The longest route in the Chicago Transit Authority’s bus system is the #9 Ashland, which runs 16 miles between Lake View, on the mid-North Side, and Washington Heights, on the Far South Side. I can’t imagine many people travel between those neighborhoods, but if they do, there’s no transfer.

I ride the bus a lot, but I had never ridden a bus that far. As a regular CTA passenger, I want to get the most bang for my buck. At a $2.25 fare, the #9 costs 14 cents a mile. Beat that, Uber!

And so, on a cold February morning, I leave home early, carrying a bag containing everything I need for my epic ride: a peanut butter and jelly sandwich, an apple, a bag of granola, a paperback novel, a transistor radio with headphones, a notebook, a pen, and an extra pair of mittens. In my pocket, I have a box of matches, which will come in handy if I need to start a fire to keep warm while waiting for a bus.

I never need the matches. The first thing you need to know about the #9 is that it’s reliable. Unlike most of the CTA, which leaves riders waiting as hopelessly for the next bus as Vladimir and Estragon waited for Godot. To get to the #9, I wait 25 minutes for a #22 Clark bus in Rogers Park. (Actually, I don’t wait. I walk to Andersonville and catch up with the bus there.) But I board the #9 at Ashland and Irving Park, catty corner from Lake View High School, after standing three minutes in a bus shelter. That’s the service one expects from a flagship bus route.

At 10:10 in the morning, there is only one other passenger, a young woman with pink-streaked hair and platform boots. She gets off at Fullerton, long before Washington Heights. Here are a few notes from early in the ride, which I type into my phone — because it turns out I forgot the notebook:

  • Belmont/Ashland/Lincoln 6 corners
  • Dry cleaners, diners, Jewel strip mall
  • 21st Century brick condos
  • Crosses Chicago River. Bridge w/ WPA design
  • Under Bloomingdale Trail
  • Man in a leather hat w sunglasses on brim talking on phone. Can’t understand what he’s saying. Sounds like Willie Wilson.
  • Mike’s Furniture. Sale sale sale.

A ride on the #9 bus is a sociological, as well as a geographical journey, because it passes through every economic strata of Chicago, from upper, to middle, to lower, then back to middle again. Here is a list of all the community areas the bus serves, and their median household incomes.

  • Lake View: $92,779
  • Lincoln Park: $115,389
  • West Town: $104,639
  • Near West Side: $73,586
  • Lower West Side: $66,414
  • McKinley Park: $61,814
  • New City: $43,834
  • West Englewood: $26,598
  • Auburn-Gresham: $37,484
  • Washington Heights: $69,782

South of 42nd Street, the #9 is far more crowded than it is in Lake View, even though the neighborhoods are far less populous, because a much larger proportion of the residents depends on public transportation. At 47th Street, a man lugs a shopping cart onto the bus, stuffed with plastic bags full of groceries from Dollar Tree. Some impressions from the second half of the ride:

  • Subway, Oxford Insurance, Domino’s
  • Open 7 Days. 57th Supermarket. We never close. Closed.
  • Gas stations, empty lots, restaurants with rusted gates
  • Day care center
  • Revival Tabernacle
  • Harold’s The Fried Chicken King, 69th Street. Sign: man chasing chicken with ax
  • Walmart at 76th
  • Ghost sign for Elmo’s Tombstones: Made While U Wait.
  • Phone convo: “She shouldn’t be bringin’ this shit.” “I ain’t out here fucking.” “She buggin’.”

The bus lets me off at 95th Street, which is a little disappointing, because the CTA map promised a ride to 104th Street. According to a sign, service is “Extended south to Vincennes/104th Weekdays, AM rush period and early afternoon thru PM rush period.” It’s 11:41 a.m., an hour and a half after my ride began in Lake View, so I’m in that dead zone.

“Is there a bus to 104th?” I ask the driver of the next bus.

“There should be one more,” he says. “They come in increments. It could be another 20 minutes.”

For the next 20 minutes, I stand on the corner of 95th and Ashland, eating from my bag of granola. Three more 95th Street buses arrive, but no 104th. I decide to walk the rest of the route. Ashland Avenue comes to an end at 95th Street, so I follow Beverly Boulevard to the end of the line, near Percy Julian High School.

On my way back to the bus stop, I discover the best reason for riding the #9 all the way to its terminus: Poppin Dough, a popcorn and doughnut stand at 1235 W. 95th St. Poppin Dough is the newest of the great South Side doughnut joints. There’s a good reason for that. When founder Richard Gray decided to quit his job as a therapeutic crisis interventionist and go into the doughnut business, he approached Burritt Bulloch, owner of Old Fashioned Donuts in Roseland, and asked if he could spend some time working in his shop and learning from a master. Bulloch agreed to show him how to do doughnuts right. 

“This building has been in my family for 50 years,” Gray says of his hut-sized brick storefront. “I got it from my grandfather. My oldest son was a barber, so I opened a barbershop here. He decided to move to 47th Street, closer to the city. My wife said, ‘I know you’re tired. How about opening up a doughnut shop? I can do popcorn. There’s no combination of that in the city.’”

Gray has too much respect for Bulloch to claim his doughnuts are as good as Old Fashioned’s — “he’s got 40 years of experience, so I’m not much competition, but I make a pretty good apple fritter, too. I make pretty good cake donuts: butter pecan, strawberry, lemon. This is actual cake donuts, not icing.”

Gray does, however, claim that his wife, Phyllis, makes “the best popcorn in the state. If you look at our reviews, you will see people say we make popcorn better than Garrett’s. We make buffalo ranch, green apple, Guadalajara, cheesy caramel — that’s cheese and caramel in one kernel, not a mix.”

I buy a bag of doughnut holes — blueberry, cinnamon, cake — and nosh on the half-mile walk back to Ashland, where I don’t have to wait long for a northbound bus. Just long enough to eat my apple. As well supplied as I am, I have neglected to bring along my portable phone charger, so I debark in Back of the Yards and replenish my 8% power phone from a wall socket at El Cabrito, a 47th Street taqueria, while lunching on an avocado torta.

On the ride back to Lake View, the #9 bus’s demographics change dramatically in just a few blocks. At 18th Street, in Pilsen, all the passengers are Latino (except me, the guy listening to WXRT on his headphones). North of Roosevelt Road, most of the passengers (including me) are white. Beyond Diversey, the bus is nearly empty (except for me). The journey ends at Clark Street and Belle Plaine Avenue, outside the brick wall of Graceland Cemetery, where I have to wait a long time for a #22 bus home. Standing in the cold, I shake the box of matches in my pocket and look for a trash can. I miss the good old #9, a bus that’s always there when you need it.