The Most Popular Things to See and Do in Chicago

Photo courtesy of Photo courtesy of Choose Chicago
Photo courtesy of Photo courtesy of Choose Chicago
Photo courtesy of Photo by Jamie Bartosch
By Jacky Runice, Chicago Local Expert

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. Wherever your interests lie, the city offers memorable things for you to see and do. The city’s excellent public transit system, Divvy bike share program, and accessible lakefront trail make it easy to get from one part of Chicago to the other.

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 nd 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. 

10. Lincoln Park Zoo
Photo courtesy of grendelkhan

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.

9. Navy Pier
Photo courtesy of jlwelsh

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, IMAX movie theater, Broadway-quality Shakespeare plays, 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 is brand new and 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.

8. Art Institute of Chicago
Photo courtesy of The Art Institute of Chicago, Mr. and Mrs. Frank G. Logan Purchase Prize Fund.

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.

7. Adler Planetarium and Astronomy Museum
Photo courtesy of Adler Planetarium

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.

6. 360 Chicago Observation Deck
Photo courtesy of John Hancock Observatory

After 40 seconds in the John Hancock Building'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. Food and drink are available in the restaurant and lounge, and informational exhibits are on display in four different languages. Should you be around in April, you can run up the stairs to the top in the popular "Hustle up the Hancock," which benefits the Respiratory Health Association. 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 the 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.

5. Wrigley Field

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 expensive 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." If the Cubs are on the road, take a tour of Wrigley Field, which includes visits to the dugout, locker rooms and the field.

4. Second City
Photo courtesy of Photo courtesy of Choose Chicago

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 wth 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 its 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.

3. Chicago Architecture Foundation River Cruise
Photo courtesy of Photo courtesy of Choose Chicago

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 unique tours, the CAF 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 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.

2. Chicago Lakefront Trail
Photo courtesy of Photo by Jamie Bartosch

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. Expect to slow down around Navy Pier, one of the most congested points on the trail. The Lakefront Trail Separation project will divide bike and pedestrian paths and is expected to be complete by the end of 2018.

1. Millennium Park
Photo courtesy of Harold Rail

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!