32 Of The BEST Most FUN Things To Do In Chicago
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Founded in 1837, Chicago has been captivating all that visit with beautiful and bold ideas pushing architectural and entertainment boundaries for nearly 200 years! Sitting right on the banks of Lake Michigan, this city twists and evolves as drastically as Chicago’s four seasons do. Where else in the world can you enjoy a beautiful summer stroll along the Chicago Riverwalk and, a few months later, witness a full blizzard from atop one of the tallest buildings in the world? Only in Chicago.
Chicago is one of the best cities in the United States when it comes to sights and entertainment. You could easily spend a full week in the windy city and still be left with so much to see and do. With great sights like the giant, open Lincoln Park. One-of-a-kind architecture, both old and new, like the Marina City Towers and Chicago Tribune. Spectacular offerings at Rooh and other world-class restaurants in Chicago. Plus, tons of entertaining activities scattered around the city, from sky-high observation decks to historic ballparks, and a stunning river right at the center. This magnificent city really has it all!
In a city with thousands of awesome activities to check out, here are the absolute BEST THINGS TO DO IN CHICAGO!
1.) Chicago Botanic Garden
Covering a staggering 385 acres, this massive garden is as peaceful as it is diverse. With multiple large ponds and, of course, stunning floral displays dispersed all about. You can spend an entire day at the Chicago Botanical Garden and still not see everything. Plus, rotating arrangements that change with the seasons help keep the park fresh throughout the year.
Pro tip- Don’t forget to stop by the butterfly garden to see an entire enclosure filled with butterflies from around the world. 🦋
2.) 360 Chicago Observation Deck
On the other side of downtown as the Willis Tower Skydeck, this viewpoint shows a whole new side of Chicago. At 1030 feet tall, the 360° observation deck grants you stunning views over the north side of the city, the coast of Lake Michigan, and on a clear day, 4 nearby states!
Pro tip- As you make your way to the elevator, stop and check out the brief interactive experience showing what makes up Chicago.
3.) Lincoln Park
Found on the north side of the city, Lincoln Park and its multiple square miles of open green space and beautiful ponds stand as the true epicenter for everything outdoorsy in Chicago. Be it the dozens of walking paths, basketball courts, a golf course, farmers markets, even a couple beaches, there’s always something going on at this gigantic park.
Pro tip- Stop by the People’s Gas Pavilion for one of the best picture spots in the city.
4.) A Chicago White Sox Game At Guarenteed Rate Field
While the White Sox may feel like Chicago’s forgotten sports franchise, the long and deep-rooted history still provides plenty of reason to catch a game. Found on the other side of town as the Cubs, this franchise is home to an entirely different set of fans with an entirely different atmosphere, but one that’s still pure baseball and pure Chicago. So, if you’re looking to take in some baseball and some rich baseball history at a much more affordable price, then the South Side Sox is the place to go.
Pro tip- For everything you need to know, check out our full ballpark guide! (Coming Soon)
5.) Garden Of The Phoenix
A true hidden gem of Chicago, so much so that most people don’t even know this place exists! The Garden of the Phoenix is a quiet pond on the opposite side of the Museum of Science and Industry, perfect for enjoying the outdoors within the city. Still water sprinkled with hundreds of bright green lilypads makes this one of the more underrated picture spots in Chicago.
Pro tip- Mornings here, before the city comes to life, are a spectacular start to the day. 🌅
6.) American Writers Museum
Travel through the history of American writers, from the forefathers and the birth of the Declaration of Independence all the way to the writers of the present. See dozens of incredibly influential authors who shaped the United States into the country it is today. You may even be inspired to write something of your own.
Pro tip- Before you leave, check out the machine by the exit that prints off tiny excerpts of powerful, famous writings to get you into a creative mood.
7.) Shedd Aquarium
Regarded as one of the best aquariums in the country, Shedd Aquarium is packed to the gills (sorry) with tons of different exhibits that have been capturing imaginations for almost 100 years. Spanning across all forms of aquatic life, from big beluga whales swimming around giant tanks to petite seahorses hiding among the seagrass, all the wonders of the ocean can be found right in Chicago at Shedd Aquarium!
