The Top Things to Do in Chicago, Illinois

The Windy City offers something for everyone, from outstanding live shows and renowned museums to waterside strolls and deep-dish pizza
The Windy City offers something for everyone, from outstanding live shows and renowned museums to waterside strolls and deep-dish pizza | © Ian Dagnall / Alamy Stock Photo
Photo of Molly Sprayregen
16 October 2020

As the third most populous city in the United States, Chicago is filled with people who are looking to have a good time. The Windy City offers something for everyone, from outstanding live shows and renowned museums to greasy, delicious pizza. These are the top things to do in Chicago.

Watch a live comedy show at one of Chicago’s famous venues

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Second City Theater, am improvisational comedy club in Chicago's Old Town neighborhood. Chicago, Illinois, USA.
© Bruce Leighty / Alamy Stock Photo
Chicago is world-famous for its comedy. The seemingly endless list of legends who got their start performing at the city’s many theaters includes Tina Fey, Stephen Colbert and Aidy Bryant. If you stop by a comedy institution, you may well see a performance featuring the next star of Saturday Night Live. The Second City is Chicago’s most famous comedy club, but the smaller clubs are equally, if not more, entertaining and are also significantly cheaper. Venues like IO and the Annoyance Theatre often have dozens of shows playing at once and offer more intimate settings.

Bike, run or walk the lakefront path

Hiking Trail
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ILLINOIS Chicago Runners and bicyclists use paved path among trees along lakefront on summer morning skyline in distance
© Kim Karpeles / Alamy Stock Photo

Chicago’s 18-mile (29km) lakefront path spans the entire east side of the city. It’s a picturesque place to spend a sunny day walking, biking or running beside beautiful Lake Michigan while also seeing gorgeous views of the Chicago skyline. Along the way, you’ll pass dozens of free parks and public beaches where you can take a rest, play some catch or go for a swim. The path recently underwent a massive expansion. Now, bikers and pedestrians use separate lanes, making it safer and more enjoyable for everyone.

Catch a professional sports game

Sports Center, Stadium
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Chicago Bulls basketball game at the United Center
© Danita Delimont / Alamy Stock Photo

No matter what season you find yourself in Chicago, there is bound to be a professional sports game to see. Chicagoans love their Blackhawks, Bulls, Bears, Cubs and White Sox, and even the frigid winter temperatures won’t stop them from getting out and supporting their teams. If you dare, bundle up for a mid-winter Bears game at Soldier Field, or wait for the sun to come out to enjoy a baseball game at Wrigley Field or Guaranteed Rate Stadium. You can also leave the weather out of the equation and watch the Bulls or Blackhawks play indoors at the United Center.

Take the Chicago Architecture Center’s river cruise

Architectural Landmark
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Tourists on an architectural boat tour in Chicago, Illinois
© Eric Murphy / Alamy Stock Photo

Hop aboard this boat cruise and spend time winding down the Chicago River while learning stories behind the fascinating architecture you see along the way. Chicago’s architecture is truly one-of-a-kind, and this fascinating tour is beloved by locals and tourists alike. If you’re interested in taking a cruise but architecture isn’t your thing, try a cocktail cruise or a sunset cruise, or one with live music. This city is interesting whether you see it late at night or early in the morning.

Grab a slice of deep-dish pizza

Pizzeria, American, $$$
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No visit to Chicago would be complete without at least one slice of deep-dish pizza, though the best place to get it is up for debate. Lou Malnati’s, Giordano’s, Pizzeria Uno, and Pequod’s are all city favorites. No one knows officially who invented it – but it’s distinctively delicious and consists of a high-sided dough filled with cheese, tomato and toppings. If you’ve got time and room in your stomach, why not try all the varieties and decide the best one for yourself?

