Enterprise

About this location

A few stories people tell about this place

1. In the early hours of every Friday morning, a delivery driver pulled up to Enterprise Rent-A-Car in downtown Chicago. As he approached the counter, the clerk would always notice something peculiar: the driver’s rental agreement had been signed with a tiny pencil sketch of a unicorn. Finally, after months of speculation, it turned out that the unicorn was simply an elaborate doodle made by a regular who drew them everywhere—even on his coffee cups and grocery lists. The manager smiled knowingly as he said, ‘Welcome back, Mr. Unicorn.’

2. In the dim light of an early-morning breakroom, a delivery driver noticed something odd in the refrigerator. A bottle labeled ‘Enterprise Special Reserve’ stood out among the usual coffee and water. Nobody remembered ordering it. Curious, he opened it—only to discover a vintage bottle of ketchup with a handwritten note: ‘For your next road trip!’ Turns out, someone’s idea of a prank had everyone talking for weeks.

3. At dawn, when most gas stations are still locking their doors, a delivery driver approached Enterprise Rent-A-Car. The parking lot was empty except for one familiar silhouette—an old neighbor who always parked there late at night. The delivery driver waved and said, ‘Morning, Joe!’ The neighbor smiled back sheepishly, adjusting his cap. Turns out he’d been sleeping in the car since last night’s storm knocked out power at home. As they chatted, a security guard drove up, asking if everything was okay. Joe explained with a laugh, ‘Just catching some zzz’s here, officer.’ The guard nodded knowingly, shaking his head and muttering under his breath, ‘Another regular’.

4. At 3 AM on Sunday nights, a delivery driver approached Enterprise Rent-A-Car and heard an eerie announcement over the intercom: ‘If you see a customer with a unicorn-shaped keychain, please inform them it’s ours.’ The next morning, the delivery driver found himself in line at the coffee shop across from Enterprise. A familiar face waved him over—an older gentleman who’d been there every Monday for years. The man whispered, ‘I saw your little adventure last night. Nice work!’ Turning around, the driver noticed everyone else smiling knowingly too. From then on, whenever someone spotted a unicorn keychain, they’d discreetly nod—a secret club of good samaritans.