As the third largest city in the US, Chicago boasts a thriving arts scene, fantastic food, and a wide variety of museums and attractions. There’s something for everyone in this eclectic and historic city.
As a Chicago native who moved away long ago, I still yearn for the city’s bustling streets, iconic treats, and fun happenings.
Here are the best things to do in Chicago, from a native who misses it.
The Art Institute of Chicago
The Art Institute of Chicago tops many lists of things to do in the iconic city for a good reason. It’s one of the top art museums in the country and is filled with pieces from antiquity to modern art.
Stroll through the medieval wing to see the artistry of armor and weaponry from the Middle Ages, then pop up to the impressionism section to view an impressive array of Monet’s haystacks. The museum features hundreds of famous artworks from the most renowned painters in all of history.
The Field Museum of Natural History
Visit Sue, the largest, most intact tyrannosaurus rex fossil ever discovered, at the Field Museum of Natural History. Discovered by Sue Hendrickson in South Dakota, this impressive specimen greets guests in the Griffin Hall evolution exhibit.
The Field also features a massive collection of Egyptian antiquities, a taxidermy nature walk, an exhibit on the biology of plants and animals, and much more.
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The Shedd Aquarium
The Shedd Aquarium and Oceanarium holds three million gallons of seawater, displaying six diverse habitats. Visit a Caribbean reef, the icy waters of polar oceans, and the creatures lurking in the deep.
Don’t forget to visit the Oceanarium complex, home to white-sided dolphins, beluga whales, and the always-entertaining sea otters.
The Museum of Science and Industry
Do you want to see a real German U-boat from World War II? The Museum of Science and Industry in Chicago is one of the only places you can see one in the country.
That’s not all. The impressive museum also features a flight simulator, a coal mine exhibition, a fairy tale castle, and numerous special exhibits throughout the year.
The Chicago History Museum
Delve into the Second City’s unique history by exploring the Chicago History Museum. The gallery showcases America’s story, emphasizing Chicago’s central role.
Discover Chicago’s growth as a multicultural community, learn about Martin Luther King Jr’s time in the city fighting for civil rights, and review the women’s protests and fight for suffrage. The museum highlights the city as America’s crossroads, and it’s one of the best things to do in Chicago for history buffs.
The Adler Planetarium
Become an astronomer for a day with a visit to the Adler Planetarium and set your sights on the skies! The Adler Planetarium boasts a unique sky dome theater, where they offer numerous presentations on constellations, the solar system, and the universe throughout the day.
It’s also home to the largest public telescope in the Chicagoland area and numerous exhibits about space, including a space visualization lab, a gallery where visitors can learn about our solar system, and a program highlighting ancient civilizations’ obsession with the skies.
See an Iconic Team Play
Chicago is home to some of the most iconic teams in sports history. Mike Ditka’s 1985 Chicago Bears, Michael Jordan’s elite Chicago Bulls, and the loveable loser (until 2016!) Chicago Cubs.
Although the players change, the teams remain symbols of the magnificent city. Chicago’s Soldier Field is one of the most historic football stadiums in the country. The United Center hosts the Bulls and the Blackhawks and features the iconic Michael Jordan statue. Wrigley Field on the North Side is on every baseball fan’s bucket list.
While in the city, you should also check out the White Socks down at US Cellular Field and the Chicago Fire, the soccer team that also plays at Soldier Field.
View the City from Above
Chicago features one of the best skylines in the nation. The industrial city ranks 11th for the most completed skyscrapers, over 150 meters worldwide. The only American city ranking higher is New York.
One of the top things to do in Chicago is view the majestic skyline from above. Head to the building formerly known as the Sears Tower, which was renamed Willis Tower, to the chagrin of many residents, and visit the Skydeck to view the city from 1300 feet in the air. At one time, the Sears Tower was the tallest building in the world, but it’s long since lost the title.
If you’d rather view the skyline while enjoying expensive drinks, head to the Signature Room on the 97th floor of the John Hancock building.
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Take an Architectural Tour on the Chicago River
Chicago is renowned for its impressive architecture. One of the best ways to explore the majestic buildings is by water.
Take a boat ride down the Chicago river and out towards Lake Michigan to discover the history of Chicago’s most notable buildings, learning about their development and the fascinating stories behind them.
Explore the History of Al Capone
Chicago was home to one of the United State’s most notorious criminals, the 1920s gangster Al Capone. The city celebrates its nefarious history with various tours showcasing Capone’s haunts.
Take a Chicago Crime Tour to learn true stories about Capone, John Dillinger, and the Untouchables, or opt for the ghosts and gangsters tour for a spooky look at Chicago’s infamous past.
Try a Chicago Deep Dish Style Pizza…
Chicago is known for the pizza pie, a deep dish delicacy dripping with cheese and stuffed with your favorite pizza toppings.
