The 41 Best Ways to Pass the Time in Chicago (2024)

There’s a reason why Ferris Bueller’s Day Off set a dreamy, dialogue-less sequence inside this gorgeous art museum, which at one million square feet is one of the largest in the world. You could spend the better part of a day exploring its incredible collection, which spans thousands of years and includes famous works like Picasso’s "The Old Guitarist" and Seurat’s pointillist masterpiece "A Sunday Afternoon on the Island of La Grande Jatte."

Built in 1914, Chicago’s baseball stadium is nicknamed the “Friendly Confines” and offers tours of the field. Fans can hang out in the dugout and stand in the outfield, imagining what it was like when Babe Ruth pointed to the bleachers here during the 1932 World Series. The surrounding neighborhood of Wrigleyville is packed with bars and a rowdy place to spend time before or after games.

It’s every tourist’s favorite activity for a reason: There’s no more pleasurable way to get to know the city than by floating comfortably down the river, and no better way to learn about the birthplace of the skyscraper than to have an expert explain the Art Deco opera house, the corncob-like Marina City, or the Neo-Gothic Tribune Tower.

This distinctive black tower (you’d be forgiven for still calling the building by its former name, the Sears Tower) was the tallest in the world for the last 25 years of the 20th century, and visitors can step into glass boxes that jut off the building at its 103rd floor. On a clear day, a guest might glimpse beyond Illinois to views of Indiana, Michigan, and Wisconsin.

Since it was formally dedicated in 2006, artist Anish Kapoor’s giant, bean-like sculpture—which is comprised of stainless steel plates welded together and polished until seams became invisible—has become one of the popular stops in Chicago, particularly due to its location in the beautiful new Millennium Park. The reflective surface captures the clouds above and buildings nearby in a warped, dreamy way, and is a perfect place to grab a selfie.

Aside from Cloud Gate, the park has offered loads of attractions since its opening celebrated the turn of the millennium. A classical music series is free for ten weeks every summer, as is a movie series played on a 40’ LED screen. In the winter, ice skating (including lessons) is also available gratis.

The great Chicago Tribune restaurant critic Phil Vettel once confessed he is slow to award 4-star ratings, even in the famously exquisite local fine dining scene. He has granted only five—including to the legendary Alinea, which is also on this list—but in 2016 he added a sixth, a hidden gem west of the Loop called Oriole, named after the Baltimore Orioles baseball team by chef Noah Sandoval and his wife and business partner Cara, who appreciate all things Charm City. Since that rave, Oriole has continued to flourish, with a tasting menu (now $285) that has only ripened with time and three times the space, which is still likely not enough room to accommodate all those waiting for one of Chicago’s toughest reservations. Don’t take their word for it: Michelin awarded the restaurant a remarkable two stars.

Second City is the name of both the infamous improv comedy troupe and the theater in Chicago where they perform. The group has churned out many (if not most) of the most famous comedians of the last 50 years, including Saturday Night Live legends like Bill Murray, John Belushi, Chris Farley, Tina Fey, Amy Poehler, Kate McKinnon, and so many more, and there are shows seven nights a week.

Perhaps America’s most famous and influential architect, Frank Lloyd Wright designed the structure and interiors of this building now located on the University of Chicago’s campus. It is now widely considered the most cohesive example of his “Prairie” style and one of the most important buildings in the country, with its emphasis on the horizontal via dramatic cantilevered roof eaves and deceptively long, skinny bricks.

Along the western shore of Lake Michigan runs an 18-mile paved path that is perfect for jogging, cycling, rollerblading, or just taking in the incredible views of the lake. The path connects visitors to the city’s most popular beaches and parks, along with major attractions like the Lincoln Park Zoo or Navy Pier, and is dotted with waterfront restaurants.

Book nerds of all ages will enjoy this interactive space, where visitors can play with a timeline of the nation’s greatest writers and learn about their daily disciplines and best quotes. Recent temporary exhibits included the influence of immigrant writing in the U.S. and a look at Ray Bradbury’s legacy.

It’s not a coastal city but the endless expanse of Lake Michigan and its surprisingly turquoise waters could convince you otherwise. North Avenue Beach is typically the most popular (and be sure to grab a drink at Castaways), but you can hit Ohio St Beach to swim basically among the skyscrapers, or 57th St Beach if you’re into watersports.

This transformation of the northern end of Grant Park is dedicated to the former first lady of Chicago, who died from cancer in 2011, and inside, there’s a garden dedicated to cancer survivors. Elsewhere are state-of-the-art activities for kids of all ages, including slides galore, incredible climbing walls, and an ice-skating “ribbon” that curls around the area like a lazy river.

Chicago’s opera, which was founded in the 1950s, kicked off by welcoming Maria Callas for her American debut. It’s been welcoming audiences into the glory of the art ever since, making opera accessible to all with a training center for singers, community programming, and even by streaming previously recorded operas completely free. Plus, it’s worth attending just to soak in the stunning Art Deco theater space within the Civic Opera Building.

The Goose Island Beer Company is proud to call itself Chicago’s beer, and you can sip the 312 beer (named for the local area code) and more at their Fulton St Brewery and Tap Room. The Marz Community Brewing Company aims to be both a brewery and old-fashioned social club and area collective, and Metropolitan Brewing creates German-style lagers with a tasting room and patio right on the river.

Considered one of the best restaurants in the world since it opened in 2005, Alinea serves a many-coursed tasting menu that helped pioneer the art of molecular gastronomy. Guests have their minds blown and senses delighted by each gorgeously plated little work of art.

Often it’s the small museums focused on a particular time that teach the most, and this spot dedicated to the art and design of the Gilded Age could have that effect. Housed appropriately in an 1880s mansion nicknamed the “Marble Palace,” the museum contains loads of stained glass, Tiffany chandeliers, scrolling candelabra, and elaborately carved furniture.

Want to blast your tongue? Then try the wildly acidic foodstuff that is a Windy City frankfurter, which is a humble hot dog topped with pickled peppers, a pickle spear, sweet pickle relish, chopped onions, mustard, and whatever else the best shops can come up with. They’re available at any of the many hot dog stands set around the city.

Akin to New York’s Fifth Avenue and Rodeo Drive in Los Angeles is this strip of over 450 high-end shops, as well as hotels, restaurants, and famous skyscrapers running along Michigan Avenue. Visit during the holidays to enjoy the festive holiday windows, get your shopping in, or just stoll with kids to appreciate the towering, glittering trees set throughout the path.