Driver story: the night I drove 300 miles for $40

How it started

It was a Friday in late January, 11:40 p.m., and I was in Joliet, Illinois, 35 miles southwest of downtown Chicago. I'd driven down for a relative's birthday dinner, and on the way back I figured I'd turn on the apps and pick up a few fares to cover gas. The night was clear, the temperature was 19°F, and I had a full tank. What follows is the worst shift of my three-year rideshare career, told in approximate real time.

At 11:42, a long-distance Uber trip popped: a passenger at a hotel in Joliet needed to get to O'Hare. The fare was showing $87. I'd never had a $87 trip. I accepted immediately. The pickup was 4 minutes away. This is where the problems started, though I didn't know it yet.

The pickup

The passenger — I'll call him D — came out of the hotel at 11:51. He was apologetic and a little frantic. His flight was at 1:55 a.m. (red-eye to the West Coast), and he'd booked a later Uber that had cancelled on him. He offered me $20 cash to drive fast. I told him I'd drive safely and we'd make it. O'Hare from Joliet is 38 miles, GPS said 47 minutes. We had two hours. Plenty of time.

We hit I-80 east at 11:54. Traffic was light. At 12:18, just past Cicero, the car started shuddering. I'd been getting a check-engine light intermittently for two weeks and ignoring it. The light came on solid and the shuddering got worse. I pulled onto the shoulder. D was very calm, which I appreciated.

The breakdown

It was a misfire — I'd later learn a fouled coil pack. The car would limp at 35 mph but not faster. D's flight was in 95 minutes. We were 22 miles from O'Hare. At 35 mph, that's 38 minutes — possible, but tight. I told D I'd get him there but he should rebook if he had travel insurance. He decided to ride it out.

From 12:25 to 1:05, I limped north on I-294 at 35-40 mph, hazards on, getting passed by every car on the road. D was on his phone rebooking his flight. At 1:07, two miles from the airport, the car died completely. The alternator had given up — the battery, drained by the misfiring engine, finally quit. We coasted to a stop on the shoulder of I-190, the airport entrance ramp visible ahead.

Two miles from O'Hare, 48 minutes before his flight, the car died. We were so close the airport lights lit up the cab. I have never felt more stupid in my life.

The last two miles

D looked at me. I looked at him. He said, 'Can we walk?' It was 19°F, the highway shoulder was icy, and walking on I-190 is technically a felony. He called 911 to ask if a passenger could walk to the terminal from the highway. They told him no and sent a state trooper. The trooper arrived in 8 minutes, was unsympathetic but practical, and drove D to the terminal. D made his flight with 22 minutes to spare. He handed me the $20 he'd promised, plus another $20, and said 'I hope your car gets fixed.' Then he was gone.

I sat in the dead car on the shoulder at 1:25 a.m. waiting for the tow truck I'd called. The fare, because the trip hadn't completed in the app, was zero. Uber had already charged D a cancellation fee (later refunded). I'd driven 47 miles and earned $40 in cash, and now I was looking at a $310 tow bill and a $480 repair. Net for the night: -$750.

The three rules I now follow

That night produced three rules that have prevented any repeat in the 18 months since. First, the check-engine light means something. I'd been ignoring it because the car seemed fine. Cars are not 'seemingly fine' when their computers are warning you. Now any check-engine light means a mechanic visit within 48 hours, no exceptions. The $180 diagnostic would have caught the coil pack before it stranded a passenger.

Second, never accept a long-distance trip without confirming the car is road-trip ready. I now do a 60-second pre-flight check before any trip longer than 30 miles: tire pressure, oil light, check-engine, fuel level, lights, wipers. Sounds paranoid; takes 60 seconds; has caught two issues I'd otherwise have driven on.

Third, carry a roadside kit and a charged power bank. The kit: jumper cables, a basic tool roll, a flashlight, a blanket, water. Total cost: $60. The power bank: I'd let mine die. D's phone was at 12% when the trooper arrived, and if the trooper had been 20 minutes later, he'd have been stranded without a way to call anyone. The $40 I now spend on a power bank I keep charged is the cheapest insurance I own.

What I'd do differently, in hindsight

Three smaller things. I'd have declined the trip. Not because long trips are bad — they're great when the car is healthy — but because I'd ignored the check-engine light for two weeks, and accepting a 38-mile airport run in a car I knew was misbehaving was the kind of optimistic stupidity that ends in -$750 nights. The car told me it was sick; I didn't listen.

I'd have called a tow truck the moment the car started shuddering, not 30 minutes later when it died. Hauling a misfiring car 22 miles at 35 mph on I-294 was dangerous and made the alternator failure worse (the misfiring engine overworks the alternator, which is why the battery died). A $150 tow from Cicero would have cost less than the $310 tow from I-190 plus the additional engine damage from limping it.

I'd have communicated more with D. He was a good passenger — calm, helpful, didn't blame me. I could have made it easier by being upfront: 'I think my car is failing; here are our options; here's what I recommend.' Instead I pretended I had it handled while driving 35 mph on a highway, which must have been nerve-wracking for him. Drivers owe passengers honesty about car problems, even when it's embarrassing.

The coda

Two months later, D booked me again. I didn't recognize him until he got in the car. He recognized me. We laughed about it. He told me he'd made his flight, his meeting had gone well, and he'd been telling the story of the 'rideshare driver whose car died two miles from O'Hare' at dinners for months. He tipped $30 on a $22 fare. The rideshare world is small, and the passengers who see you at your worst sometimes remember you at your best.

I still drive. The car got fixed, I bought a dashcam the next week, and the three rules have held. But on cold January nights when the apps ping with long airport trips, I think about that night on the shoulder of I-190, the airport lights so close, and I check the engine light before I accept. Some lessons cost $750. This one was worth it.