40 Best Things to Do in Chicago, From Iconic Sites to Can't-miss Museums

Planning a trip to the Windy City? Here are 40 of the best things to do in Chicago.

Chicago may not be the city that never sleeps, but there is surely more to do here than you'll have time for. Whether it's world-class art, a cultural experience, or sports you seek, you'll find it in the Windy City. Here are 40 of the best things to do in Chicago.

See masterpieces at the Art Institute of Chicago.

This downtown museum isn't just an architectural gem, it's one of the best art museums in the United States. It's home to famous pieces, including Edward Hopper's "Nighthawks" and Grant Wood's "American Gothic," as well as the largest collection of works by Claude Monet outside of Paris.

Take an architecture river cruise.

With several buildings designed by greats like Frank Lloyd Wright and Ludwig Mies van der Rohe, Chicago is an architecture nerd's paradise. And one of the best ways to appreciate the cityscape is from the river. While there are dozens of cruise operators, Chicago's First Lady Cruises stands out for its 90-minute architecture cruise guided by experts from the Chicago Architecture Center.

Tour a submarine at the Museum of Science and Industry.

The largest science center in the Western Hemisphere. this Hyde Park museum is a great place to spend a cold or rainy day. The permanent exhibits focusing on science, technology, and nature are extensive but it's worth upgrading your ticket to include a tour of the only German submarine in the U.S. Check the schedule for special exhibitions, which can also be a treat.

Aerial view of downtown Chicago with city parks and the lake in view
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Step back in time at the Chicago History Museum.

Chicago is where Al Capone once played and where Playboy was born. It's a city full of stories to tell, and there's no better place to discover them than one of the city's oldest cultural institutions, the Chicago History Museum.

West Wacker Drive Skyline in Chicago
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Meet a dinosaur at the Field Museum of Natural History.

The Field Museum is one of the largest natural history museums in the world, and its permanent collection includes a number of fossils and the remains of Sue, the Tyrannosaurus Rex. Sue is estimated to be 67 million years old and made her debut at the museum in 2000.

Have a few laughs at a comedy club.

Several famous comedians (Tina Fey, Chris Farley, and Jim Belushi, to name a few) got their start at Chicago's well-known comedy clubs, including The Second City. New stages have since popped up, like Laugh Factory and The Revival. Who knows? You might see the next rising star of Saturday Night Live before they hit it big.

Listen to live music.

Chicago is a live music heaven, with venues that host performers of all genres throughout the year. In the mood for classical? Experience the talents of the Chicago Symphony Orchestra. Craving jazz? Head to the historic Green Mill jazz club. The city is also home to several music festivals, including Lollapalooza, Riot Fest, and world-famous blues and jazz festivals.

Aerial view of North Avenue Beach in Chicago, Illinois
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Go to the beach.

Believe it or not, Chicago is a beach town during the summer. Oak Street and North Avenue beaches are two sandy beaches along Lake Michigan that are close to downtown and will allow you to bask under both the sunshine and the shadows of the city's skyscrapers.

Brave the Skydeck of the Willis Tower.

Formerly known as the Sears Tower, this towering giant was once the world's largest skyscraper. That may have changed, but its expansive observation deck on the 103rd floor still offers some of the best views of the city. Those looking for a thrill can step onto The Ledge, a glass balcony extending out 4.3 feet from the building.

Stop at 875 North Michigan Avenue.

This 100-story building (formerly known as the John Hancock Center) may not be as well known as the Willis Tower, but it's another place for epic city views. There are restaurants, bars, the 360 Chicago observation deck, and occasional events like yoga classes.

Enjoy the free attractions in Millennium Park.

Located in downtown Chicago, Millennium Park is one of the city's largest green spaces. It's easy to spend a few hours here, especially since most of its attractions are free. The Frank Gehry-designed Jay Pritzker Pavilion hosts free concerts and other public events every summer. On a hot day, many cool off in the whimsical Crown Fountain, an interactive public artwork designed by Catalan artist Jaume Plensa.

Take a photo with The Bean.

Chicago is full of public artwork, but this reflective sculpture by artist Anish Kapoor is one of the most recognizable pieces. While the Millennium Park attraction is officially titled "Cloud Gate," most visitors and locals affectionately call it "The Bean."

"Gloud Gate" by Anish Kapoor
Anish Kapoor's "Cloud Gate" sculpture sits in Millennium Park, Chicago, Illinois. Raymond Boyd/Getty Images

Admire Buckingham Fountain.

