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.

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 experience. 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.

Second City is a world-renowned improv theater that has nurtured some of the greatest American comics of the past few decades, from John Belushi and Bill Murray to Tina Fey. 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.

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. Save room to sample the city’s classics—including deep-dish pizza, hot beef sandwiches, and generously-topped hot dogs. Don't forget to try the beguilingly weird Malört liquor, an iconic Chicago drink full of bitter botanicals.

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 are Frank Lloyd Wright obsessed, there's a tour that includes visits to 25 different houses in Oak Park that were designed or influenced by Wright.

Wrigley Field is the second-oldest ballpark in the country, is still in use, and is one of the most atmospheric. The crowd is rowdy, the stadium historic, and the baseball itself gets better every year thanks to the rising fortunes of the Cubs. Take home a blue and red cap as a souvenir, and when you’re done with the Cubs, hop on a brewery tour around the adjacent neighborhood of Wrigleyville. Or, if you haven't had enough sports, head south to see the White Sox at Guaranteed Rate Field.

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.

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.

Home to the University of Chicago, Hyde Park is a historic neighborhood with a variety of museums and a 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 stop at the house President Barack Obama once lived in.

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.