Eighteen hours after departing Washington, DC, Amtrak’s Capitol Limited pulled into Chicago’s Union Station. The 36 passengers, all riders on the Passport Express, were eager and excited to disembark and explore. With much of the day free, those most familiar with the city offered to lead folks around, taking them to their favorite local spots.

The Passport Express arrives in Chicago

Here, Chicago-native Fran Tirado details his group’s afternoon of exploration through the dynamic neighborhood of Wicker Park.

Imagine this: you’ve lived in Chicago for much of your life. The Windy City, as it’s known, is a part of your heart in the corniest way possible. You love everything about it—the architecture, the smiling neighborhood store owners, the elevated subway known as the ‘El,’ the pizza. You even love the wind.

Now imagine pulling up to Chicago on a train after being gone for a whole year. You’ve traveled there with some of the most inspired people you’ve ever met, many of whom you’ve only known for 24 hours. After a group brunch at a restaurant downtown, Gage, you’re told that you have the rest of the day free.

What would you do?

In the midst of all the developing plans, I spoke up and suggested to my fellow Passport Express riders they come on a tour to see some of my favorite parts of the city—my Chicago. My recommendation was to begin in the neighborhood of Wicker Park.

Some might say that Wicker Park is to Chicago as Williamsburg is to New York—a rising neighborhood with neatly-branded coffee shops, artisan hat stores, and hipsters on bicycles. It is all of those things, sure, but it is also so much more. In the 1850s, Wicker Park was a district of makers. Just outside the downtown Loop, those who lived there made clothes, musical instruments, cigars, furniture, and beer. Ironically, now 2015, the neighborhood still serves a similar purpose. It’s a hub of artists who manufacture art in their own right: brass jewelry, fine espresso, used books, rare records, and yes, more beer.

We started at the Wicker Park Secret Agent Supply Co., a place that’s almost exactly what it sounds like. The store sells disguise mustaches and X-ray goggles, and is also a non-profit organization that offers creative writing programs for kids for free. They even sell the students’ published writing. We browsed through the items and bought gifts, feeling uplifted.

Photo Credit: Roxana Moussavian (top right), Zach Glassman (bottom)

We strolled down Milwaukee Avenue and considered getting corazones— heart-shaped, sugar-covered, melt-in-your-mouth cookies that I enjoyed all throughout my childhood. They’re a popular item at Artemio’s bakery, a well-kept Chicago secret, but we opted for La Colombe coffee and donuts instead. As we chatted and wandered together, we decided to challenge ourselves with a creative assignment: to take a photo or write or draw something that wouldn’t normally be part of our typical work. We dispersed a bit as we took on that challenge, all of us committing ourselves to it without pressure or strain.

Photo Credit: Mat Rick


We reconvened by the fountain in Wicker Park’s actual park as the sun started to set. We shared photos of curly-haired silhouettes and laughing portraits in fire escapes, feeling proactive about our work. Hungry, we decided on one last stop for the day – tacos at the now infamous Big Star. As we all sat down with our taco baskets and hot bags of chips, I felt quite full, both physically and mentally. Chicago is a beautiful place, yet understated all the same. I know it well, but there are always new corners to discover. I couldn’t think of better people to share and explore my favorite city with than new friends who challenged me to view a place I’ve known my whole life in a completely different way.


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The Passport Express