Best Things to Do in Chicago

The most popular things to see and do in Chicago

Chicago may have been a "toddling" town when Sinatra visited in the mid-20th century, but it has developed into a world-class grown-up full of music, art, food, culture and sports. In fact, Condé Nast Traveler’s Readers’ Choice Awards has named Chicago the best large city in the US for the last four years. Wherever your interests lie, there are memorable things for you to see and do. The city’s excellent public transit system, Divvy bike share program, and an accessible lakefront trail makes it easy to get from one part of Chicago to the other. Visitors might consider purchasing a Chicago CityPASS for half off of five of the city's top attractions. 

Millennium Park is one of the most extraordinary public spaces in the world. The Art Institute is home to one of the best and most diverse art collections on the planet. Since cold, gray Chicago winters can test tourists, the best time to visit may be in the spring, summer and fall. That way you can see some attractions and get the lay of the land by boat. The Chicago Architecture Foundation’s River Cruise takes visitors along the Chicago River while knowledgeable docents share the history of Chicago, its architecture and how it became one of the world's most important metro areas. Visit 360 Chicago on a clear day to see the spectacular architecture and shoreline from the 94th floor of the John Hancock Building with a tilting glass lookout 1000 ft. up.

Using Chicago’s Lakefront Trail, it’s possible to stop along the route and view the Monet paintings at The Art Institute or take a picture with The Bean at Millennium Park.

Don't leave without seeing a show at Second City, the same comedy troupe that launched the careers of comedians including Steve Carell, Stephen Colbert, Tina Fey and many other successful comedic talents. 



The only Chicagoans you'll run into at Navy Pier are the employees but out-of-towners and suburbanites seem to love the downtown pier that extends into Lake Michigan. Once used by the military, it's now Chicago's largest tourist attraction. You can just walk up and down the pier, taking in skyline and lake views. Or you can visit the excellent children's museum, Chicago Shakespeare Theater, or ride the Centennial Wheel, a 200-foot-high Ferris wheel with enclosed gondolas. There are plenty of boat ride options, too, from the zippy Seadog to a more stately Odyssey. In summer, you can watch a free fireworks show synchronized to music on Wednesday and Saturday nights. An "old Chicago" style IT'SUGAR store offers a "Taste of Chicago Box" featuring products that originated here including Tootsie Rolls®, Baby Ruth®, Juicy Fruit®, Charleston Chew®, Chuckles®, Sugar Daddy®, and others.

Recommended for Best Attractions & Activities because: Chicago's most popular tourist destination includes a new 200-foot-tall Ferris wheel, which opened in 2016.

Jacky's expert tip: Sable at Navy Pier recently opened offering comfortable accommodations, dining at Lirica and a rooftop bar - all with sweeping views.

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Located east of Lake Shore Drive, the Lakefront Trail is an 18.5-mile linear path that stretches from the far north part of the city to the south side. Neighborhoods dot the path as well as notable cultural landmarks including the Museum of Science and Industry; the Field Museum; Shedd Aquarium; Adler Planetarium & Astronomy Museum; the Chicago Children's Museum; the Peggy Notebaert Nature Museum; Lincoln Park Zoo, and the South Shore Cultural Center. The paved path is very popular among walkers, joggers and bicyclists and it will and does get crowded during warm weekends (to the tune of 100,000 a day on a sunny summer weekend). Expect to slow down around Navy Pier, one of the most congested points on the trail. The Lakefront Trail Separation project divided bike and pedestrian paths so walkers and runners no longer annoy each other.

Recommended for Best Attractions & Activities because: The lakefront trail is one of Chicago's best natural attractions, and it's free!

Jacky's expert tip: Metered parking is available at almost all of the parks along the trail.

