Things to do in Chicago, IL

Chicago cityscape

Chicago, the biggest city in the Midwest and third largest in the United States, is home to nearly 3 million people. A thriving multicultural city, Chicago is known primarily for its architecture, sports, music, and food. Some of the best things to do in Chicago are located right downtown. And part of the beauty of Chicago is its centralized location; Chicagoans are a short to moderate drive away from all sorts of fun activities. Let us help you find lots of cool things to do in Chicago for singles, couples, or families!

Top Attractions in Chicago, IL

Willis Tower

Many of the top things to do in Chicago are centered around the city's North Side and central downtown area. Two of the most iconic Chicago destinations are the Willis Tower (formerly known as the Sears Tower) and the John Hancock Center, two of the largest skyscrapers in a city full of them. At Willis Tower, the second-tallest building in the United States, visitors can experience views of the city and beautiful Lake Michigan on the Skydeck and in glass boxes referred to as "The Ledge." On a clear day, you can see as far as Indiana, Michigan, and Wisconsin from the Skydeck. The John Hancock Center features the famous Signature Room restaurant and an observatory platform of its own, 360 Chicago. The observatory has a bar, a multimedia exhibit, weekly special events, and the thrill ride TILT, which suspends viewers at an angle over a magnificent view of the city. While visiting John Hancock Center and Willis Tower are considered some of the more touristy things to do in Chicago, even longtime residents of Chicago should give these unforgettable experiences a chance.

Another top attraction in Chicago is Navy Pier. Located on the shores of Lake Michigan, Navy Pier features a replica of the world's first Ferris wheel as well as a number of other carnival rides, games, and an interactive maze experience called Amazing Chicago. The pier is also home to several restaurants and shopping locations, a beer garden, a movie theater, and a live music stage. You can find the starting point for many of Chicago's walking, bicycle, bus, helicopter, and boat tours at Navy Pier. Twice weekly from Memorial Day to Labor Day, Navy Pier ends the day with a fabulous fireworks display! You can view the fireworks from the pier or book a cruise and watch from the water.

Cloud Gate

Millennium Park is another must-see in downtown Chicago. Located in the Loop neighborhood, Millennium Park was completed in 2004 and borders another popular Chicago park, Grant Park. Public art is an important feature of Millennium Park, most notably "Cloud Gate," the famed bean-shaped steel sculpture by British artist Anish Kapoor. It is very popular among tourists and residents alike as a photo (and selfie!) spot due to the reflective nature of the piece. Elsewhere in the park, enjoy the Crown Fountain installation, Lurie Garden, an indoor bicycle center, the Harris Theater, and live music performances at the Jay Spritzer Pavilion.

Fun Things to Do Downtown

While we got you started with three of the most popular attractions, there are many more fun things to do in downtown Chicago. Chicago has a strong performing arts tradition and is home to a vast number of theaters and music venues. For those who love theater, ballet, and opera, check out venues like The Chicago Theatre, Oriental Theatre, Mercury Theater, Apollo Theater, and Navy Pier's Chicago Shakespeare Theater. If live music is more your thing, we recommend classic jazz and blues venues like the Green Mill, Andy's Jazz Club, Buddy Guy's Legends, and Kingston Mines.

In the mood for some shopping? You will definitely want to check out the Magnificent Mile. Spanning a good portion of North Michigan Street, the "Mag Mile" is the retail center of Chicago, featuring scores of nationally and internationally recognized brands. You'll also find three sizable indoor shopping malls: Water Tower Place, The Shops at North Bridge, and 900 North Michigan Shops. In addition to shopping, the Magnificent Mile features luxury hotels, fine dining experiences, and many of Chicago's largest skyscrapers.


Wrigley Field

Sports fans know that Chicago is a passionate sports town. And one of the things we love most about Chicago sports is that all of the major teams are located right downtown! Baseball fans can enjoy two teams with an illustrious history: the Chicago White Sox play at Guaranteed Rate Field in Chicago's South Side, while the North Side is home to the Chicago Cubs at historic Wrigley Field. In the Near South Side neighborhood, on the shore of Lake Michigan, sits Soldier Field: this open-air football stadium is home to the Chicago Bears, known locally as "Da Bears." And finally, head to East Garfield Park to the United Center, where you can cheer on the Chicago Bulls on the court or watch the Chicago Blackhawks take the ice. The United Center is also a frequent destination for popular music acts on tour.

