Hyde Park

All my flights from the East to Chicago end this way. After an indifferent run across uniform southern Michigan farmland, we burst upon the blue expanse of Lake Michigan, momentarily as big as any sea one must cross to get to a place completely unknown. Then the pilot comes on the intercom: we’re descending, we’re arriving soon, the wind is windy, the Cubs are losing, have a good day. Some passengers moan and wonder: descent? did he say descent? Good God we’re over water. I thought we were going to Chicago.

While they shift and lurch and try to remember the instructions half-heard two hours before about flotation devices, I ease back and almost say out loud: the Lake looks good to me. A hit of the Lake before landing in the prairie’s drift and then driving into the humid heft of the city is just what I need. I romanticize the Lake. Even though I know and even dream the tales of the Lake’s dangers—ore ships vanishing, nice people like my fourth-grade teacher drowning—I still want to be out there, nudging through the Lake’s waves. Riding to nowhere with my dad in Dr. Calloway’s powerboat at six in the morning with only a sack of chocolate donuts for breakfast and only a thin White Sox jacket to shell off the fog and breeze—that’s where I want to be. Riding the ferry from Milwaukee to Ludington on a sunny childhood day, playing shuffleboard during the few intervals the ship’s captain doesn’t need my helmsmanship—that’s not bad, either. Aching with hope that the one man in my father’s crowd with a sailboat, a fast yawl no less, might ask me to help crew in the next Chicago to Mackinac race—that’s a first-rate might have been, an outstanding almost happened.

But then we land and it’s time to get down to business, the business of getting out to the South Side. Years ago, provided that I wasn’t traveling with my wife—who is deeply suspicious of my homegrown itineraries—I’d plan elaborate schemes of travel, with transfers, double-transfers and the like. It was just no fun and much too adult simply to hail a cab and debark at home forty-five minutes later. I’d claim that I couldn’t afford a cab, but what I really couldn’t afford was depriving myself of a short wade into the city’s essences.

These days, I grab a cab more and more, chiefly because the cabdrivers are more interesting. Gone, it seems, are the sullen rednecks who resent driving you anywhere; gone, too, are the tiresome black cabbies who want to know “how many coloreds are up to that college you go to?” or want to borrow ten dollars—“I know your address and everything, you know I’ll pay you back.” No, these days you get the West Indian and East Indian and even West African types: brothers with cabs like living rooms, smelling like sweet flowers, decked out with photographs, doilies, little national flags and no smoking signs in three languages. These brothers have coolers with sodas and iced cappuccinos; when they offer a cold drink they add, “Would you like my business card, too?” I like these dudes because they make you think uplift and hustle are still the order of the day. But these guys are new to Chicago. There’s another reality, too, dancing not to the hustle but to the blues.

The “blues ride,” the “nachal” ride full of testiness and style and eruptions of funk, comes not in the rolling parlors of the new American dreamers but instead in the utilitarian vans of the A2B Coach Company, a black-owned outfit that serves the University of Chicago by way of stopping half a dozen places where blackfolks might want to go. There’s a published route with designated times, but like a Gershwin tune that’s caught the eye of Sonny Rollins, it’s a score about to be improvised upon. Frankly, I...