Chicago in One Day: An Itinerary

The Chicago “L” Elevated subway, an icon of the Windy City. Photo by Chris K.
Looking west down the Chicago River, with the Trump tower in the center. Photo by Chris K.

1. Chicago River (8:00 a.m. — 9:00 a.m.)

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.

2. Millennium Park (9:30 a.m. — 10:30 a.m.)

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.

3. Navy Pier (11:00 p.m. — 12:00 p.m.)

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.

4. Architecture Boat Tour (12:00 p.m. — 1:30 p.m.)

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.

5. John Hancock Center / 360 CHICAGO (2:30 p.m. — 4:00 p.m.)

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.

View from the John Hancock Center in the evening, looking northwest. Photo by Chris K.
A beautiful deep dish pizza pie from Giordano’s. As a New Yorker, trust me, it’s delicious. Photo by Chris K.

6. Deep Dish Pizza at Giordano’s (4:30 p.m. — 5:30 p.m.)

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.

7. Cubs Game at Wrigley Field (6:30 p.m. — 10:00 p.m.)

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.

The Chicago Theatre at night. Photo by Chris K.



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Chris K

Chris K

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