Perhaps best known as the home base of the Daly dynasty (you know, the American Pharaohs), Bridgeport is a small and eclectic neighborhood on the near South Side (though it’s only an 8 minute drive from Hyde Park, it takes about an hour to get there via public transit. Trust me. I know). For one reason or another, its residents fiercely defend the distinctiveness of the neighborhood. The local Assembly of God has gone as far as to make their own custom “Bridgeportopoly” which you can buy or win as a prize at Bernice’s Tavern (see below).
One thing is for sure: Bridgeport is home to what some would call the best coffee in the city, to be found at Bridgeport Coffee Company. Check it out early on a Wednesday night and then head over to the beating heart of the neighborhood (remember, it’s a small neighborhood) to Halsted Street. There, you’ll find Bernice’s Tavern, a gem of a dive bar owned by Mike and Steve, the latter of whom runs Stingo (Steve’s Bingo) on Wednesday evenings. You can win fabulous prizes (like free bags of chips and free shots), but the real draw is Steve’s hilarious deadpan delivery on the microphone.
When you get hungry, get someone to watch your Stingo card and head across the street to Taqueria San Jose. Order a chicken torta. It comes with the works. You won’t be sorry when you head back. You’ll get a light ribbing from Steve for bringing food into the bar, but it’s a small price to pay.
Oh and good luck getting home at 3 AM. You might have to spend the night.