The debate over which pizzeria serves the best Chicago deep dish rages on, but you won’t be disappointed with Lou Malnati’s or Giordano’s.
Then Eat REAL Chicago Pizza
Native Chicagoans rarely eat deep-dish pizza. Though the famous pie was born in the city, most locals prefer Chicago tavern-style pizza, a chewy thin-crust pizza loaded with toppings and cut into manageable squares.
Head to Beggar’s Pizza, Aurelio’s, or Vito & Nick’s for the best pizza you will ever have in your life.
Have an Italian Beef Sandwich
Chicago may be known for its pizza and hotdogs, but visitors would miss out if they didn’t try an authentic Italian beef sandwich while in the city. The delicious sandwich features roast beef cooked in au jus, served on deliciously baked Italian bread with your choice of cheese and peppers. Depending on how soggy you want the bread, you can get it dry, wet, or dipped.
For the best beef sandwich, try one of the many Portillos locations scattered throughout the city or visit the iconic Al’s Beef.
The bustling Chinatown region on Cermak Rd features restaurants and shops celebrating Chinese culture.
Dine at the Moon Palace Restaurant for the best spring rolls and hot & sour soup you’ve ever tasted, and stroll through the corridor to explore the small family-owned shops on the main strip.
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Ride the Ferris Wheel
The iconic ride debuted at the Chicago World Fair in 1893, so it’s only fitting that the city would build a giant version at a popular tourist destination.
The Centennial Wheel sits atop Navy Pier and takes passengers 200 feet into the air to view the marvelous lakeshore. The gondolas are enclosed and climate controlled so guests can enjoy the ride even during the bitter cold of a Chicago winter.
Visit a World Class Zoo
Chicago is home to two beautiful zoos, Brookfield Zoo in the near west suburbs and Lincoln Park Zoo in the city. Lincoln Park Zoo is free and one of the best things to do in Chicago on a tight budget.
Brookfield Zoo isn’t free, but it’s the better zoo. It has a massive primate exhibit featuring gorillas and an impressive reptile house. The Big Cat Walk is home to Brutus and Titus, African lion brothers who delight visitors.
Explore the Diverse Neighborhoods
Visitors to Chicago should venture outside the main downtown loop to explore the diversity of neighborhoods thriving throughout the city.
Head to Taylor Street for an authentic Italian experience, or check out La Villita (the Little Village) for an incredible Mexican experience. Explore the differences between Lincoln Park and Wrigleyville while supporting the small local businesses flourishing in these areas.
Visit an Iconic Park
Visitors to Chicago will be delighted at the numerous public parks and green spaces scattered throughout the city.
The top two to visit are Grant Park, home to the majestic Buckingham Fountain, and Millennium Park, famous for the Cloud Gate sculpture, lovingly referred to as “the Bean.” The parks district hosts numerous events throughout the year, including live shows and festivals.
Check out the Live Music Scene
Chicago is known for its thriving music scene. The Smashing Pumpkins, Rise Against, Chicago, and many more fantastic rock bands hail from the city.
Head to one of Chicago’s most iconic theaters, such as the Aragon Ballroom or the Riviera Theater, to catch a band on the rise. In the 1990s, rock bands such as Green Day and the Foo Fighters were common sites at these mid-sized venues, though they now generally play larger arenas.
Check out the Metro near Wrigley if you’d rather see a local band just getting started.
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Experience Live Blues
Many cities can claim the title of “Home to the Blues.” Though the musical style wasn’t developed here, Chicago did help blues singers find their voice and propelled the Blues into popularity.
While in Chicago, celebrate its historical love of Blues by catching a live performance. Head to Blue Chicago on Clark or Buddy Guy’s Legends on Wabash to get in the groove with live Blues.
Enjoy Live Theater
As an artsy city and Cultural icon, Chicago hosts numerous theaters for enjoying a live play or musical. Head to the Shakespeare Theater to catch classic works by the literary master, or visit the Beverly Arts Center to see actors in training perform.
The downtown theater district holds an abundance of theaters featuring off-broadway plays, traveling shows, and local creations.
Head up to Six Flags
Are you looking for a thrill on your visit to Chicago? Head up to the Northern suburb of Gurnee to visit Six Flags Great America.
Ride the American Eagle, an iconic wooden roller coaster with a 147-foot drop, or opt for the wild loops of the Superman coaster. Six Flags Great America also has a wonderful children’s area with tons of rides for the little ones.
Bar Hop Down Rush Street
Chicago’s Rush Street is known for its impressive lineup of high-end bars and restaurants. Visit Gibson Steak House for a luxury meal, then wander down the street to check out the strip’s various independent bars and clubs.
If you’re looking for a classy night out on the town, you won’t want to miss this street!