Watch the Air and Water Show

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The U.S. Navy Blue Angels flight demonstration squadron performs during rehearsal before the 2017 Chicago Air and Water Show above North Avenue Beach
© Jerry Lai / Alamy Stock Photo

Every August, millions of people gather for a weekend on Chicago’s lakefront to watch a fleet of military jets flip and spin through the air. The show, which is completely free, can be seen for miles along the shoreline, but is best viewed from a boat, rooftop or beach. Pack a picnic to take with you, or take the opportunity to try a Chicago hot dog, made with beef and a large selection of distinctive toppings.

Explore the Riverwalk

Park, Architectural Landmark
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Looking down onto the Riverwalk in downtown Chicago on a warm summer day.
© D Guest Smith / Alamy Stock Photo

Along the most central part of the Chicago River, running right through downtown, is a pedestrian walkway stretching just over a mile (1.6km). It’s a lovely place for a stroll and offers a taste of nature in the city. There are any number of attractive waterside restaurants and bars to drop into while you’re there, or you could try renting a kayak to see the river from a different perspective. There are also lots of areas to simply sit back, relax and watch the boats drift by.

Experience Chicago’s best museums with CityPass

Museum, Aquarium, Building
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Chicago has so many amazing museums to choose from, and, with CityPass, you don’t have to pick just one. Instead, you can spend $108 (£83) per person, or $89 (£68) for children, to have access to five of them. Easy to use and great value, it’s not something to miss. With one CityPass, you can visit the Shedd Aquarium, the Willis Tower Skydeck, the Field Museum of Natural History, the Adler Planetarium or the Art Institute and the Museum of Science and Industry or the John Hancock Center Observation Deck.

Explore Chicago’s neighborhoods

Architectural Landmark
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Belle Shore Apartment Hotel in Bryn Mawr Historic District in the Edgewater neighborhood Chicago, Illinois, USA
© Richard Ellis / Alamy Stock Photo

Chicago is so much more than its downtown area. Its many neighborhoods are full of culture and wonderful things to do. Spend an afternoon enjoying Pilsen’s National Museum of Mexican Art, shopping local in quiet, pleasant Andersonville or wandering Edgewater’s Bryn Mawr Historic District. You can also head to the Old Town for more things to do, including famous beer pubs, shops selling artisanal fudge and spices and a wonderful old-time feel as you stroll around the neighborhood taking everything in.

Listen to live music

Music Venue
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Hot Chip at the Vic Theatre Chicago IL
© Heather Ahrens / Alamy Stock Photo

There is live music available all over this city. During your visit, find out what’s playing at some of the city’s best local venues, such as the Vic Theatre and the Aragon Ballroom. For dinner and a show, try Andy’s Jazz Club or Schuba’s Tavern. In the summertime, Millennium Park offers a free, outdoor weekly concert series. And if you’re willing to spend some money, a concert at Wrigley Field is an unforgettable experience – names including Paul McCartney, Jimmy Buffett and Elton John have played there.

Check out the Art Institute of Chicago

Museum, Art Gallery
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The Art Institute of Chicago Modern Wing on Monroe Street in Chicago USA
© Richard Ellis / Alamy Stock Photo
A literal Chicago institution, any culture fan shouldn’t leave the city without taking a gander at the 300,000 artworks housed here. Filled with masterpieces from every era imaginable, from Andy Warhol’s print of Elizabeth Taylor to Georges Seurat’s painting A Sunday on the Island of the La Grande Jatte. As if that wasn’t enough, there’s also a medieval armory. This impressive collection of suits of armor, swords and crossbows is found just past the Renaissance section of the museum. Truly, there’s something here for all tastes.

Experience an old-school movie theater

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Chicago really knows how to entertain its visitors. The Logan Theatre has been churning out fantastic evenings since it opened in 1929, and it’s still going strong. But don’t expect to see the latest Hollywood blockbuster every visit; you can see something a little different here. From renowned arthouse classics to the latest documentaries, you definitely won’t be falling asleep in the back row. Even the design and interiors are eye-catching – this is how cinemas were meant to be. The cherry on the cake is that it tops its popcorn with real butter.

Additional reporting by Alice Johnston.

These recommendations were updated on October 16, 2020 to keep your travel plans fresh.

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