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Visiting Chicago for the First Time? Here's What To See and Do

From Wrigley Field to food tours, here are our top recommendations for making the most of your first trip to Chicago.

A visitor checks out The Bean in Chicago
Hi, I'm Liam!

Liam Greenwell is a writer and teacher based in Mexico City. He is originally from Cambridge, Massachusetts. You can read more of his work at liamgreenwell.com and find him on Twitter @liam_greenwell.

Many know Chicago for Al Capone, deep-dish pizza, and the notoriously cold wind that comes off Lake Michigan. But there’s a lot more to this great American city, which is full of diverse neighborhoods, ranging from hipster hotspot Logan Square to the historic hub of Black culture in Bronzeville. You can admire incredible architecture, enjoy eclectic events and art, and eat foods from around the world, thanks to the many diverse communities that call this city home. Here are some great ways to enjoy your first visit.

1. Visit the Art Institute

Visitors view a painting at The Art Institute of Chicago.
The Art Institute of Chicago has one of the best art collections on planet.Foto: blvdone / Shutterstock

Admire world-class masterpieces.

One could make the argument that the Art Institute of Chicago has one of the greatest collections of art on the planet. From works by Vincent Van Gogh and Georgia O’Keefe to artifacts from across the ancient world, this museum’s collection would take days to explore completely. Start your morning in the Impressionist wing before it fills up with tourists to see Van Gogh’s colors up close, then join a guided tour that will give you a deeper understanding of the history and significance of the collection.

2. Cheer on the Cubs at Wrigley Field

Visitors enter Wrigley Field, the second-oldest ballpark in the country.
Wrigley Field is the second-oldest ballpark in the country.Foto: Felix Lipov / Shutterstock

Join the local crowd.

Wrigley Field is the second-oldest ballpark in the country still in use and one of the most atmospheric. The crowd is rowdy, the stadium historic, and the baseball itself gets better and better every year thanks to the rising fortunes of the Cubs. You can take home a blue and red cap as a souvenir, and when you’re done with the Cubs, you can hop on a brewery tour around the adjacent neighborhood of Wrigleyville. Alternatively, head south to see the White Sox at Guaranteed Rate Field.

3. Take a river architecture cruise

A cruise travels through the Chicago river.
Go on a Chicago River cruise and take in skyscraper views.Foto: f11photo / Shutterstock

Look up and learn.

Chicago boasts a plethora of fascinating buildings from the famous corn cob-shaped Marina City towers to Modernist, Art-Deco, and Neo-Classical masterpieces. On a Chicago River cruise, you’ll learn about the most significant spots with the help of a local expert while enjoying the unique look of the city’s skyline. Tours take you along all three branches of the river, and there’s even a full bar available onboard to help you enjoy the moment.

4. Visit one of the city's lesser-known museums

National Museum of Mexican Art in Chicago, Illinois.
The National Museum of Mexican Art always has fun exhibits.Foto: Prakash R / Triapdvisor

Learn about often overlooked aspects of Chicago culture.

Chicago may be all about the iconic sites and big-hitter attractions, but there are some off-the-beaten-path museums you'll want to check out while you're in town too. Take the National Museum of Mexican Art in Pilsen, where you can spot photographs by Graciela Iturbide and work by Chicano artists. Then there's the Ukrainian National Museum, which pays homage to Chicago's large Ukrainian community through historical and folk art exhibits, among others.

5. Sample some of the city’s standout grub

Diners eat a deep-dish pizza in Chicago.
Try some tasty deep-dish pizza in Chicago.Foto: ViihMTP / Shutterstock

Indulge in classics and haute cuisine.

There’s a reason people think of Chicago as a foodie city: it’s home to Fulton Market, world-class restaurants like the Michelin-starred Alinea, and chefs from a variety of cultures. To sample the city’s classics—including deep-dish pizza, hot beef sandwiches, and generously-topped hot dogs—book a tour that will take you to many of the iconic spots. You can even sample beguilingly weird Malört liquor, an iconic Chicago drink full of bitter botanicals.

6. Laugh (and cringe) at Second City

Actors during an improv show at Second City, a world-renowned improv theater, in Chicago.
Catch an improv show at Second City.Foto: Sean Pavone / Shutterstock

Spend an evening at an iconic comedy mecca.

Second City is a world-renowned improv theater that has nurtured some of the greatest American comics of the past few decades, from Bill Murray to Tina Fey to John Belushi. They provide a full program nearly every day of the week, and shows feature both up-and-coming stars and various stand-up greats. If you’re feeling inspired at the end of the evening, you can even sign up for online classes and keep your connection to Chicago going after your trip ends.

7. Explore Hyde Park

Exterior of the University of Chicago.
Take a campus tour of the University of Chicago.Foto: Damian Koziel / Shutterstock

Enjoy a neighborhood full of history and culture.

Home to the University of Chicago, Hyde Park is a historic and exciting neighborhood with a variety of museums and outdoor spaces and a regular calendar of cultural events. Because it’s on the South Side, it can also be a jumping-off point for exploring the city’s African American history. Start at the DuSable Black History Museum and Education Center, then take a walk to Promontory Point to watch the waves of Lake Michigan. Or join a tour of the South Side that includes a number of local highlights, including the house President Barack Obama lived in when he was a senator.

8. Imagine your dream home

A walker goes by Robie House in Chicago.
The Robie House was designed by Frank Lloyd Wright.Foto: James Kirkikis / Shutterstock

See the work of an American pioneer.

Frank Lloyd Wright remains one of the most influential American architects to ever live. He was a Midwesterner through and through, and his prairie-style houses were inspired by the region’s landscapes. Visit the Robie House in Hyde Park, then travel a bit west of the city to the suburb of Oak Park to see the artist’s home and studio. If you have enough time, consider joining a private tour that includes visits to 25 different houses in Oak Park that were designed or influenced by Wright.

9. Flex your green thumbs at Garfield Park Conservatory

A sculpture inside Garfield Park Conservatory in Chicago.
Garfield Park Conservatory is a massive 100-year-old greenhouse.Foto: Thomas Barrat / Shutterstock

Surround yourself with lush greenery.

Beloved by locals, Garfield Park Conservatory is a massive, 100-year-old greenhouse complex filled with rare plants from around the world. There’s no better place to get lost among cycads, ferns, and cacti. Easily accessible by subway, the conservatory also hosts events like yoga classes and movie nights. An afternoon here will make you feel you’ve stepped out of the Midwest and into Jurassic World.

10. Take a taco crawl through Pilsen

Tacos on a plate in Chicago.
Taste some yummy Mexican food in Pilsen.Foto: Antwon McMullen / Shutterstock

Have your dinner with a side of local culture.

Pilsen is the spiritual home of Chicago’s Mexican community, one of the largest in the United States. The best way to explore it? Through tacos, of course. Start at Carnitas Uruapan, a mom-and-pop store that has been serving hungry locals for decades. If you’re still hungry, head to Taqueria El Milagro for tacos or a burrito, or stop off at La Michoacana for ice cream, popsicles, or horchata. Once you’re full, check out Pilsen Community Books, then cap off the night at Punch House, where they’ll fill a literal fishbowl with the tipple of your choice.

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