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Even rocket scientists have a hard time envisioning the size and composition of the ever-expanding universe, so imagine the task for kids who get space info from Pixar. The Adler Planetarium & Astronomy Museum, the nation's very first planetarium, sends families forth on a voyage of planetary discovery through more than 35,000 square feet of exhibits, two full-size planetarium theaters, workshops, camps and special family programs. It's a starry, starry night and day as educators lead demonstrations, telescope viewing, crafts or exhibit interpretation almost every day. Adler's historic Sky Theater has been accurately recreating the night sky on its dome since 1930 and the world's first StarRider Theater is a completely digital, virtual outer space environment that allows you to actively participate by operating controls on seat armrests.

Recommended for Best Attractions & Activities because: Founded in 1930, the museum offers plenty of interactive experiences for even the most challenged attention span.

Jacky's expert tip: After looking at the sky, turn your gaze outdoors, the Adler was voted "Best View of Chicago" by the American Institute of Architects.

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After 40 seconds in the former John Hancock Center's elevator, visitors are transported 1,000 feet above the city and to 360 CHICAGO Observation Deck on the 94th floor. From there, Chicago's third-largest building offers views that stretch out to 80 miles on a clear day. Informational exhibits are on display in four different languages. BAR 94 is Chicago's highest bar featuring local brews from Revolution and cocktails with spirits by KOVAL Distillery. You could also make reservations in advance for dinner or stop for a drink at the famous The Signature Room at the 95th, where you can continue to enjoy spectacular views. Adventure seekers will want to try TILT, a one-of-a-kind feature that lets you stand in a glass box as it tilts over the top of the skyscraper and affords you downward facing views from 1,030 feet up.

Recommended for Best Attractions & Activities because: Open 365 days a year, 360 Chicago allows views up to 80 miles away on a clear day.

Jacky's expert tip: 360 CHICAGO just added Magnicity, an App that offers a touch-free, 3D, self-guided tour of Chicago's notable landmarks and info about Lake Michigan.

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An ape house, birdhouse and a working model of a five-acre Midwestern farm are just a few examples of what makes this zoo special. Founded in 1868 and known as America's oldest free public zoo, the Lincoln Park Zoo still manages to charge no admission and remains open year-round. Set on scenic park grounds with lush lawns and pleasant walkways, the zoo greets visitors with the beauty of Georgian Revival buildings and a spectacular greenhouse. Prominent zoo residents include elephants, giraffes, sea lions, gorillas, reptiles and the Red Wolf, now one of the most endangered canids in the world. Where else can you see a lesser Madagascar hedgehog tenrec on Thanksgiving Day or a playful polar bear in the middle of July? The Zoo constantly hosts events and activities so check the web site.

Recommended for Best Attractions & Activities because: The free zoo is set within the heart of Chicago and is open 365 days. Visitors can enjoy seeing the animals in award-winning habitats.

Jacky's expert tip: Check the website for announcements on new arrivals. Everyone loves furry or feathered newborns.

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This century-old ballpark is home to the Chicago Cubs, who finally paid back diehard fans with a World Series win in 2016 (the previous one was in 1908). The party neighborhood around it is known as "Wrigleyville," full of restaurants and bars. The ballpark is famous for its ivy-covered brick walls in the outfield, its iconic red sign, the manually operated scoreboard, and its giant troughs in the men's bathroom. Expect long lines and stadium prices for food and beer. You'll want to stand and sing "Take Me Out to the Ballgame" with the crowd during the 7th inning stretch. Fans will wave white "W" flags when the Cubs win and sing "Go Cubs Go." To book a guided tour to see the dugout, press box, bleachers and the field, For more information, check out the Wrigley Field tours website.

Recommended for Best Attractions & Activities because: This is one of the country's most famous and historic ballparks.

Jacky's expert tip: If you're sitting in the bleachers and catch a home run ball hit by the opposing team, you'll be expected to throw it back onto the field. It's a Wrigley Field tradition.