Pro tip- Try a CityPASS to see Shedd Aquarium and other great things to do in Chicago, while saving some money.
8.) Museum Of Science And Industry
For anyone interested in having a good time while also learning something new, the many different wings of the Museum of Science and Industry are the place to go. Full of diverse sections like the area showing the science behind storms with a tall tornado simulator, the history of toys with plastic mold machines, and the transportation gallery with full-scale planes and trains. With tons of fun exhibits and interactive displays, this building is part museum, part educational playground.
Pro tip- Paying for the additional exhibits like the U-505 and rotating galleries is well worth the added fees.
9.) Cloud Gate aka The Chicago Bean
No stop to Chicago is complete without stopping at the world-famous sculpture. Built in 2004, this massive 110-ton art installation was made to be a gate blending the sky and the viewer. Seeing the city’s skyscrapers reflect off Cloud Gate’s iconic oblong sculpture is as Chicago as it gets.
Pro tip- Get to Cloud Gate early in the morning to get some great pictures and avoid the massive crowds. 👍
10.) Taste The Original Brownie At The Palmer House
Found in the Chicago Loop, the gorgeous and elegant Palmer House opened in 1873, is the oldest continuously operated hotel in the country. While the grand, stunning gold finish interior designs are very well known throughout the area, perhaps something even more memorable can be found not on the walls or staircases but on a plate. Home to the first ever brownie, the Palmer House has been treating people to its chocolatey creation for over 130 years!
Pro tip- Head to the Lockwood Express inside the hotel if you want to try this treat but don’t have time for the full sit down dessert.
11.) U-505 Museum
While technically located inside the Museum of Science and Industry, the U-505 area feels like an entire museum itself. Centered around 1 of only 4 German U-boats that remain in the world today. This 252-foot-long vessel surrounded by the history of WW2 and the harrowing story of how this boat was captured is one of the most unique things you can do in Chicago.
Pro tip- Take the U-505 tour to explore the inside of the submarine and get a full experience of what it was like during the war.
12.) Lincoln Park Zoo
No city in the United States is complete without a zoo, and in Chicago, the Lincoln Park Zoo is better than most. With enclosures from across the globe like African animals, penguins and primates, plus large grass ponds full of exotic birds, this smaller sized zoo is home to a large look at the animal kingdom. And the best part… it’s FREE!
Pro tip- There are also plenty of other free activities like feedings and up close care of various animals.
13.) Navy Pier
Navy Pier is a refreshing feel to the Midwest city. Bringing in a fun port city or oceanfront kind of element to Chicago. Feel the lake breeze as you explore shops, restaurants, and a giant Ferris wheel with the great city skyline in the distance. At Navy Pier, there’s something entertaining for everyone and an even better lake view to go along.
Pro tip- The best view of the pier and city skyline is at the top of the Ferris wheel. Try a CityPASS to save a couple of bucks and reserve your tickets now!
14.) Chicago Sports Museum
What does an exploded baseball, x-ray pictures, and championship rings have in common? All of these unique pieces of memorabilia can be found here at the top of the Water Tower Place. Chicago is one of the most historic sports cities in the country with unforgettable moments spanning well over a century. From iconic franchises and legends of the game to defining moments that captured the entire country’s attention, at the Chicago Sports Museum, you can see all of the best and so much more!
Pro tip- If you buy 2 drinks at Harry Caray’s bar your ticket is free. 🍻
15.) Buckingham Fountain
Nearly 1 century old, this massive and extravagant fountain is another striking example of Chicago’s creative achievements. Sandwiched between Millennium Park and Shedd Aquarium this aquatic display shooting water up to 150ft in the air is a great place to relax and take in the city. Add in the city skyline in the background, and you get another excellent place for pictures.
Pro tip- Stop by at night to see the water lit up in different colors as the city shines in the distance.
