The 14 Best Things to Do in Chicago (and Top Things to Avoid)

If visitors are tight on time, I always recommend a narrated river-boat architecture tour because who doesn’t love being out on the water? Wendella Tours & Cruises’ 45-minute and 90-minute sailings operate year-round along the Chicago River in downtown Chicago. It’s the best way to tick off a number of boxes, even if your time in Chicago is short, like 24 hours short. Gazing up at these skyscrapers from the water is an experience like none other. Ferris Bueller did it, and you should, too. Can’t get on a boat? Stand on the DuSable Bridge, above the Chicago River, where it meets Michigan Avenue.

I’d taken many class field trips to the Art Institute of Chicago before I realized, duh, this is a major art museum. All of a sudden, every other U.S. city I visited, except for a few, dulled in comparison. Even if there isn’t a traveling show, the museum’s permanent collection is impressive, including more recent acquisitions now on display in the 264,000-square-foot Renzo Piano-designed Modern Wing, featuring works by René Magritte, Pablo Picasso, Henri Matisse, and others. Another source of pride is the world’s second-largest collection of Claude Monet paintings outside of France, clocking in at 33 works, including from the French Impressionist artist’s “Waterlilies” and “Haystacks” series.

This 24.5-acre park debuted in 2004 and, like many, I immediately fell in love with “The Bean” and Crown Fountain. However, it took a friend with kids to take me past the park’s Frank Gehry-designed Pritzker Pavilion, where I’ve sat and listened to free jazz and Chicago Symphony Orchestra concerts during the summer months and into a 20-acre playground that’s—wait for it—ideal for adults, too. Here we were at Maggie Daley Park (open since 2014), fully grown adults, zipping down covered slides and howling with laughter. It’s also a neat family-friendly place. This is easy to find if you know where to look: just take the pedestrian bridge on the far eastern side of Millennium Park.

I’m that person rolling my eyes a split second before smiling for a selfie at “The Bean,” the shiny, stainless-steel and bean-shaped—hence its moniker—sculpture by British artist Anish Kapoor at the entrance to Millennium Park. The sculpture’s real name is “Cloud Gate” but nobody calls it that. The thing is, this is a rite of passage for any tourist, a way to declare to people, ”Yes, I visited Chicago.“ Because if you haven’t taken your photo in front of the Bean, you can’t join that club of people who have marveled at seeing a very dimensional view of themselves.

If your friends are tired of you sending them clips from Saturday Night Live, then check out Second City, which is an incubator for a lot of the cast, including Dan Akroyd, Amy Poehler, Jason Sudeikis, and Cecily Strong, before they head to the Big Apple. I took way too long to get there, thinking it would be cheesy as heck, and now regret that delay because never have I laughed that hard in one night. While it’s also in Toronto and New York City, the Chicago location came first, in 1959. If you happen to be in town on a Tuesday night, the Ten Dollar weekly series is a bargain, costing only $10.

When it comes to botanical gardens, Chicago Botanic Garden gets the most attention, but it’s not even in Chicago. It’s an hour’s drive north of downtown Chicago, in the North Shore community of Glencoe, in Cook County. (Although, yes, the light show—called Lightscape—taking place each winter is amazing and a difficult ticket to snag.) But back to Garfield Park Conservatory. Head here instead. Located in Chicago’s Garfield Park, miles west of downtown Chicago, it’s quietly been here since 1908 and has hosted world-class shows that connect flowers and plants with art, including works by Alfred Ramos Martinez and Dale Chihuly.

While Chicago’s known for hosting Broadway musicals and other live theater at the Steppenwolf and the Goodman, this experimental theater is a fun sidestep. The Infinite Wrench might sound like a tongue twister, but trust me, your jaw is going to drop hard when you see this play by the Neo-Futurists, a troupe that dates back to 1988 and inspired offshoots in London, San Francisco, and New York City. It’s a series of 30 plays performed in 60 minutes, and kicks off Fridays and Saturdays at 10:30 p.m. (ideal for night owls) and Sundays at 7 p.m.

