After coming off a long holiday weekend, we know the perfect thing to get perk you up: planning a pub crawl with Chicago Trolley. This week, let’s explore Pilsen, the awesome and sometimes-forgotten jewel of Chicago’s nightlife neighborhoods. Go ahead and reserve your trolley now for your big night out, and in the meantime, feel free to check out our guide to pub crawling in Logan Square as well. Grab a few road beers and maybe some chips (but no dip — the ride can get bumpy) and let’s hit the road together!
Stop One: SkylarkIf we’re going to Pilsen, we may as well start with a bonafide neighborhood staple: Skylark, at 2149 S. Halsted St. This bar is the absolute perfect dive, complete with a great photo booth and starving artists lining the corners. Be sure to stop in again on Mondays for free jazz, which pairs nicely with a $2 PBR. As we’re going to see with a lot of the best Pilsen bars, the bar food at Skylark is top-notch, with an incredible burger and the best (the best) tater tots in the city.
Stop Two: Honky Tonk BBQNext up, let’s stop for a taste of red-blooded americana at Honky Tonk BBQ. Located at 1800 S. Racine Ave., you can’t beat the atmosphere or the daily live music at Honky Tonk. The cocktails are delicious, the beer list is solid, and if the words “bacon candy” don’t entice you, we don’t know what will. If you haven’t eaten dinner that night, this is the place to do it — the BBQ rib tips are on point.
Stop Three: The BarrelAfter getting a little fancy, let’s take this pub crawl back to the basics at The Barrel at 2015 S. Damen. The great thing about The Barrel is that it’s focused on local brews; from Revolution to Penrose, The Barrel features a Chicago-only beer list. The focus here is on the beer, but the cocktails are also great. Affordable and unique, The Barrel is a sure thing.
Stop Four: Simone’sIt’s right around this time you’ll want to head over to Simone’s and vibe out the DJs, nestled in the heart of Pilsen at 960 W. 18th St. The entire place is made out of recycled, repurposed materials, including the seats taken from airplanes and cars, a bar that’s a former bowling alley lane and a DJ booth made of retired pinball machines. The drink menu is huge, the bar food is tasty and, as an added bonus, it’s all very environmentally friendly. Simone’s is truly one-of-a-kind and a perfect example of how eclectic and fun Pilsen can be.
Stop Five: Punch HouseLastly, let’s move just down the street to the one and only Punch House. Located at 1227 W. 18th St., this basement bar is the perfect way to end the night — it’s open ’til 3 a.m. on Saturdays, and you and your pub crawl group can split just one or two of Punch House’s to-die-for punch bowl creations. The atmosphere is relaxed at one moment and a huge party the next, and the drinks are fantastic. (Bonus: If you can time it right, get there at midnight, when they feed the fish in the giant aquarium behind the bar. The staff sings a song to the fish and everyone in the bar does a shot. You can’t miss it.)
There are all sorts of places to drink, eat and see in Pilsen — these are just five of our favorites. Book a trolley and let’s do Pilsen right this weekend!