If you've ever watched Married with Children, this fountain set in sprawling Grant Park at the edge of Lake Michigan is one you'll definitely recognize. Opened to the public in 1927, it's one of the largest fountains in the world.

Take an architecture walking tour.

There are few better ways to experience Chicago's world-famous architecture than on foot. The Chicago Architecture Center offers several different walking tours, including some focusing on the skyscrapers that tower high above the city's streets.

See the animals at Lincoln Park Zoo.

This 35-acre zoo, founded in 1868, is one of the oldest zoos in North America. It's free to visit and hosts an annual holiday lights show.

Go to the theater.

Broadway isn't the only place to catch a show. Chicago has more than 200 theaters, including the well-known James M. Nederlander Theatre and Cadillac Palace Theatre in the Theater District. It's also worthwhile to check out the city's independent stages, such as the Tony Award-winning Chicago Shakespeare Theater at Navy Pier or the innovative Steppenwolf Theatre in Lincoln Park.

Shop the Magnificent Mile.

If you're looking to do some serious damage with your credit cards, look no further than the stretch of Michigan Avenue known as the Magnificent Mile. You'll find a mix of high-end designer stores, sprawling department stores, and more affordable retailers like Marshalls.

Chicago, Illinois: Horizontal shot of the Frank Lloyd Wright Robbie house exterior view, 5757 S Woodlawn Ave, Hyde Park
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Tour a Frank Lloyd Wright house.

If you're a fan of architect Frank Lloyd Wright's work, head to the University of Chicago campus in Hyde Park, where you'll find the Frederick C. Robie House. The house, built in the early 1900s as a single-family home, is a fine example of Prairie School design and is among nearly two dozen homes in the area designed by the famous architect.

See the "Home Alone" house.

You'll need a car to get to this house in the Chicago suburb of Winnetka, but if you grew up on "Home Alone," it'll be worth the drive. You'll recognize it the second you pull up, but remember it's a private residence, so you'll have to appreciate it from the outside.

A general view of ice skaters at Chicago's Millennium Park on March 8, 2013 in Chicago, IL.
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Go ice skating.

Chicago may get cold in the winter, but the joy of ice skating almost makes you forget about the freezing temperatures. From November to March, the Maggie Daley Ice Skating Ribbon in Grant Park and the McCormick Tribune Ice Rink in Millennium Park are popular spots for Chicagoans and visitors.

Catch a cubs game at Wrigley Field.

Wrigley Field is one of the most charming stadiums in baseball. It's home to the former World Champion Chicago Cubs, and if you don't happen to be traveling during baseball season, you can still take a tour.

Learn about the history of Soldier Field.

The nearly 100-year-old Soldier Field is home of the NFL's Chicago Bears. Even if you're not into football, you might recognize it from the Clint Eastwood movie "Flags of Our Fathers" or the television show Chicago Fire. The stadium offers behind-the-scenes tours that pass through the locker rooms, interview room, skyline suite, and other areas.

Ride the Ferris wheel at Navy Pier.

If you're looking for a day of family fun, head to Navy Pier in downtown Chicago. The long pier features rides, games, restaurants, public artwork, and other attractions. Be sure to ride the Centennial Wheel for a truly spectacular view of Lake Michigan.

Take a walk in Oz Park.

There may not be a yellow brick road leading to Oz in Chicago, but there is a park that pays homage to the "Wizard of Oz," which author Frank Baum wrote while living in Chicago. Oz Park on the city's north side features sculptures of all your favorites, including Dorothy, Toto, and the Tin Man.

Old commercial building with statue of liberty frieze on Damen Avenue in Logan Square, a Chicago community on the North Side. No people.
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Explore a Chicago neighborhood.

Chicago is a city of neighborhoods — 77 of them, to be exact. Wicker Park, Bucktown, and Logan Square are worth exploring on the city's north side. On the south side, consider Pilsen and Chinatown. Architecture buffs are sure to appreciate the historical gems they'll find in Old Town.

Visit the DuSable Black History Museum and Education Center.

This Smithsonian-affiliated museum celebrates Black culture and pays homage to Jean Baptiste Point du Sable, the first permanent settler of Chicago. The museum holds more than 15,000 works, including paintings, sculptures, and historical memorabilia, such as the former desk of investigative journalist Ida B. Wells.

Eat your heart out.

Chicago is a foodie paradise that offers something for every palate and every budget. You'll find everything from hot dog joints like Jimmy's Red Hots to Michelin-starred restaurants like Alinea to deep-dish pizza places like Pequod's. Be sure to pack your stretchy pants, and remember, Chicagoans don't ask for ketchup on their hot dogs.

