The Windy City is a bustling metropolis brimming with activities and attractions.
From world-renowned museums to stunning architecture, vibrant arts scenes, and diverse culinary experiences, Chicago offers something for everyone.
Whether you’re an art enthusiast, a history buff, a food lover, or someone who loves the outdoors, Chicago has a wealth of experiences waiting for you.
Now, I actually grew up in Chicago, and on a recent visit, I was reminded just how underrated this city is.
So as a Chicago native and a travel expert all the cool things to do in Chicago that will make your visit unforgettable.
And before you visit the third largest city in the United States, check out if Chicago is safe to visit in 2024.
Fun & Best Things to Do in Chicago
When you’re not strolling along the iconic Lake Michigan or exploring the city’s unique neighborhoods, you’ll find an array of activities that will fill your Chicago weekend itinerary (or beyond) with excitement and discovery.
Chicago’s rich cultural heritage, impressive skyline, and dynamic food scene make it a prime destination for any traveler.
Here’s a comprehensive list of activities that ensure you won’t miss a beat while exploring this vibrant city.
#1 Relax at Grant Park
“Chicago’s front yard,” Grant Park, is a 300-acre park in the middle of downtown Chicago.
Many must-see attractions on this list, such as Millennium Park and The Art Institute of Chicago, can be found in Grant Park.
The park hosts numerous attractions and events and has plenty to do.
You can take a stroll through the park’s gardens, bike along The Lakefront Trail, or even utilize sports facilities such as the tennis and softball courts.
On our recent trip, Scott and I loved walking through the park and all the green areas!
As for landmarks, visit the Buckingham Fountain or explore the Museum Campus. Other well-known landmarks include the Field Museum, Shedd Aquarium, and Adler Planetarium.
Grant Park is also the site of many festivals, including the famous Taste of Chicago and the Grant Park Music Festival.
#2 Explore the Art Institute of Chicago
Art lovers should not miss the Art Institute of Chicago, home to an art collection with world-class variety.
You’ll find it in downtown Chicago, just south of Millenium Park. With thousands of pieces on show, you can spend a good chunk of the day there.
You can find works from esteemed artists like Monet, Picasso, and Van Gogh, as well as centuries worth of different art styles, from ancient artifacts to contemporary masterpieces.
The museum’s standout pieces include works from Grant Wood, such as “American Gothic.”
Georges Seurat’s world-famous “A Sunday on La Grande Jatte” and Claude Monet’s Impressionist piece “Water Lilies” are also included.
You can buy tickets on the Art Institute website; however, they’re closed on Tuesdays and Wednesdays.
#3 Walk the Magnificent Mile
The Magnificent Mile is Chicago’s premier shopping district, stretching along Michigan Avenue from the Chicago River to Oak Street.
Here, you can shop at high-end retailers, dine at award-winning restaurants, and marvel at the historic architecture.
Don’t miss Water Tower Place, a shopping mall with over 100 stores in a multi-level layout.
There are also places to eat, like The Purple Pig, a Mediterranean restaurant with an open kitchen.
What’s more, you’ll see cultural sights like the Tribune Tower — a neo-Gothic skyscraper and former home of the Chicago Tribune Newspaper.
And once you see the Tribune Tower in person, your jaw will drop — mine did haha! It’s just that beautiful.
Overall, the Mag Mile is a perfect spot for sightseeing, window shopping, snacking, and serious retail therapy.
#4 Indulge at the Chicago French Market
Located in the Ogilvie Transportation Center, the Chicago French Market is a food lover’s paradise.
The European-inspired indoor food market has over 30 vendors offering a variety of gourmet foods, fresh produce, and artisanal products.
The market’s vibrant and bustling atmosphere, combined with its colorful displays of pastries, cheeses, flowers, and more, makes it a great place for snapping photos.
You can find cuisine from around the world, including French, Italian, Japanese, Mexican, and more.
Whatever you’re in the mood for, be it sweet treats, snacks, or a filling meal, there’s something to satisfy every craving.
Try a poke bowl from Aloha Poke or indulge in a sweet treat from Vanille Patisserie while soaking in the market’s lively vibe.