16.) Second City Chicago
Since 1959, Second City has been regarded as one of the premier comedy centers in the world. Here you can enjoy different hilarious shows or try your hand at some acting/comedy classes on the same stage where names like Bill Murray, Dan Aykroyd, Steve Carell, John Candy and many other comedy legends all got their start. So if you want to relax and enjoy some laughs, a mecca of comedy, acting, and anything show biz is the place to go.
Pro tip- Check out their schedule to see all the best shows!
17.) Willis Tower Skydeck
The former tallest building in the world for almost 25 years. Whisked up 103 floors from the ground, so high up that people below look like ants scurrying around the Chicago streets. Plus, a glass box protruding out of the building with see through walls and floor so you can see straight down the side of the iconic Willis Tower. Need we say more?
Pro tip- Buy the Expedited Entry ticket. Skipping all the long lines is well worth the couple extra bucks.
18.) Millennium Park
Known as the unofficial creative center of Chicago, Millennium Park is packed with unique sights unlike any other. Art installations like Cloud Gate, Crown Fountain, and Lurie Garden all showcase the artistic accomplishments that have made Chicago so world-renowned. Whether you’re looking for inspiration or simply a pleasant place to walk around, Millennium Park is a must when in Chicago.
Pro tip- With all of these well known sights in the same spot, Millennium Park can get pretty crowded. Your best bet is to get there in the early morning, which also makes for great picture opportunities!
19.) Gold Pyramids Of Illinois
Egypt in the American Midwest? In this combination that makes sense to nobody, colossal Egyptian-like pyramids and 50ft tall statues of King Tut rise up in the middle of nowhere. It may be odd and confusing, but the over 100 true-to-life ancient Egyptian replicas are an interesting spectacle nonetheless. While everyone hits the usual Chicago hotspots, why not try one of the most out of place attractions in the American Midwest?
Pro tip- If you’re looking for even more Gold Pyramid randomness, you can try some of their signature water and vodka.¯\_(ツ)_/¯
20.) Chicago Mural Mile
Continuing the windy city’s artistic flair, over a dozen clean works of art decorate concrete walls and overpasses of the Red Line track in the Rogers Park neighborhood. Started in 2007, this collection of images tell stories of the city and surrounding parks, covering history from the present all the way back to their Native American roots. Like a walking outdoor mural museum whose powerful designs both educate about the past and inspire for the future.
Pro tip- Head to N Glenwood Ave & W Estes Ave for the best of the street art.
21.) Indulge In One Of The Best Food Cities In The Country
East to west, north to south, there are gourmet meals galore when it comes to the windy city. Everything from outstanding fine dining to thick crust Chicago style deep dish pizza. You may not think of Chicago as a culinary powerhouse, but you certainly will after you sample some of the best restaurants in the United States.
Pro tip- Check out all of the best restaurants in Chicago here!
22.) See The Most Picturesque Spots
Believe it or not, but Chicago is actually one of the most photogenic cities in the world! A city where towering skyscrapers meet glistening water that cuts through the center of downtown. Packed with secluded spots and bustling bridges all forming fabulous Instagramable spots gorgeous enough to make everyone jealous!
Pro tip- Want to see the most amazing picture spots in Chicago? Check them all out here!! 
23.) Chicago Magnificent Mile
Caught a bit of the shopping bug? Then there’s no better place to go than the Magnificent Mile. See the glitz and glamour of Chicago with hundreds of stores, from flashy designer clothing to small gourmet cafes. In what’s known as the shopping center of the city, you’re guaranteed to find whatever you’re looking for and so much more!
Pro tip- Head to Water Tower Place for 74 stories of the best shops and restaurants on Magnificent Mile.
24.) Garfield Park Conservatory
Over 100 years old and a groundbreaking work of art at the time, the Garfield Park Conservatory is so much more than a collection of greenhouses. It’s a plant filled paradise. Exotic species gathered from around the globe, arranged in gorgeous botanical displays, all bursting with vibrant colors and extravagant patterns. Even if you’re not big into botany, it’s still an awesome place to relax and explore something different. And it’s free to enter; you can’t beat that.
