Pub Crawl With Chicago Trolley: Bridgeport

Header Image
January 31, 2017

Bridgeport is a South Side neighborhood with lots of old-school Chicago charm – meaning it’s perfect for knocking back a couple of brewskies in bars that are like diamonds in the rough. Gather your friends and reserve your trolley now for your big night out in this South Side haven.


Stop One: The Duck Inn

Kick off the crawl with class at The Duck Inn. Craft cocktails and appetizers will get you excited for your night ahead in this bar that’s located at the border of Bridgeport and the Lower West Side. Experience unique food and drink in a low-key neighborhood that will make you feel like you’re dining in ritzy River North!


Stop Two: Bernice’s Tavern

No fuss, no muss – just good brews and friendly people. That’s what Bernice is all about! This go-to bar for locals is also home to open mic nights, so your whole crew and enjoy live entertainment while imbibing cheap beer. No live music? Just take your pick at the classic jukebox. If you’re lucky, you’ll get to meet Bernice herself!


Step Three: Turtle’s Bar & Grill

Things are about to get Italian up in Bridgeport! There’s no mistaking Turtle’s with its Miller Lite mural on the side of the building. Turtle’s not only has amazing pasta dishes with vodka sauce – their vodka drinks aren’t bad either! Cozy up with a cocktail at the bar and order some snacks. You can’t leave before you’ve tried one of their famous flavored egg rolls. Their specials change daily, so you never know if you’ll wind up with a pizza egg roll or a buffalo chicken egg roll!


Stop Four: Maria’s Packaged Goods

Does it get any more Bridgeport than Maria’s? We didn’t think so. This neighborhood staple is filled with 300-plus microbrews, chandeliers made out of bottles, and a backroom with classic cocktails and live music. You simply can’t leave Bridgeport without spending quality time at Maria’s.


Stop Five: Mitchell’s Tap

Mitchell’s is the kind of charming neighborhood bar that you could easily lose several hours and several dollars to. Look for the Sox sign out front and get ready to end your night shouting, “Go Sox!” with die-hard Sox fans. The friendly bartender sticks to the area’s “third-round’s-on-us custom” so this is the perfect place to end the night if you’re still up for their amazing selection of beers.