Art on display at the National Museum of Mexican Art in Chicago
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Visit the National Museum of Mexican Art.

This museum in the Pilsen neighborhood is an ideal place to immerse yourself in Mexican art and culture within Chicago's city limits. It's one of few major museums in the U.S. dedicated to showcasing Mexican, Latino, and Chicano art and culture.

Kayak along the Chicago River.

If you're craving an active adventure in the city, you can't go wrong with kayaking on the Chicago River. Urban Kayaks organizes a range of guided excursions, including tours at sunset and during the weekly Navy Pier fireworks show.

Check out the Museum of Contemporary Art Chicago.

Chicago has no shortage of museums, but when it comes to boundary-pushing exhibitions, the Museum of Contemporary Art Chicago (MCA) is second to none. The MCA's permanent collection includes more than 2,000 artworks from the 1920s to the present day, while rotating exhibits, performances, and talks are held throughout the year.

Hop between breweries.

Home to more than 160 breweries, Chicago is often dubbed the craft beer capital of the U.S. From cozy brewpubs to bustling beer gardens, there's something for everyone. Several production facilities, including Goose Island, Revolution Brewing, Lagunitas Brewing Company, and Dovetail Brewing, are also open for tours and tastings.

Stargaze at the Adler Planetarium.

You don't need to leave Chicago to see the stars – just head to the Adler Planetarium on Northerly Island. America's oldest planetarium is a destination for sky shows, exhibits, and special events. As a bonus, it stays open until 10 p.m. on Wednesdays.

Bike along the Lakefront Trail.

Chicago’s Lakefront Trail is a scenic 18-mile paved path along Lake Michigan between Ardmore Street on the north side and 71st Street on the south side. For a fun outing, rent one of the Divvy Bikes and explore it from top to bottom — including a break at one of the beaches along the way.

Chicago River
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Celebrate St. Patrick’s Day.

Chicago's Irish pride beams as bright as the green dye in the river every March. Highlights include the annual Chicago St. Patrick’s Day Parade, river cruises, and food and drink specials at neighborhood pubs. If you're lucky (or a good planner), your trip might coincide with some of the festivities.

Stroll along The 606.

The Bloomingdale Trail Park (The 606) is an elevated recreational trail built on an abandoned railway. Similar to New York's High Line, the 2.7-mile-long path is dotted with public art installations and scenic lookouts. Access points can be found in four of the city's trendiest neighborhoods – Wicker Park, Bucktown, Logan Square, and Humboldt Park – so you can easily hop on or off.

Marvel at art among trees at the Morton Arboretum.

The Morton Arboretum was established in 1922 as a "great outdoor museum" by Joy Morton, founder of the Morton Salt Company. And with more than 1,700 acres and 22,000 plants, it certainly lives up to its mission. The park features rotating large-scale sculpture exhibitions and wellness events like forest therapy and yoga classes, making it well worth the journey 25 miles west of Chicago.

Spend an evening at the American Writers Museum.

Located in the heart of downtown Chicago, the American Writers Museum celebrates the work of historical and present-day writers, from poets to comics to novelists. The museum regularly hosts concerts and special events, including Get Lit museum nights, which bring together bibliophiles for drinks, special tours, and activities on the second Tuesday of every month.

Stop and smell the flowers at the Garfield Park Conservatory.

Garfield Park Conservatory is one of the largest conservatories in the nation, with two acres of public greenhouse space and 10 acres of outdoor gardens. The West Side centerpiece opened in the early 1900s and continues to be a destination for lovers of landscape architecture. In addition to permanent display houses, the conservatory often hosts special exhibits and spring flower shows. 

Learn about the city's criminal history.

Joining a crime tour is a fascinating way to learn about the city's prohibition-era gangsters like Al Capone, Bugs Moran, and Hymie Weiss. Opt for the Gangsters and Ghosts Tour for a storytelling stroll around the Chicago Loop, or board a bus for the Untouchable Tours' Original Gangster Tour led by guides in character as 1920s mafia members.

Admire the skyline from a cruise on Lake Michigan.

While Chicago's river cruises get a lot of attention, sailing around Lake Michigan can be just as fun. Tall Ship Windy offers a variety of cruises aboard a 148-foot, traditional four-masted schooner, including pirate-themed tours and skyline sailings that make the most of the Windy City's namesake weather.

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