Pro tip- Make sure to stop by the Fern Room. A whole wing resembling an overgrown jungle filled with thousands of ferns, a large coy pond, and a mini waterfall. Plus, a great spot for some cool photos. 🪴
25.) Explore Stunning Architecture Around The City
Tremendously tall to expansively wide, shining glass to dense stone, new modern marvels to century old symbols of Chicago achievement. Get lost in a sea of unparalleled buildings all expertly crafted down to the last detail. BUT fear not, there’s no need to search around the city for these towering titans, check out our list for all the best architecture spots!
Pro tip- Head to the Riverwalk near the DuSable Bridge for great views of the Wrigley Building, Tribune Tower, and the Marina Towers.
26.) A Chicago Cubs Game At Wrigely Field
Catching a Cubs game at Wrigley Field is one of the most fun things to do in Chicago and, without a doubt the most magical place in Chicago. A place where you can get a full feel for the city and everything Chicago is about. A place where the vibes and good times couldn’t be better. A place where you’re guaranteed to have a great experience whether the Cubs are in 1st place or last. A place like no other. A place that can only be found at a Cubs game at Wrigley Field.
Pro tip- Get bleacher seats for a fun, energetic party from the first pitch to the last. And check out our full guide to Wrigley Field for everything you need to know to have a great time! (Coming Soon)
27.) Walk The Beautiful Chicago Riverwalk At Sunset
The Riverwalk is the best of Chicago, and at sunset it gets even better. Walking along the smooth river as the setting sun glistens off of skyscrapers, sampling open restaurants and bars that line the walkways, or enjoying street performers posted on bridges above the water. When you’re at the Chicago Riverwalk at sunset, it feels like you’re walking through the heart and soul of Chicago.
28.) Institute for the Study of Ancient Cultures Museum
While the ISACM may sound like a long and boring name, the exhibits inside are anything but. See thousands of artifacts spanning well over a millennia of human history all the way back to the first civilizations of mankind. From colossal statues of ancient Egypt to tiny intricate works of art from ancient Mesopotamia. Plus it’s free!
Pro tip- The other galleries and attractions found on the University of Chicago campus are also well worth a stop.
29.) Field Museum
First opened in 1894, the Chicago Field Museum has been captivating people from around the world with its thousands of exciting exhibits. Found sandwiched between the Shedd Aquarium and Soldier Field, The Field Museum is a place where you can let your imagination wander as you roam the giant halls of this extensive collection. Explore the remains of prehistoric beasts and eras of ancient human history as you learn in amazement.
Pro tip- This spot is part of the Chicago CityPASS if you’re looking to save some money. 
30.) The Art Institue Of Chicago
Chicago is a city of gorgeous artistic expression, and the Art Institute of Chicago is at the heart of it all. Showcasing a vast collection of masterstroke paintings and finely crafted ancient sculptures, this museum is home to some of the most iconic works of art in the world. From Van Gogh to Monet, American Gothic to The Great Wave off Kanagawa, when it comes to The Art Institute of Chicago, you’re guaranteed to find works even the most novice of art enthusiasts will recognize and enjoy. You can even stand at “A Sunday on La Grande Jatte” and contemplate your day off…
Pro tip- Try to get there when they open at 11, as it can get pretty crowded pretty quickly.
31.) Chicago Architecture Boat Tour
When thinking of the best things to do in Chicago, an architecture tour probably isn’t one of the first things that come to mind. But this is much more than just an architecture tour. Gently floating down the Chicago River, you are taken on a journey through Chicago from the city’s construction centuries ago to the glamorous modern age. After you experience the soul of the city in a whole new light, it’s easy to see why the architecture boat tour is one of the best and most fun things to do in Chicago!
Pro tip- Don’t forget your camera as the boat tour offers fantastic shots of the city you can’t get anywhere else. 📸
32.) Starved Rock State Park
Just a short drive outside the city, this state park is a great, green outdoor escape from the city streets. Plenty of hiking trails through the forest to calm waterfalls or following alongside the wide Illinois river. If you’re looking for a break from the city life, this is the place to go.
Pro tip- LaSalle Canyon and St. Louis Canyon are 2 cool waterfall spots well worth checking out!
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