Many good Chicagoans will tell tourists to start at Navy Pier. The pier is a shining example of Chicago innovation, with its large ballroom, plethora of restaurants, and, of course, the Centennial Wheel, which offers one of the best views of the city. Make sure to grab a few kitschy Chicago souvenirs before heading out, as Navy Pier is the crème de la crème of jokey gear. Consider the pier your warm-up before moving on to the DuSable Bridge.
Although many tourists don’t realize it, DuSable bridge is shown in many movies and TV shows that take place in Chicago. However, its main selling point is the view of the Chicago River, one of the most underrated attractions in the city. Visit the bridge to enjoy the river in all of its glory.
By this time, you’re going to need some food! Let’s be honest, no Chicago trip—no matter how fast—is complete without some deep-dish pizza. The rivalry among Chicago pizzerias runs deep, so make sure to go to Giordano’s because it’s one of the best. Seriously. But do be sure to call ahead and reserve a table—no matter what time of day or year, Giordano’s is always packed, but it’s worth the wait and not to be missed while walking around the city.
After filling up at Giordano’s, it might be good to knock off one of the most touristy (and most picturesque) spots in town. Cloud Gate, more affectionately known as “The Bean,” is the strange sculpture that reflects the city skyline. It’s perfect for your next profile picture or Insta post, as it’s nearly impossible to get a bad picture in front of it. For those brave enough to take the walk during the winter months, pictures in front of Cloud Gate will feature a silver-toned city and barely any tourists.
Many Chicago visitors are fans of Ferris Bueller’s Day Off , and what better way to pay homage to the film than to traipse around the Art Institute of Chicago, and take pictures in front of some of the world’s most iconic works of art. If you’re not a film buff, the Institute is still a phenomenal place to waste a bit of time looking at pieces by everyone from Monet to van Gogh … or to warm up, if it’s winter.
This is an unmissable stop during a summertime walk in Chicago, as there are few places as beautiful as Grant Park and Buckingham Fountain in June and July. The fountain construction is reminiscent of European architecture and is simply breathtaking. If you’re in town for the Taste of Chicago, it’s the best place to enjoy a cupcake or hot dog.
For kids—or the young at heart—Shedd Aquarium is the among the greatest places in Chicago. The Shedd, Adler Planetarium, and The Field Museum could be grouped together, as they’re sometimes known as Museum Campus. However, each venue has something unique to offer. At Shedd, it’s the free walk around the upper floor, where patrons witness all sorts of awesome animals and even get to pet a few! Every Wednesday during the summer, the aquarium hosts Jazzin’ at the Shedd, where attendees enjoy a drink and some music while visiting the animals.
Adler Planetarium is perfect for those dreaming of a world beyond our own. Take in a show in the Definiti Theatre, check out one of the many astronomy exhibitions, or stop by Astro Overnights, an absolute must for anyone interested in the stars, especially families. Enjoy a bite at Galileo’s Café for lunch or dinner right at the edge of Lake Michigan, which makes for a spectacular views and even better people watching.
For all of the Jurassic Park  fans, The Field Museum will satiate any dinosaur lover’s soul. With fascinating exhibits both ancient and contemporary, the museum curates each exhibit with care. It’s a great finale to the Museum Campus trifecta.
Soldier Field is home to the Chicago Bears, which is a point of both hometown pride and anguish. Although the Bears have been deplorable the past few years, the fans are incredibly dedicated. So, dedicated, in fact, that ESPN made a TV show about them. Taking in a game at the iconic stadium is the perfect way to end this walking trip. Watching a Bears game is sure to get you into the Chicago spirit!