Romantic Date Ideas and Nightlife

There are lots of fun and romantic things to do in Chicago if you're looking for ideas for date night. Many couples like to take advantage of Chicago's thriving culinary scene. Enjoy fine dining experiences at highly rated restaurants like Oriole, Alinea, and Joe's Seafood, Prime Steak, & Stone Crab. For more moderately priced options, we recommend The Chicago Diner, Smoque BBQ, Antique Taco, and Portillo's. You can also head to Chicago's Chinatown for authentic Cantonese cuisine. And of course, no time spent in Chicago is complete without sampling Chicago-style deep-dish pizza. Some highly-rated options include Spacca Napoli, Lou Malnati's, Giordano's, and Pequod's.

Logan Square, a great place to find good restaurants, is also the home to many popular bars. And after hitting the bar, there are plenty of things to do in Chicago at night that will make it a date night to remember! Check out the Neo-Futurarium to take in a unique theater experience, or make your date laugh at one of Chicago's famous comedy clubs. Chicago is an important city in the history of improvisational comedy, which you can enjoy at clubs like the iO Theater and The Second City. After dinner and a show, take your date on a romantic evening cruise with one of the city's night-time boat tours. The lights of the city by night are a sight to behold!

Solo Activities for Singles

Record Shopping

Need some time to yourself? Never fear! You'll find lots of unique things to do in Chicago alone. For some retail therapy, enjoy some of Chicago's unique thrift shopping experiences. Stores like Knee Deep Vintage, Dusty Groove, and Myopic Books are great places to explore on your own. For the thrill-seekers among us who can't talk a friend into joining them, experience iFly Indoor Skydiving in the trendy Lincoln Park neighborhood. Feel like taking it easy instead? Pamper yourself and enjoy some "me time" at one of Chicago's luxury spa experiences. The spas at the Peninsula and Four Seasons hotels are popular choices, as are the AIRE Ancient Baths, modeled after a Roman bathhouse. For a more unique experience, try one of the sensory deprivation tanks at Float 60.

Thing You Can Do for Free

LionLow on cash? Don't fret: There are lots of things to do in Chicago for free. Most of Chicago's public parks and art exhibits are free to wander as you see fit, like the beautiful Buckingham Fountain and expansive Grant Park. Many museums in the Chicago area offer free days, and some, like the Chicago Design Museum and Museum of Mexican Art, are free year-round. In a similar vein, the Chicago Cultural Center offers free admission and features historical exhibits, theater and music performances, and events throughout the year. A very popular free attraction with families is the Lincoln Park Zoo and Conservatory. The conservatory features more than 40,000 species of plant life in four buildings. The zoo allows visitors to observe many endangered species from around the world, such as polar bears, lions, rhinos, gorillas, and snow leopards.


Family-Friendly Activities for Kids and Toddlers

Families can enjoy lots of fun and child-friendly activities around the city. One of our favorite things to do in Chicago with kids is visit the Chicago Children's Museum. Located adjacent to Navy Pier, the museum features lots of interactive exhibits and learning opportunities for kids of all ages, including toddlers. The Chicago Children's Theatre is another popular kid-centered venue, featuring family-friendly theater, summer camp programs, and various seasonal events and classes.

Some more things to do in Chicago with family include taking an Urban Adventure Cruise, a fully narrated boat tour of the city that prides itself on being family-friendly. Kids and teens also love Maggie Daley Park, featuring an expansive Play Garden and a rock climbing wall.

Outdoor and Seasonal Attractions

While Chicago is an urban environment, nature-lovers will find plenty of outdoor things to do in Chicago in all seasons of the year. Chicago is rated as one of the most walkable cities in the country, with plenty of parks and green space. Cycling has taken off in Chicago, with companies like Divvy offering bike-share programs and rentals, a perfect option for city-dwellers who may not have the garage space to own and maintain their own bicycle. The Lakefront Trail, a picturesque pedestrian and bike path along the shores of Lake Michigan, and The 606, an elevated highway repurposed for bicycles, are very popular with cyclists.

Some of our favorite outdoor activities in Chicago take advantage of Lake Michigan and the Chicago River. Chicago Sailing offers lessons in how to sail, as well as sailboat rentals. Companies like Urban Kayaks and Chicago River Canoe and Kayak offer canoe and kayak rentals at the lake or the river. Chicago's beaches are also a great choice for lovers of the outdoors. We recommend North Avenue Beach and Margaret T. Burroughs Beach.