#5 Cruise the Chicago River
One of the best ways to see Chicago is from the water.
If you love history and architecture, then this is one of the best activities in Chicago to explore and learn about the city’s buildings.
The Chicago Architecture Foundation River Cruise is highly recommended for its informative and engaging tours of the city’s architectural highlights.
As you glide along the Chicago River, you’ll learn about the history and design of iconic buildings like the Willis Tower, Tribune Tower, and Marina City.
You’ll hear stories behind more than 50 buildings along the Chicago River.
The cruise lasts for an hour and a half.
Ticket prices start at $54, and you’ll meet at the northeast corner of Michigan Ave and E. Wacker Dr near the black awning marking the stairway entrance.
#6 Experience the Chicago Theatre
Head to the historic Chicago Theatre, a beautiful venue known for its iconic red and yellow marquee and grand architecture.
Situated on North State Street, the theater first opened in 1921 and has hosted big names like Prince and Diana Ross over the years.
Whether you’re into Broadway productions, concerts, comedy shows, or special events, the Chicago Theatre offers diverse performances that cater to all tastes.
The theater’s interior is just as impressive as its exterior, so take a moment to admire its lavish design.
If you want to book to see a performance soon, be sure to get tickets from their website here.
#7 Dine in the West Loop
The West Loop is Chicago’s culinary hotspot, home to some of the city’s best restaurants.
Explore Randolph Street, known as “Restaurant Row,” and discover a range of dining options from upscale eateries to casual spots.
There are plenty of spots to visit. There are lovely cafés like Sawada Coffee and The Allis where you can get premium coffee and sit in well-decorated and cozy seating.
Some notable restaurants include Girl & the Goat (small plates), Au Cheval (diner-style burgers), and The Publican (beer, pork, and oysters).
These are just some options on the West Loop, so be sure to explore more while out and about.
#8 Visit the Field Museum
Situated in the heart of Chicago’s Museum Campus, with Shedd Aquarium and Adler Planetarium nearby, the Field Museum is an expansive natural history museum, one of the biggest in the world.
If you’re into science and natural history, you should definitely visit this museum.
When I was a kid, I literally grew up going to the Field Museum and collecting the little wax figures you can make there.
Even as an adult, it’s so fun to explore, and I highly recommend it!
The museum’s extensive collections include Sue, the largest and most complete T-rex skeleton ever discovered, as well as fascinating exhibits on ancient Egypt, the Americas, and more.
There’s an extensive collection of gems, meteorites, fossils, books, animal exhibits, and even working labs like the DNA Discovery Center, where you can watch scientists at work.
Since there are so many things to see, plan to spend several hours exploring the vast array of artifacts and displays.
Tickets are available on the Field Museum Website. Note that the all-access pass includes access to all ticketed exhibitions.
The discovery pass gives you basic admission plus the choice of a one-ticketed experience. Basic admission includes general admission exhibitions.
#9 Sip Coffee at Mindy’s Bakery
Mindy’s Bakery is a haven for anyone with a sweet tooth and a love for artisanal baked goods.
Founded by James Beard Award-winning pastry chef Mindy Segal, the bakery has quickly become a local favorite, known for its innovative treats and inviting atmosphere.
The bakery offers an impressive selection of pastries, breads, cookies, and more.
From flaky croissants and sugary donuts to hot fudge babkas and blueberry ‘Pop-Tarts,’ there’s something to satisfy every craving.
Mindy’s is particularly renowned for its bagels, which are hand-rolled and boiled to perfection.
You can also get a selection of coffees, teas, and other beverages along with your baked goods.
#10 Admire the Views from the Skydeck
If you’re looking for an adrenaline-spiking Chicago activity, you should check out the Skydeck.
You will be able to access the Skydeck on the 103rd floor of the Willis Tower (formerly Sears Tower), which offers unparalleled views of Chicago.
If you’re not scared of heights or just want a thrill, step out on “The Ledge.”
The Ledge is a secure glass balcony that extends four feet outside the building. Experience the exciting opportunity of seeing the city from 1,353 feet above ground.
On a clear day, you can see up to four states from the Skydeck, making it a must-visit for breathtaking panoramic views.
