Wintrust Financial

About this location

A few stories people tell about this place

1. One morning, a delivery driver pulled up to Wintrust Financial with a puzzled look on his face. Over the intercom came an unfamiliar voice: 'Please leave your package here and take a number. Your transaction will be processed in exactly twenty-seven minutes.' The delivery driver shrugged and left the package. Twenty-seven minutes later, he was still waiting. Finally, a bored-looking teller handed him a cup of coffee and said, ‘Your transaction’s been processed—you’re now overdrawn by $27.’ Everyone in the neighborhood started calling it ‘Win-Twenty-Seven,’ and the bank became famous for its unique customer service.

2. Late one night, a security guard patrolling Wintrust Financial heard an odd humming sound coming from inside the building. Curious but cautious, he approached the source only to discover rows of computers quietly playing the same old-time radio jingle over and over again. As he watched in amazement, the guard realized that each computer was tuned to a different decade’s classic station. Just as he was about to investigate further, his walkie-talkie crackled with a voice asking if everything was okay. Turning around, he saw only empty corridors—except for one smiling face on a screen, saying, ‘It’s just us old-timers catching up on some nostalgia.’

3. In the early hours of dawn, a jogger passing by Wintrust Financial noticed something peculiar—a faint scent of freshly baked cookies wafting from the building. Curious, she peered inside and saw nothing but empty desks and quiet hallways. Suddenly, a voice called out from behind her: 'Cookies are for customers only!' Startled, she turned around to see an elderly teller smiling warmly. The legend lives on—Wintrust Financial’s secret cookie stash is strictly confidential.

4. Have you ever seen a bank teller handing out free cookies? That's what some customers started noticing at Wintrust Financial. It turned out that every Tuesday afternoon, one of the bank’s employees brought in freshly baked cookies for her colleagues—and sometimes shared them with delighted customers waiting in line. Soon enough, Wintrust became known as ‘the cookie bank,’ and everyone wondered if their good fortune would run out. But nope—cookies kept appearing like clockwork until someone finally asked where they came from. Turns out, it was just an enthusiastic baker next door who thought spreading joy was worth a little extra effort.