Chicago River on St. Patrick's DayChicago offers many seasonal events and festivals that will keep you and your family busy all year long! Some fun things to do in Chicago in the winter include ice skating at Millennium Park, taking advantage of deals and specials during Chicago Restaurant Week in January, seeing the beautiful holiday light show at the Lincoln Park Zoo or the similar Wonderfest at Navy Pier, and taking your kids to Polar Adventure Day at Northerly Island near Grant Park. In the spring, Chicago is known for its incomparable St. Patrick's Day parade, for which the city dyes the Chicago River green to honor its Irish heritage. Other popular spring events include Baconfest and the Chicago Critics Film Festival.

Looking for cool things to do in Chicago in the summer? We've got you covered. The Chicago area plays host to the world-famous Lollapalooza music festival every summer, a sizable Pride celebration in June, the Craft Beer Festival in July, the annual Chicago Blues Festival and Chicago House Music Festival, the Windy City Ribfest, the Taste of Chicago street food festival, and, of course, the annual Fourth of July fireworks. When fall arrives, check out the Chicago Jazz Festival, the alternative music festival Riot Fest, the annual Chicago Marathon, and Chicago's impressive Thanksgiving Parade.

Indoor Activities for a Rainy Day

Field Museum T-Rex

That being said, sometimes, you need to find things to do in Chicago on a rainy day. Luckily, there are plenty of options. We recommend taking advantage of some of Chicago's cultural and educational centers. The Adler Planetarium is an excellent choice, offering several different family-friendly daytime programs and adult-oriented "after dark" events. The castle-like Chicago Water Tower is another fun place to tour on a rainy day. The historic Gothic Revival-style structure is a jewel of Chicago architecture and contains exhibit spaces to showcase local history and culture. If you've already checked out Lincoln Park Conservatory and are eager for another botanical garden experience, the Garfield Park Conservatory is a great choice that's entirely indoors. Are fish more your speed? Check out the Shedd Aquarium to see more than 32,000 fish, aquatic mammals, reptiles, penguins, and even monkeys!

Perhaps the best things to do indoors in Chicago involve visits to the city's many museums. The Field Museum is an absolute must-see. Dedicated to the study of natural history, some of the Field Museum's most popular permanent exhibits include the DNA Discovery Center, a replica of a Pawnee lodge, an extensive collection of East Asian jade art, an Egyptian mummy exhibit, and one of the largest dinosaur collections in the United States. The dinosaur exhibit is home to "Sue," one of the largest T. rex specimens in the world! Some of Chicago's other notable museums include the Museum of Science and Industry, the Jane Addams Hull-House Museum, the Chicago History Museum, the Art Institute, and the American Writers Museum. Check out the museums' websites to learn more about the exhibits currently on display.

Chicago's Suburbs: Nearby Illinois Attractions

Lego Bricks

If you're looking for things to do in the Chicago suburbs this weekend, rest assured that the greater Chicago area has a lot to offer outside of downtown. Some popular destinations just a short distance away from the city include the Frank Lloyd Wright Home in Oak Park, Brookfield Zoo in nearby Brookfield, the summer-only Ravinia Festival of music in Highland Park, and the Illinois Holocaust Museum in Skokie. Families will love Six Flags Great America in Gurnee and Legoland in Schaumburg; both are popular destinations with kids but fun for the whole family. Fans of racing can catch a horse race at Arlington International Racecourse in Arlington Heights, a drag race at Route 66 Raceway in Elwood, or a NASCAR race at Chicagoland Speedway in Joliet. For a more traditional sports experience, Toyota Parkin Bridgeview is home to the Chicago Fire, the city's Major League Soccer team.

Abraham Lincoln HomeIf you are willing to drive a couple of hours farther, there are lots of things to do in Illinois outside of Chicago that make great weekend road trips. Cahokia Mounds is a unique site where you can experience the huge earthen mounds that are the remains of an ancient Mississippian city. It's one of the oldest human-made structures in the country! History buffs will also love Springfield, the capital of Illinois. You can tour the old Illinois State Capitol and Illinois State Museum as well as many sites devoted to President Abraham Lincoln: the Lincoln Presidential Library and Museum, the Lincoln Home National Historic Site, the Lincoln-Herndon Law Office, and the Lincoln family tomb in Oak Ridge Cemetery. Outdoor enthusiasts might consider a road trip to Starved Rock State Park, which offers hiking, camping, and a picturesque lodge. A bit farther from Chicago, Shawnee National Forest features more challenging hiking trails and lots of wildlife-spotting opportunities, especially the forest's many bald eagles. Not far from Shawnee, Superman fans can drop by Metropolis to visit The Super Museum!

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