As I navigated the minefield of growing up Black in America, I leaned on Digable Planets, a ’90s hip-hop trio that rapped about Black existence through the prism of New York’s boroughs.

Digable Planets, who mined jazz and funk for samples, remain relevant, especially in a world where a race-baiting demagogue can win the nomination of a major political party.

When I learned the group was reuniting, I knew I had to see them live for the first time. To get the most bang for my travel buck, I booked tickets for the second day of the Pitchfork Music Festival, a three-day event in Chicago’s Union Park.

The Windy City wasn’t windy the last time I visited. In fact, the weather was inhospitable, with temperatures hovering north of 100 degrees for the few days I was there in July 2011. For that trip, I was there for Pitchfork and to help a friend relocate to Washington, D.C.

If you follow the news, especially on holiday weekends, you’d think all of Chicago was a battleground, with dead bodies in the streets, covered by white cloth, more common than potholes.

“Be careful in Chiraq,” my mom texted, referring to the city’s nickname.

For this trip, I was joined by my colleague, Sue, who lives in Queens. She had never been to the surprisingly inexpensive city. Here are highlights from our three-day visit.


One of the reasons I prefer Airbnb to hotels is that it’s cheaper in larger cities. I also like staying at homes so I can immerse myself into the local neighborhood. Airbnb has come under fire for race discrimination (, and in recent months I’ve had booking requests accepted, and then suspiciously denied. Our hosts restored my Airbnb loyalty. We settled on The Roosevelt Suite ( in Little Village, because it was within a block of public transportation, it looked cool and it was within our $600 budget. Some reviewers on Yelp and Reddit claimed the neighborhood was sketchy. We found out that was code for “mostly people of color live there.”

Our hosts, who were white, answered a request for dining recommendations with links and maps with arrows. They also provided detailed directions from the airport. The suite, with exposed brick and beams, was a study in studio design. The kitchen had a table and decorative gold pots and skillets. Sue made us tea in the morning as we ate cranberries and granola, all provided for us.

Our hosts live upstairs. We ended up sharing life stories with one of them. The smell of food frequently wafted into our space. Dogs had the same kind of freedom, too.


The Airbnb came with bikes. Sue’s was too big for her. No problem. There was another for her to use. Biking was arguably the best part of our trip. We left in the morning on the way to the festival, stopping first at the 16th Street murals, many of which are wrapped around train platforms in University Village and Pilsen, the historically immigrant neighborhood that is now mostly Latino. We ate at Nana’s, where the deep-fried avocado with chipotle-lime aioli is popular—and delicious.

Because Digable Planets didn’t go on until after 3 p.m., we decided to meander through the Canaryville, Grand Boulevard and Kenwood neighborhoods

We rode on 47th Street through the northern most tip of the South Side, where much of the city’s violence is concentrated. But if you’re not marked opposition in Chiraq, you’re cool.

At Lake Michigan, with the skyline to our left, we paused to enjoy the view as a cool air blew in rhythm with the water lapping the concrete at our feet.


The festival, after all, wasn’t the place for a die-hard head to see Digable Planets. It wasn’t intimate enough. I’ll see them this month in San Francisco. BJ the Chicago Kid, Anderson. Paak, Blood Orange, Sufjan Stevens and Savages were our festival favorites. Serendipitously, I met Butterfly, one-third of Digable Planets, at a pizza joint later in the evening. The pie was a terrible representation of Chicago deep dish. On our final night, Chicago pizza was redeemed by Guerrero’s, which is around the corner from our Airbnb.


Chicago’s public transportation, with miles of above-ground tracks, is a wonderful way to see the city. It only costs $3 to ride anywhere because the system isn’t metered. You can clearly hear stop announcements and signage is decipherable. Our Airbnb was visible from the California stop on the Pink Line.


The smell of stale beer and the sounds of weekend-night karaoke permeated. Yeah, horrible. Good thing for us, we were in the area to see Horrible Fun’s interactive improv comedy at Under the Gun Theater. Actors created scenes with finger-snapping wit after the audience completed bawdy sentences using a Cards Against Humanity deck.


I wanted to see “Invisible Man: Gordon Parks and Ralph Ellison in Harlem” at the Art Institute of Chicago. The exhibition details two projects that Ellison, a writer, and Parks, a photographer, collaborated on. It was a fascinating and inspiring look at the work of two pioneers.

We also enjoyed Claude Monet’s “Stacks of Wheat” series and “A Lot of Sorrow,” the collaboration between Ragnar Kjartansson and The National, a video of The National playing its song “Sorrow” for more than six hours.

Before the museum, we walked through Maggie Daley Park, and then on the Frank Gehry-designed BP Pedestrian Bridge, the winding path constructed of sheet metal and aluminum that connects Daley Park to Millennium Park.

We ate lunch on a bench underneath trees as Pokemon Go players bumped into each other. Then we joined the crowd at Cloud Gate, a 110-ton elliptical sculpture that beckons you to stare into its mirrored surface.

I can see myself not waiting long to visit Chicago again.

Otis R. Taylor Jr. is a culture writer with a battle rap obsession. He is based in Oakland, Calif., and is the managing editor of