involved. It’s a fun way to learn about the underwater world without getting wet.

Source: IG(allih26)

7) Experience the Museum of Science and Industry

This museum is all about getting your hands dirty—in a good way. Science Storms lets you feel hurricane-force winds, and there’s even a real submarine you can check out.

Live experiments and hands-on activities make every visit a little different. If you’re curious by nature, you’ll probably love it here.

Source: IG(danfarrow9)

8) Shop along The Magnificent Mile

The Magnificent Mile is Chicago’s go-to shopping stretch. Luxury brands, popular stores, and a whole lot of window shopping—there’s something for everyone.

Water Tower Place is a landmark stop, and you’ll find plenty of places to grab a bite or catch a show between shops.

Source: IG(sairakahn_)

9) Catch a show at Chicago Theatre

Chicago Theatre is a downtown icon with its glowing marquee. It hosts concerts, comedy, and Broadway shows in a space that feels special the second you walk in.

Check the lineup ahead of time and grab tickets online. It’s a classic night out, whether you’re into music or just want to see the inside of the theater.

Source: IG(brenda_summerville_)

10) Enjoy deep-dish pizza at Giordano’s

If you’re in Chicago, deep-dish pizza is non-negotiable—and Giordano’s is a local favorite. Their pies are thick, cheesy, and loaded with toppings.

They’ve been at it since 1974, and you can grab your pizza to go if you’d rather eat in your hotel room. The sausage deep-dish is a crowd-pleaser, just saying.

Source: IG(giordanospizza)

11) Take an architecture boat tour

Seeing Chicago from the river is a whole different experience. The architecture boat tours are both relaxing and surprisingly interesting, even if you’re not a history buff.

You’ll spot landmarks like the Willis Tower and Wrigley Building and get the backstory on how the city came together. Honestly, it’s hard not to be impressed by that skyline.

Source: IG(chicagoriverboattours)

12) Visit the Chicago History Museum

This museum digs into Chicago’s past—sports, politics, the Great Fire, and more. It’s kid-friendly and has interactive exhibits that make history less, well, boring.

Illinois residents can get in free on certain holidays. There are also tours and events if you want to go deeper into the city’s story.

Source: IG(chicagomuseum)

13) Relax at Grant Park

Grant Park is perfect for a slow stroll or just sitting on a bench, people-watching. The fountain is a highlight, especially when it’s all lit up.

Sometimes you’ll catch a free concert or wander over to the Art Institute nearby. It’s a good place to catch your breath in the middle of the city.

Source: IG(chicago.explore)

14) Explore Lincoln Park Zoo

Lincoln Park Zoo is free and open every day, which makes it an easy choice. It’s got lions, gorillas, meerkats, and more, all just a stone’s throw from downtown.

There are quick daily activities for all ages, and you can use their web app to plan your route or learn about the animals. Handy!

Source: IG(starberry1984)

15) Explore the Garfield Park Conservatory

The Garfield Park Conservatory is massive and full of plants from all over the world, all under one roof. It’s free to enter and feels like a little escape from the city noise.

Check out their events and art programs if you’re in the mood for something different. It’s a peaceful, green spot that’s easy to love.

Source: IG(gpconservatory)

16) Visit the Adler Planetarium

Adler Planetarium is the place to go if you’re even a little bit curious about space. The live sky shows are surprisingly cool, and the presenters make it feel personal.

Exhibits cover things like the Ring Nebula, and you don’t have to be an astronomy buff to enjoy it. It’s a fun, low-pressure way to get your head in the stars.

Source: IG(suguscircle)

17) Tour the Chicago Cultural Center

The Chicago Cultural Center offers free tours that spotlight its stunning architecture—think domes, mosaics, and a whole lot of history. The building itself is a work of art.

Whether you go in person or check out a virtual tour, you’ll pick up stories that make you see the city differently. It’s a quiet gem in the middle of downtown.