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Who doesn't need a few laughs during the cultural chaos that is life in the USA? The world's premier comedy theatre and school of improvisation, Second City, pokes fun at boomers, millennials, media, and the *&%#@! going on in DC. Everyone with a pulse knows that Second City launched some of the biggest names in the business, including Steve Carell, Stephen Colbert, Tina Fey and countless others. Since its creation in 1959, the show claimed Old Town it's home when the founders wanted a theater to practice their own, Chicago-style routine of sketch and improv. The small audience is packed in front of a sparse stage with only a few chairs, and the show covers current topics, followed by some improv using audience-suggested topics. If the main stage is sold out, don't hesitate to see Second City, etc.or some stand up at adjacent Up Comedy Club.

Recommended for Best Attractions & Activities because: The Second City has launched some of the biggest names in the business including Tina Fey and Stephen Colbert.

Jacky's expert tip: If tickets are sold out, you can try Second City, etc., or the Up Comedy Club, located in the same building.

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Seeing Chicago's architectural stunners from the decks of a river cruiser is a must for both locals and visitors. One of the city's most satisfying tours, the CAC River Cruise takes visitors along the north and south shores of the lake in about an hour and a half. Guests will learn about more than 50 buildings and their significance to Chicago's architectural landscape as well as general city history and how it grew from a modest Midwestern outpost to one of the world's most important crossroads. You'll get the 411 on Chicago's brilliant architecture and its history in 90 minutes.Tours are available late April through mid-November. Be sure to purchase tickets in advance as they often sell out. Go to the southeast corner of the Michigan Avenue Bridge at Wacker Dr. and look for the blue awning marking the stairway entrance.

Recommended for Best Attractions & Activities because: CAC River Cruise tours take cruisers along the north and south shores of Lake Michigan to learn the significance of more than 50 buildings.

Jacky's expert tip: Tickets for the city's #1 tour sell out so book them as soon as you can.

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A highlight of any trip to Chicago, this museum is home to one of the best and most diverse art collections in the world. People are drawn first to the vast Impressionist collection, including the world's largest group of Monet paintings. But treasures abound, including the haunting "American Gothic" and Seurat's groundbreaking Pointillist work. See pieces by Picasso, Matisse, Dali, Pollock, and Warhol. Designed by architect Renzo Piano, the Modern Wing is home to the museum's collection of 20th- and 21st-century art. The temporary shows are also well known and always receive critical acclaim. Kids particularly enjoy the Thorne Rooms, 68 miniature room models with intricately detailed European interiors from the 16th century through the 1930s as well as American furnishings from the 17th century to 1940.

Recommended for Best Attractions & Activities because: Visitors to the Art Institute of Chicago can view the haunting "American Gothic" and Seurat's groundbreaking Pointillist work.

Jacky's expert tip: In addition to the world's largest Monet collection, explore the museum's Modern Wing for one of the world's great collections of modern and contemporary art.

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Millennium Park is one of the most extraordinary public spaces in the world. More than a park, it is a breathtaking showcase for the visual and performing arts and a permanent homage to the vitality and creativity of this world-class city. The centerpiece of the park is the Frank Gehry-designed Jay Pritzker Pavilion, the most sophisticated outdoor concert venue of its kind in the United States. You can't miss one of the world's largest outdoor sculptures by British artist Anish Kapoor and the Crown Fountain designed by Spanish artist Jaume Plensa. Be sure to admire the Lurie Garden, a distinctive blend of spatial structure, plantings and lighting. Summer brings a stellar line-up of concerts at Jay Pritzker Pavilion and the ice-skating rink and Christmas lights emerge every winter. Everyone is welcome to snap a selfie at the Cloud Gate sculpture, or 'The Bean.' Pack a picnic lunch and enjoy!

Recommended for Best Attractions & Activities because: In the middle of downtown, it's a nice place to meander, catch a free concert or take a selfie at the reflective 'Bean.'

Jacky's expert tip: The ice skating rink is open to the public and is free if you have your own skates. Rentals are available at the rink for a charge.

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Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky