Chicago in One Day: An Itinerary

A guide on what to see in the Windy City in the span of 24 hours.

The Chicago “L” Elevated subway, an icon of the Windy City. Photo by Chris K.

Chicago is one of America’s top destinations, a designation that is not unwarranted. Commonly underrated, it is the country’s third-largest city, and as such, offers plenty to see and do. As expected, one day is certainly not enough to see everything, but with proper planning, it can be enough to see most of the major sights and important highlights.

What will follow in this article is a brief guide on the major sights to see in the city, and when. This guide assumes that you have the full day in Chicago, beginning and ending in the Windy City. If you’d like me to do the same for other cities, be sure to Clap for this article, and let me know in the comments or on Twitter @chriskirsch01.

Looking west down the Chicago River, with the Trump tower in the center. Photo by Chris K.

Since you’ll most likely be staying downtown nearby the river, your first destination should be the Chicago Riverwalk. At the heart of the city is the extensive Chicago River which spans the downtown portion of the city, splitting it into two peninsulas. Alongside the banks of the river are pedestrian paths which offer beautiful views of the city and its many draw bridges. Feel free to cross some draw bridges to get some epic river photos.

“The Bean” during the day. Photo by Chris K.

After you spend some time by the River, walk south on either Michigan Avenue or Columbus Avenue to Millennium Park, where you’ll encounter the famous Cloud Gate (a.k.a. “The Bean”) sculpture. Spot yourself on the reflective sculpture and snap some pics, and then head east through the park. Take part in the various activities it has to offer, including picnics and mini golf.

The swinging carousel and Centennial Wheel at the Navy Pier during the day. Photo by Getty Images.

From Millennium Park, head on over to the historic Navy Pier. It’s about a half hour walk, or you can Uber/take mass transit. Once you’re at the Navy Pier, bathe in the sunshine shining through the huge Centennial Wheel, and take a ride on it to get some stunning views of the city. After that, you can walk to the end of the pier and get some lunch, and chill.

View of the Chicago River and a draw bridge during the Architecture Boat Tour. Photo by Chris K.

Conveniently for you, your next destination is located right next to the Navy Pier. You’ll want to take the Architecture Boat Tour, which is a 75–90 minute tour which floats up and down the Chicago River, while offering extensive information about the various skyscrapers, bridges and prominent architecture that the Windy City is known for. The world’s first skyscraper was built here in 1885, so it only makes sense to pay tribute to some of the world’s most iconic structures, skyscrapers, that were born in Chicago.

View of Chicago from the John Hancock Center, looking northeast. On a clear day, you can see into four states. Photo by Chris K.

Following the boat tour, you’re gonna want to get high. No, not like that, I’m talking about literally getting high, high up off the ground at 360 CHICAGO. The boat tour will let you off by the Navy Pier, where you started. From there, walk west to Michigan Avenue, and walk up the famous Mag Mile while gazing at all the high-end retail shops.

Once you reach the John Hancock Center (the giant black skyscraper with the two antennas), go inside and take the elevator up top to get some absolutely stunning views of the city (and if you’re a thrill-seeker, you can TILT over the actual city. Wow).

View from the John Hancock Center in the evening, looking northwest. Photo by Chris K.

Now, you might be wondering why I’m opting for you to visit the John Hancock Center instead of the Willis Tower (Sears Tower) here. If you’re in Chicago for multiple days, I definitely recommend visiting both observation decks, as the views you get from the Willis Tower are also quite stunning.

However, I feel that if you only have one day, the John Hancock Tower takes it. It’s in the center of everything, meaning that your destinations are closer by, and that also makes for more unique viewpoints as you’re not higher than everything. If you only have one day, you can only visit one of these towers, so make your pick (though 360 fits more into this itinerary).

A beautiful deep dish pizza pie from Giordano’s. As a New Yorker, trust me, it’s delicious. Photo by Chris K.

When your time at 360 CHICAGO is complete, a brief walk away from the tower is Giordano’s Pizza at 730 N Rush Street, which is without a doubt the greatest deep dish pizza in the city. Now, I’m not going to get into the whole thin crust versus deep dish pizza debate now (that’s something I did way back in 2018, in one of my earliest articles which was a silly, biased and badly-written piece) but I will tell you that when in Chicago, put that debate aside (and don’t eat the pizza with a fork, eh? There’s no need for utensils!) and get yourself a Giordano’s deep dish pie.

Overview of Wrigley Field during an evening game. Photo by Stephen Green.

There’s no avoiding this one: Wrigley Field in Chicago is as iconic as Rockefeller Center or Coney Island in New York City, or the Santa Monica Pier in Los Angeles. Even if you don’t like baseball, the Cubs and this historic 1914 stadium is a staple of Chicago, and of America, and you definitely don’t want to miss it.

However, like I mentioned in my Philadelphia Itinerary, the only caveat with this one is that you will have to be visiting Chicago during the spring or summer months in order to catch a game, and even then, there’s a chance the Cubs will be away that day, so be sure to check the MLB schedule before you plan your trip.

The great news is that you’re already at Giordano’s, which is two blocks east of the subway station. Get on the iconic Chicago “L” subway, and take the Red Line north to Addison Station, which lets you off right by Wrigley. Once you’re there, take a look around the neighborhood of Wrigleyville before you enter the stadium, which absolutely lights up with activity during games. When you’ve had your fill, head inside the stadium to your seats and enjoy the classic ballgame that is to come.

The Chicago Theatre at night. Photo by Chris K.

When that’s all over, head back to the train and take it back to your hotel (or, if you’ve had your fill for the day, an Uber would suffice). But if you take the Red Line back, get off at Lake Street and gaze at the iconic illuminated Chicago Theatre, and get yourself an epic snapshot like the one above. That puts a nice bow on your one day in Chicago, and you’ve earned some rest and relaxation (or some clubbing and bar-hopping. Up to you).

If you would like me to create a one-day itinerary for other cities, be sure to Clap for this article, and let me know in the comments or on Twitter @chriskirsch01.

Chris is a writer and publisher who travels America, and loves doing it. He also loves pizza, video games, and sports, and can tell you a thing or two about each. Follow him on Twitter and on Medium to be informed of new articles.

Note that all images in this article are property of Chris K. unless otherwise noted. These images may not be used without permission.

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Chris K

Native New Yorker. Pizza, Sports, Games, Life. Writing about whatever my heart desires. Follow me here and on Twitter for more articles!