The country of Ukraine needs our support right now, and so do Ukrainian-Americans, many of whom reside in this near-West neighborhood that got its official name in 1983, but has attracted Ukrainians since the 1880s. This summer, the neighborhood earned a distinction as an Illinois state-designated cultural district. Learn more about their culture at the Ukrainian National Museum of Chicago and Ukrainian Institute of Modern Art, or sample their cuisine at Tryzub Ukrainian Kitchen, Old Lviv, or Anelya. Pick up gifts imported from Ukraine at Delta M, which has the cool distinction of being the country’s oldest and largest Ukrainian-goods store, dating back to 1960. In recent years, this neighborhood has also unleashed a lot of Airbnbs rentals, allowing for a more immersive stay.

I am *still* in shock, people, that the Cubs won the World Series in 2016 after traveling to Wrigley Field on Chicago’s North Side for dozens of games as a little tyke and watching them lose, lose, lose. What makes this ballpark stand apart is its age: it’s now 111 years old, making it the second-oldest in the U.S. (Fenway Park in Boston is two years older.) If your visit doesn’t coincide with a game, you can always take a guided 90-minute tour on a non-game day, although there are abbreviated tours on game days, too. Concerts are hosted here on occasion, too, with recent acts that have included Pearl Jam and—in one evening—Def Leppard, Journey, and Steve Miller.

While we’re still waiting for the doors to open at the Barack Obama Presidential Library (the latest news is to expect spring of 2026), we know it’s going to be in Jackson Park, on Chicago’s South Side. Immediately west of the park is Hyde Park, a neighborhood that’s home to other gems, like the University of Chicago, the Frank Lloyd Wright-designed Frederick C. Robie House (offers tours), and indie bookstores like Powell’s Books Chicago (Portland’s Midwestern sibling). Cap off a day of exploring with dinner at Virtue, where chef-owner Erick Williams nabbed the title of Best Chef: Great Lakes by the James Beard Awards in 2022.

One of Chicago’s best treasures is its lakefront and, no, this is not a small lake. Lake Michigan is one of five Great Lakes and a haven for boaters as well as lake lovers who just want to recreate alongside it. From East 71st Street on the South Side to Kathy Osterman Beach in Edgewater, on Chicago’s North Side, the 18-mile-long lakefront trail is paved and open to bicyclists, dog walkers, day hikers, and roller-bladers. Public restrooms are located along the way and, of course, you don’t have to hike the whole trail, but maybe you want to? Even if you have just an hour to stroll, it’s a great way to experience the city.

I’m not so hot on attractions that include vertical heights, and I’ve already been up Willis Tower, back when it was still called Sears Tower, but I’m already plotting a return. That’s because you can now enjoy deep-dish Giordano’s pizza at Willis Tower’s Skydeck Chicago, America’s tallest observation deck, with The Ledge, a glass-enclosed suspended deck on the 103rd floor, a popular bucket-list item (though not for me). I’m thinking that layers of cheese atop a buttery crust will be the perfect distraction to facing my fears. Before your visit, peruse the dates available and try to lock in a reservation. This is not a walk-in experience.

Even if science wasn’t your favorite subject in school, this museum is so vast and goes deep in so many topics that everyone can find something to like. Even its Palace of Fine Arts building is cool as it was built for the 1893 World’s Columbian Exposition, hosted in Chicago. (Side note: if you’re scratching your head at the museum name, in 2024, the former Museum of Science and Industry’s name was tweaked to include the name of a local benefactor.) One exhibit is all about Spider-Man, while another talks about the tragedy of ocean plastics.  During the summer, the museum stays open later on Sundays, adding some flexibility for travelers.

Because this 1916 pier was only rebuilt in 1995, long-time Chicagoans forget about this tourist trap on the edge of downtown, where it meets Lake Michigan, and where you’d better be ready to elbow your way through chain restaurants, souvenir shops, and other glitzy stuff to get to the goods: among the best waterfront views in Chicago. If you still want to go, have a definite plan: I recommend pushing past all the tourists and visiting Offshore Rooftop, the world’s largest rooftop bar, on a weeknight and ordering a cocktail as you gaze out at the water.