Taste the Best of Chicago
Every year in July, Chicago hosts a massive Taste of Chicago festival in Grant Park. The festival brings the best of Chicago’s culinary flavors to one spot, allowing tourists to sample a wide array of local foods from the best restaurants.
The Taste of Chicago can get pricey, be sure to bring a full wallet along with an empty stomach.
Relax in a Massive Conservatory
Want to escape the hustle and bustle of the city and relax in a breathtaking greenhouse? Visit the Garfield Park Conservatory.
Described as “landscape art under glass,” the conservatory is home to two acres of indoor display and a lush outdoor garden. Explore desert botanicals, a fern house, and a tropical farm forest, and learn about the importance of botanic diversity during your visit.
Visit the Cultural Center
The Chicago Cultural Center is an impressive architectural landmark promoting the city’s arts. Built in the 1880s as a library, the center is still vital to Chicago’s thriving arts scene.
Visit the building to see the largest stained Tiffany dome, and stay to support one of the many events the center host in support of local artists.
Attend the Chicago Symphony Orchestra
The Chicago Symphony Orchestra is one of the best in the world. While visiting, grab tickets to see the world-class musicians perform impressive jazz sessions, classical symphonies, and pop culture hits.
The orchestra performs a variety of concert series, be sure to check their calendar to see what is offered during your visit.
Stroll Through an Outdoor Art Gallery
Visitors can’t miss the impressive sculptures and public murals scattered throughout the city. The Daley Plaza features a giant sculpture by famed artist Pablo Picasso, while the remarkable Flamingo greets guests at the Federal Plaza.
Numerous neighborhoods also feature public mural walls. Head to Pilsen on the South side for an outdoor gallery created by local artists, or keep on the lookout for Hebru Brantley’s Flyboy featured on murals in Uptown, Roosevelt Station, and near the McCormick Green Line Plaza.
Support Contemporary Art
Chicago’s Art’s district hosts nearly 30 artist-run galleries, making it the perfect place to score authentic artwork from contemporary artists. The area near 18th and Halsted features blocks of galleries and artist’s lofts and hosts an art walk for visitors on the second Friday of each month.
West Town is quickly turning into a gallery district as well. The neighborhood on Chicago Avenue started attracting artists and galleries in the past few years and now hosts a diverse group of local artists.
Catch a Comedy Show
Many great comedians got their start in Chicago, including Jim Belushi, Bernie Mac, and Bill Murray. While visiting, check out one of the many comedy clubs to see the newest group of young comedians perfect their art.
Check out the Laugh Factory, Second City, or Zanies to see stand-up comedy and improv groups performing nightly.
Take a Ride Along the Lake
Chicago’s Lake Shore Drive is an iconic stretch of road featuring the massive city to the west and one of the world’s largest lakes on the right.
It’s hard to take in the impressive views while driving, so instead, opt to rent a bike and ride along the Lakefront trail. The route takes you through Grant Park’s scenic waterfront, past Navy Pier, and all the way up to North Avenue Beach. The entire trail is 18 miles, which might be ambitious for casual riders, but it’s worth exploring in sections.
Shop Along the Magnificent Mile
The Magnificent Mile rivals Los Angeles’s Rodeo Drive for shopping connoisseurs. The mile-long stretch along Michigan Avenue includes over 400 retailers, including department stores, specialty shops, and boutiques.
The Magnificent Mile is within walking distance of many of the city’s best hotels and features numerous dining options and gourmet grocers.
Explore a Specialty Museum
Although renowned for the giant museums discussed above, Chicago is also home to numerous smaller niche museums.
Explore the Peggy Notebaert Nature Museum, the International Museum of Surgical Science, the American Writer’s Museum, or the numerous other specialty museums scattered throughout the city for an experience unique to Chicago.
The Best Time to Visit Chicago
The only limitation to visiting Chicago is the weather. Winters in Chicago can be brutally cold, and lake-effect snow often makes driving difficult.
The best time to visit Chicago is the late spring and early fall when temperatures are mild.
Summertime is also an excellent time to visit, primarily as the Taste of Chicago occurs in July. The only limitation to summer visits is the city can get hot and humid, but typically the temperature does not exceed 90 degrees.
Hundreds of Things to Do in Chicago
Chicago is an iconic city filled with museums, restaurants, theaters, galleries, and more. There’s something for everyone in America’s second city.
If you want to visit a fantastic city with tons of things to do, consider a trip to Chicago. You’ll fall in love with the city.
Melanie launched Partners in Fire in 2017 to document her quest for financial independence with a mix of finance, fun, and solving the world’s problems. She’s self educated in personal finance and passionate about fighting systematic problems that prevent others from achieving their own financial goals. She also loves travel, anthropology, gaming and her cats.