Iconic Chicago: the city's most popular things to see and do

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

Music, art, food, culture, or sports ... whatever your interests are, Chicago's got amazing things for you to see and do. The city’s excellent public transit system, Divvy bike share program, and accessible lakefront trail makes it easy to get from one part of Chicago to the other. Plus there are taxis and Uber drivers everywhere.

Since the cold, snowy Chicago winters can test even the hardiest humans, the best time to visit the city is in the spring, summer and fall. That way you can see Chicago’s many attractions is 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 crossroads of today.

Using Chicago’s Lakefront Trail, it’s easily 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.

For a different kind of attraction, see a show at Second City, the same comedy troupe that launched the careers of comedians including Gilda Ratner, John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others.

10. Lincoln Park Zoo
Photo courtesy of grendelkhan

An ape house, a 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 an endangered Siberian tiger. The Zoo is open 365 days a year and constantly hosts events and activities.

9. Navy Pier
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This downtown pier that extends into Lake Michigan was once used by the military. Today, it's Chicago's largest tourist hub. You can just walk up and down the pier, taking in the gorgeous skyline and lake views. Or you can visit the excellent children's museum, the IMAX movie theater, the Broadway-quality Shakespeare plays, dance in the grand ballroom, or ride their new Centennial Wheel, a 200-foot-high ferris wheel with enclosed gondolas. There are plenty of boat ride options, too, including the Tall Ship and dinner cruises. In the evening, if the weather's nice, you can watch a free fireworks show synchronized to music on Wednesday and Saturday nights.

8. Art Institute of Chicago
Photo courtesy of The Art Institute of Chicago

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. The contemporary section has been expanded and now includes pieces by Picasso, Matisse, Dali, Pollock, and Warhol. 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

This eye-catching, twelve-sided building includes two sky theaters, one of which was the first planetarium in the western hemisphere. The theaters depict the night sky and allow visitors an up-close look at distant planets, moons and galaxies. The complex also features exhibition rooms, a cafe and a StarRider theater that offers amazing, interactive, virtual reality shows. In it, visitors use controls in their seats' armrests to participate in a 3-D simulation of space travel. On family-friendly Far Out Fridays, visitors get to see shows, sit in on lectures, view the night sky, play games and learn how to set up and use a telescope.

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

After 40 seconds in John Hancock's elevator, visitors are transported 1,000 feet above Chicago. From there, the city'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 haven't won a World Series in more than 100 years (but 2016 could be the year!). 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, it's 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
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The world's premier comedy troupe, The Second City has launched some of the biggest names in the business, including Gilda Radner, John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others. So it's likely that the comedic actors you see in these shows will soon be featured in movies, commercials and "Saturday Night Live." The improv comedy shows poke fun at current-event and societal topics. There are almost no costumes or props involved, and the stage is in front of a small area of tables and chairs. While The Second City is the main stage, you can also see outstanding comedy at the second-tier Second City etc. and the Up Comedy Club, located in the same building.

3. Millennium Park
Photo courtesy of © Cesar Russ Photography

Millennium Park is Chicago's crown jewel. Summertime means a stellar line-up of concerts at Jay Pritzker Pavilion (during the day, on most Tuesdays through Fridays, the Grant Park Orchestra and Chorus can be heard for free in the Pavilion as musicians rehearse for upcoming concerts). Winter brings out the ice-skating rink and Christmas lights. Get a picture with the Cloud Gate sculpture, or 'The Bean' as we call it in Chicago. You can also watch water spew from two 50-foot glass block towers at each end of a shallow reflecting pool. The towers project video of faces of Chicago citizens on LED screens and having water flow through an outlet in the screen to give the illusion of water spouting from their mouths. At the southern tip is Lurie Garden, a 5-acre urban oasis featuring perennials, bulbs, grasses, shrubs and trees.

2. Chicago Architecture Foundation River Cruise
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Seeing Chicago's architectural beauty 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. Guests will learn about more than 50 buildings and their significance to Chicago's architectural landscape as well as general history about Chicago and how it grew from a small back-country outpost to one of the world's most important crossroads of today. Tours are available late April through mid-November and run about an hour and a half in length. Be sure to purchase tickets in advance as they often sell out.

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

With skyscrapers on one side and the lake on the other, this 18.5-mile walking, running and biking path is one of the city's most scenic places. The paved, linear path runs along Lake Michigan, stretching from the far north part of the city to the South Side. Neighborhoods and attractions dot the path, including the Museum Campus (home to several museums), Soldier Field (home of the Chicago Bears), Buckingham Fountain, Lincoln Park Zoo, Oak Street Beach, and the South Shore Cultural Center. The path gets crowded during warm weekends. Expect to slow down downtown. Bike rentals are available near every path entrance.