The distinction is part of an annual roundup of facial hair-friendly cities in America by men's grooming company Wahl.
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Chicago narrowly missed the top honor last year to Philadelphia.
But this year, the Windy City intercepted for the win with help from Trubisky.
He made a beard pact with the rest of the Chicago Bears' quarterbacks in last year's postseason.
"I had faith we would make it to the playoffs, so I started my playoff beard a little early and it paid off." Trubisky said. "While some guys grow beards to intimidate, for me it was about exuding confidence."
To celebrate Chicago's win, Wahl is kicking off its national Facial Hair Friendly Cities tour at the Bears100 Celebration Weekend June 8-9, 2019 in Rosemont.
In addition to offering free mustache and beard trims, Wahl will host Trubisky at their 30-foot mobile barbershop from 1 p.m. - 2p.m. on Saturday, June 8.
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Trubisky is expected to take his turn in the barber chair for a touch up, and engage with fans in some fun facial hair activities.
2019 Top 20 Most Facial Hair Friendly Cities:
1. Chicago
2. Atlanta
3. San Francisco
4. Los Angeles
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5. Seattle
6. Portland
7. Austin
8. New York
9. San Diego
10. Philadelphia