#11 Grab a Glass of Wine at The Book Cellar
Nestled in the charming Lincoln Square neighborhood, The Book Cellar is a beloved independent bookstore with more going for it than just books.
This cozy spot is perfect for book lovers who want a quiet place to relax with a good read.
The store also regularly hosts a variety of events, including author readings, book signings, poetry nights, and book clubs.
What sets The Book Cellar apart is its in-store café.
Sip on a lovely cup of coffee, beer, or wine while reading. The café also serves light snacks, sandwiches, and pastries, making it an ideal spot for a leisurely afternoon.
#12 Visit Millennium Park
Housed within the larger Grant Park, Millennium Park is a must-see for any visitor to Chicago.
The park is a hub for art, architecture, and music, with free concerts and events held year-round.
This urban oasis in the city’s heart features iconic landmarks, one of the most famous being Cloud Gate (affectionately known as “The Bean”), a 110-ton reflective sculpture made out of stainless steel and shaped like a bean.
However, that’s not all the park is known for.
Crown Fountain is another standout attraction. Made of two 50-foot blocks sitting on each end of a shallow, reflective pool, the fountain is a large rectangular interactive feature.
The video the sculpture projects shows images of passing citizens, creating a magical experience.
Finally, you certainly won’t miss the Jay Pritzker Pavilion, the park’s centerpiece and home to many musical performances throughout the year.
#13 Drive the Gold Coast
Okay, can we quickly talk about Chicago’s Gold Coast?
This is a historic district in the city that is beloved for its lakefront views.
On my last visit to Chicago just driving the famous Lakeshore Drive brought me back all the feels — it’s so vibey with the towering buildings and lake Michigan lining the street.
It’s super magical when the sun starts to go down.
Like you kind of feel like you’re in California, but it’s a lot greener and most historic — hard to describe!
I love it, and trust me, you will too.
For the best views, I recommend driving Lakeshore Drive north!
What to Do in Chicago FAQ
You may still have some questions about visiting Chicago and what to do there.
Here are some commonly asked questions and their answers about Chicago and its attractions.
What Is the Best Time of Year to Visit Chicago?
The best time to visit Chicago is during the spring and fall when the weather is still lovely, and there are a variety of festivals and events.
Summers can be busy and warm, but many festivals are ongoing, while winters are cold with the potential for snow.
Is Public Transportation Available in Chicago?
Yes, Chicago has an extensive public transportation system operated by the Chicago Transit Authority (CTA).
The “L” trains and buses provide convenient and affordable ways to get around the city.
Additionally, you can take taxis and rideshares like Uber and Lyft or opt for bike rentals, which are widely available.
Are There Free Things to Do in Chicago?
Absolutely! Many of Chicago’s top attractions, including Millennium Park, Lincoln Park Zoo, and the Chicago Cultural Center, offer free admission.
You can also enjoy free concerts, festivals, and events throughout the year — The Grant Park Music Festival and the Chicago Blues Festival are just two examples.
What Are Some Must-Try Foods in Chicago?
Chicago is known for its variety of tasty foods.
Some must-try foods include the famous Chicago-style deep-dish pizza from places like Lou Malnati’s or Giordano’s.
Other must-try’s include a Chicago-style hot dog from Portillo’s. Try their chili cheese dog or their plant-based Gardendog “dragged through the garden.”
Then you have to try a proper Italian beef sandwich from Al’s Beef.
Finally, when it comes to dessert, don’t forget to try a slice of Eli’s Cheesecake and Garrett Popcorn’s Chicago Mix for a sweet treat.
Chicago Things to Do Wrapped Up
There you have it: a guide to the best things to do in Chicago.
From Millenium Park to the West Loop, explore the city’s world-class museums, take in the captivating architecture, enjoy a river cruise, or indulge in the diverse culinary scene.
Each neighborhood and attraction provides a unique glimpse into the city’s vibrant culture and history.
From relaxing in Millennium Park to marveling at the views from the Skydeck, your time in Chicago will be filled with unforgettable moments and discoveries.
So, go ahead and start planning your trip to the Windy City.
Read Next: Looking for more places to visit and things to do? Check out these Instagrammable places in Chicago next.
