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How To Explore Chicago In 24 Hours

Tom Malone/Adventure Tribune
Sometimes, we find ourselves in a new city with very little time to explore it to its full potential. With only 24 hours in a new place, what's an adventurer to do?


Recently, I touched down in Chicago with 24 hours of free time before my departure. Obviously, one day isn’t nearly enough time to fully explore a city, but with some solid walking shoes and dedication, I certainly tried.

Before I arrived, I mapped out my route so that I could make the most of my 24-hour deadline. I worked my way from South to North on foot (mostly) and walked over ten miles, but the views and experiences were entirely worth it.

Everywhere I went, I interacted with friendly people from the city, excited adventurers from all parts of the world, and a brisk Lake Michigan wind. The adventure began here:

The Bean at Grant Park
The Cloud Gate metal artwork is the centerpiece of Chicago’s Millennium Park. It acts like a warped mirror that bends the surrounding skyscrapers in its view. Immerse yourself into the mob of selfie sticks and tourists to get a cool view of the city through the Cloud Gate. You can even walk under it!

Coffee at Chicago Tribune Tower
The Chicago Tribune Tower is the quintessential symbol of old Chicago. Its 1920-esque neo-gothic towers and spires harken back to the glory of old newspapers. Enter into its lower level and grab a coffee at one of its local (or chain) coffee shops.

Navy Pier
The 100-year-old tourist attraction is more of a mall than a functioning pier, but it’s fun nonetheless. Stroll along the shores of Lake Michigan, get beaten down by the chilly wind, and watch the Ferris Wheel spin methodically while you enjoy any one of the chain restaurants within the pier’s building.

Magnificent Mile
This alliterative area contains towering skyscrapers, designer shops, and some of the best people watching in the country. It’s the heart of downtown Chicago. You’ll experience old churches, 1920s buildings, and window shopping until you reach the end of the road.

Intelligentsia Coffee in Old Town
Stroll into Old Town Chicago to this hipster coffee shop the echos Portland’s local cafe scene. Old Town has recently received a total renovation, and this coffee shop is the posterchild for new Old Town. Plus, they make a phenomenal cappuccino and have incredible music (Chance the Rapper’s entire Coloring Book album played during my stop).

Orso’s Italian Restaurant in Old Town
The last great remaining restaurant in Old Town, Orso’s has been family-owned and unchanged since the 1960s. Their angel hair pasta is incredible, their tap selection illuminates Chicago’s craft brew scene, and their house-made lemoncello will leave you loving Orso’s. Ask the bartender about what Orso’s remembers from Old Town’s shady past; apparently Wells Street was Chicago’s Red Light District in the 60s and 70s.

Wrigley Field
This legendary Chicago stadium has gained an even greater ambiance after the Cubs’ 2016 World Series victory. Simply exploring the surrounding Wrigleyville area gives you sense of the dedication that Cubs fans have for their home team. Check out the pubs the line the stadiums bordering streets. Even the Wrigleyville Starbucks is cool (built inside an old theater).

Biograph Theater
John Dillinger earned the title of Public Enemy Number One in 1934 after robbing over 24 banks. On July 22, 1934, he headed to the Biograph Theater with a red-headed date, who dimed him out to the fuzz. When he left the theater, he was shot dead in the street by the F.B.I. The theater still operates as it did in 1934, minus Public Enemy Number One.

St. Valentine’s Day Massacre Site
In 1929, Al Capone was competing for total control of the bootlegging industry in Chicago against his prime adversary, Bugs Moran. On February 14th, 1929, Capone sent hitmen dressed as cops into Moran’s headquarters and massacred the entire crew, which crippled Moran’s operation. Though the building has since been torn down, the site still remains as a lone grass field. Visit the antique shop next door for some authentic photos of the police investigation.

Chicago Pizza and Oven Grinder
Rumor has it that Capone’s guys waited at this location across the street from Moran’s headquarters to scout the scene before the St. Valentine’s Day Massacre. Nowadays, this restaurant serves this incredible concoction called a “Pizza Pot Pie” that’s just as filling and awesome as it sounds.

Halligan Bar
Formerly owned by Bugs Moran himself, this Irish bar sits at the apex of a triangular street corner. The modern bar has only been in operation since 2001, but the history of the building is worth the stop.

I’m sure I missed countless awesome stops and sights during my Windy City adventure, but the spots I found were incredible and provided me with a solid understanding of Chicago. Let us know where to visit during our next stay in the city!

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Tom Malone is the Editor-In-Chief of The Adventure Tribune and author of adventure novels, like Across Americana. He is based in Denver, Colorado, where he adventures through the Rocky Mountains while not traveling abroad.
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