Please don’t visit Chicago during winter unless you absolutely have to. It can dip below zero or be as “high” as in the 30s Fahrenheit. But the real issue is the wind chill. It’s the Northern cousin to the South’s humidity. It’s going to ice you out. I have gotten into literal discussions—er, arguments, because I know I’m right about this—with others about whether or not Chicago tops New York City for its frigid winters. But don’t just believe me. There’s a reason you can find a hotel in the Loop for under $135 a night during January and February. Fine, do it. But you probably won’t leave the hotel. And what kind of vacation is that?

This is an Irish town, yes, but that doesn’t mean you need to ooh and aah at the Chicago River dyed green in honor of St. Patrick’s Day, the national holiday commemorating Saint Patrick, Ireland’s beloved saint. Drum up some photos in your social-media feed instead, from the comfort of your couch, and come to Chicago any other day of the year. Just not the closest Saturday to St. Patrick’s Day. There are lots of Irish bars and pubs throughout Chicago that will happily serve you a Guinness day and night. The crowds in downtown Chicago, for both the parade and bar crawls, just aren’t worth it.

It’s hard to find a restaurant, in any city, that checks all the boxes—amazing food, fun scene, great view, all-day dining, and a decent cocktail/wine/beer list. Cindy’s Rooftop, perched on the 13th floor of the Chicago Athletic Association hotel, does all that. As of last year, there’s another reason to visit: its former chef, Kaleena Bliss, competed on Top Chef’s 21st season. Take the elevator to the top floor, where a seat under the glass indoor atrium and overlooking Millennium Park (year-round there are fire pits on the patio to keep things cozy) is a nice spot to chill. On the menu, which serves daily lunch and dinner, and weekend brunch, are delicacies like oysters and caviar, alongside burgers, deviled eggs, and pasta, as well as farm-fresh cocktails like the bourbon-infused Chi Shandy Shake.

Even though it’s been open since 2017, this 11-room hotel often falls under the radar, which is really too bad, as I love a hotel that 100% takes on a theme. In this case, it’s publishing, in ode to the Free Methodist Publishing House that once worked out of this building. With hardwood floors, gallery walls, and plush furnishings, this feels more like a friend’s cool loft than an impersonal hotel, and you can also hang out in front of the fireplace in the Great Room. All rates include a hot, complimentary breakfast, and The Press Room (a wine bar) is under the same roof. The location is equally coveted: West Loop is adjacent to Fulton Market, where all the trendy restaurants are, in this city’s former meat-packing district.

I’ve had so many “bests” at The St. Regis Chicago, such as the best facial of my life, a Japanese breakfast that reminded me of my time in Japan, and a killer view of Chicago at night. This hotel opened in 2023 in the new-ish neighborhood of Streeterville (essentially just north of Millennium Park and just south of Navy Pier) and is in a high-rise designed by the city’s own Jeanne Gang, which makes this the tallest building designed by a woman. There are two restaurants—Miru and Tre Dita—as well as a spa, indoor pool, and fun retail pop-ups in the lobby, such as a candy cart, flower cart, and gifts during the holidays. Each evening, the lobby hosts a free Champagne reception complete with a sabering ritual to uncork a bottle with flair. The rooms are among Chicago’s largest and don’t skimp on any swank.

Even if you’re not seasoned with public transportation, give Chicago’s “L” (short for the Chicago Transit Authority’s elevated rail system) a try. I hate taking the underground subway when I travel to other cities, including New York City, because I didn’t travel all that way to be shot through dark tunnels at breakneck speed. I want to see things. Take notes on what to come back to. Another fun way to get around on a nice day is by renting a Divvy bike. This is Chicago’s bicycle-share program, and you can find kiosks all over the city. And if you’re feeling tired, there are e-bikes, too.