Source: IG(chicagoculturalcenter)

18) Sip craft beers at Revolution Brewing

Revolution Brewing is a local favorite for a reason. Their taproom is lively, and the beer list is always changing—there’s usually something new on tap.

You can hop on a brewery tour or just hang out for one of their special events. It’s a chill spot, whether you’re a beer nerd or just want to unwind for a bit.

Honestly, if you’re looking to sample Chicago’s craft beer scene, this is a solid place to start.

Source: IG(revbrewchicago)

19) Discover local wines at City Winery

City Winery in the West Loop is where wine and live music meet. The vibe is relaxed, with local wines and creative food on the menu.

Come for a tasting, stick around for a show, or just enjoy dinner with friends. They host comedy and music nights, too.

It’s great for a night out or even a private event if you’re celebrating. The atmosphere feels a bit special without being stuffy.

Source: IG(citywineryriverwalk)

20) Try the Italian beef sandwich at Al’s Beef

If you haven’t tried an Italian beef sandwich, Al’s Beef is the spot. The beef is juicy, the au jus has a kick, and you can pile on toppings like provolone or spicy giardiniera.

Al’s has been around forever, and it’s a classic stop for a reason. Messy? Sure. Delicious? Absolutely.

Source: IG(alsbeef)

Planning Your Chicago Adventure

When you’re planning, timing is everything—weather and local events can really shape your trip. Figuring out how to get around ahead of time saves you headaches and lets you pack in more fun.

Best Times to Visit

Spring and fall are usually the sweet spot—mild weather, fewer crowds, and the city feels a bit more relaxed. Perfect for wandering neighborhoods or hanging out in parks.

Summer is festival season and the energy is high, but it gets crowded and prices jump. Winter? It’s cold, sure, but there are holiday markets and fewer lines everywhere.

If you can, time your visit with big events like Taste of Chicago in July or the Christmas Market in December. It’s a good way to see the city at its best.

Source: IG(chicago.explore)

How to Get Around the City

Chicago’s public transit—the ‘L’—is cheap and covers most places you’ll want to go. Grab a Ventra Card for easy access to buses and trains.

Downtown is walkable, especially the Loop and River North. For longer trips, rideshares and bike rentals are quick options.

If you’re taking transit a lot, get a day or multi-day pass to save some cash. Parking is pricey and tricky, so unless you love a challenge, stick with public transport.

Whether you’re exploring Chicago or thinking about places like Austin, Texas, it’s all about finding things that make your trip enjoyable and special.

Tips For Making the Most of Your Visit

Getting the most out of Chicago is all about planning smart and blending in a bit. Knowing where to find deals on tickets and picking up on local habits can make your trip smoother—and a lot more fun.

Saving Money on Attractions

If you’re looking to save a few bucks, think about grabbing a multi-day CTA pass. It’s good for unlimited rides on trains and buses, and honestly, it’s way more affordable than paying for each trip. Plus, you’ll have no trouble getting to places like Millennium Park or the Museum Campus without worrying about fares every time.

Some attractions actually have free or discounted entry on specific days or evenings. For example, a few museums open their doors for free during certain hours. It’s worth checking their websites before you go—sometimes you get lucky.

Another trick? Book combo tickets or city passes ahead of time. These usually bundle big-name sights—like river boat tours and sky-high observation decks—into one deal, and you’ll often pay less than if you bought each ticket on its own. Not a bad way to stretch your budget.

Local Etiquette and Customs

Chicagoans tend to favor direct, polite conversation. If you’re on public transit or just out walking, try to keep things moving—don’t block the flow, and step aside if you need to stop.

Tipping’s pretty much the norm at restaurants and bars, usually around 15-20%. For bigger groups, double-check your receipt since a service charge might already be added.

In formal situations, it’s common to use “sir” or “ma’am.” Most locals are friendly and will chat if you need directions or have a question—just ask nicely and you’ll probably get a smile.

Jaywalking? Not a great idea downtown. Wait for the crosswalk signal, since the city actually enforces those pedestrian rules.