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Walk a Mile on Division Street

Posted on January 29, 2025   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Hey Chicago newsletter editor in front of a Humboldt Park sign

Did I play the new Bad Bunny album while I walked along Division and pretended I was in Puerto Rico? Yes, yes I did. (Sidney Madden / City Cast Chicago)

Division Street Revisited” is a new podcast revisiting seven of the original subjects in Studs Terkel’s 1967 oral history that chronicled the lives of Chicagoans in the 20th century.

While there is a Division Street in Chicago, Terkel said the title of his book was mostly a metaphor. But that didn’t stop this newsletter editor from walking Paseo Boricua and beyond in Humboldt Park.

City Cast

Puerto Rican and Latinx Culture Thrives in Humboldt Park and Hermosa

00:00:00

How it Works

  1. We pick an area within city limits.
  2. We pick a mile to walk (on Division Street between Humboldt and Campbell).
  3. We recommend ~10 things to do in that mile.

How to Get There

  • Bus No. 70 along Division Street; Nos. 49 and 52 buses to Division
  • Divvy at California and Division
  • Blue Line to Western or Metra to Western
Google Map of a stretch of Division Street

A few stops along Division Street. (Google Maps)

What to Do

Start your walk at the free National Museum of Puerto Rican Art & Culture. Explore exhibits on queer local Boricua artists and Three Kings Day. Or go on a docent-led tour, which usually happens mid-month.

Walking through the neighborhood’s namesake park is always nice, but I prefer to go in the summer when you can swim in the city’s only inland beach or pedal on a swan boat through the lagoon.

I am not a gym girly, but if I lived closer to the newly opened Humboldt Park Wellness Center, I would gladly become a member at the three-story, 45,000-square-foot facility. That Olympic–sized swimming pool makes me want to find my high school swim team cap and do a few laps.

This is the stretch of the walk where I felt like the main character in a movie. I got my little treats at Cafe Colao — a guava-filled puff pastry and passionfruit lemonade — and then picked up a bouquet at Flores Del Amor to add some green to these dark Chicago winter days.

The AfriCaribe Cultural Center has dance and drum classes starting this week and next. Add it to our long list of art and music classes in the city!

Pictures of the Paseo Boricua flags, Cafe Colao, Flores Del Amor, the National Museum of Puerto Rican Art & Culture, and AfriCaribe Cultural Center

On a stroll along Division Street, you can stop at the Paseo Boricua flags, Cafe Colao, Flores Del Amor, the National Museum of Puerto Rican Art & Culture, and AfriCaribe Cultural Center. (Sidney Madden / City Cast Chicago)

In the mood for breakfast? Nellie’s is the place to be. The family-owned restaurant’s coconut oatmeal is so popular they sell it by the gallon.

The humble jibarito sometimes gets forgotten in Chicago food lore. But order the juicy steak sandwich smashed between fried plantains from Papa's Cache Sabroso, and you’ll see why it’s one of the best in the city.

City Cast

How the Jibarito Became a Chicago Icon

00:00:00

Pretend you’re somewhere tropical at Esmeralda’s Lounge, where Patron shots are $4.50 on Wednesdays.

Want to end your walk with unique shopping? Peruse religious figurines at Botanica Victoria and wellness products at Alkaline Healing Herbs.

🚶 More walking guides!

“Division Street Revisited” is having a launch party at the Harold Washington Library tonight. Episodes are dropping weekly through March 21.

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