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Chicago After Dark

Stranger Files by Stranger Files
January 18, 2026
in Rideshare
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red car on road during night time

Photo by Slava Arkhipenko on Unsplash

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I was driving for Uber on a chilly night in the fall of 2023, the kind of Chicago evening where the cold wind seemed to slice through even with the heater running. I’d already logged a few hours, and my plan was to wrap up after one or two more rides.

That’s when I got the ping.

The pickup was outside a bar, which was never a good sign. I told myself it would be fine—five stars if I kept it smooth, maybe even a decent tip.

When the guy stumbled toward my car, I knew I’d made a mistake. His clothes hung sloppy on him, his eyes glassy, and the moment he collapsed into the back seat, I caught the heavy stench of liquor.

His words slurred together, not in sentences but in demands. He wanted me to stop at a liquor store before heading to his destination.

I’d been through this before. Company policy was clear: no stops like that, especially when someone was already in bad shape. I tried to stay calm, acting polite, but I let him know it wasn’t an option. That’s when his tone changed.

At first, it was muttering, the kind you pretend not to hear. Then it became louder, angrier. He started pounding the back of my seat, calling me every name in the book without actually saying it straight.

The car felt smaller with every second, the tension building like static electricity before a storm.

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Chicago streets are unforgiving at night. Traffic lights feel longer, side roads darker, and every corner is a blind spot. As I kept driving, I couldn’t help but glance in the rearview mirror.

His face had gone hard, jaw clenched, hands twitching on his knees. I kept both hands on the wheel, heart racing, wishing I’d ignored that ride request.

He leaned forward suddenly, close enough that I could feel his breath on my neck. He kept insisting I pull into the next corner store. I stayed steady, eyes locked on the road, repeating in my head that I just needed to get him to the drop-off and be done with it.

But the way he shifted in the seat, the way he gripped the headrest like he was about to launch himself forward, told me this wasn’t going to be easy.

The streets grew emptier the further we went. His voice dropped into something low, almost threatening. He kept telling me how stupid I was for not listening, how people like me ended up regretting things.

My knuckles whitened around the steering wheel, and every block felt like a mile.

At a red light, he slammed his fist against the window hard enough that I thought the glass might crack. My instinct screamed at me to get out, to walk away from my own car, but I stayed put. Leaving would’ve meant abandoning myself in the middle of Chicago at night with him still inside.

When the light finally turned green, I hit the gas too hard, tires squealing as we lurched forward. He laughed at that, a sound that felt more unhinged than drunk, like he was enjoying the control he thought he had over me. We were close to the destination, and I told myself to hold on.

But then he lunged forward, grabbing at my shoulder. The car swerved toward the curb, and I yanked the wheel back just in time to avoid hitting a parked car. My heart was pounding so loud I could barely hear anything else.

I pulled into his street faster than I should have, barely slowing before I reached the address. I threw the car into park and told him, without words, that this was the end of the line. He sat there for a long moment, eyes fixed on me in the mirror. I couldn’t read if he was going to lash out or laugh again.

Finally, he shoved the door open, staggered into the night, and disappeared down the sidewalk. I sat there shaking, doors locked, engine running, trying to process what had just happened. It was supposed to be just another ride, another night of extra cash.

But in that moment, I realized how thin the line really is between being in control and being at the mercy of a stranger in the back seat.

This whole ordeal was enough, for me to call it a night.

Tags: RideshareUber
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Stranger Files is a curated collection of fictional horror narratives inspired by chilling real-world encounters and unexplained phenomena.

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