Pub Crawl with Chicago Trolley: Boystown

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March 28, 2017

In the heart of Lakeview, the Boystown neighborhood preserves itself as a classic Chicago party scene. Catering specifically to the LGBTQ community, Boystown boasts some of the city’s most colorful and lively nightlife destinations. With Chicago Trolley transportation and a little bit of Boystown magic provided by the bars described below, you and your party can have the best Boystown Pub Crawl ever!

Stop One: Sidetrack

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[Image: @sidetrackbar via Instagram]

Start your pub crawl off right with the gigantic, fast-paced experience of Sidetrack. Located at 3349 North Halsted, this multilevel gay club features several bars and a rooftop deck! One of Sidetrack’s most popular theme nights is “Musical Mondays,” paying homage to the classics of Broadway through music, film and dancing. Whether it’s “Musical Mondays” or “All Things Beyoncé,” Sidetrack is the perfect place to kick off a wild night.

Stop Two: Progress Bar

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[Image: @progressbarchi via Instagram]

The second stop on your crawl is Sidetrack’s next-door neighbor: Progress Bar. Situated on the corner of Halsted and Roscoe, Progress Bar is a more laid-back bar experience. On entering, you’ll be drawn in by the massive cloud sculpture hanging overhead, made up of thousands of twinkling lights. Once your initial awe has worn off, you’ll notice on the bar’s extensive craft beer selection (we think it’s the best in the neighborhood). Be sure to drink a few local brews before heading back to the trolley.

Stop Three: Matilda

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[Image: @14eastmag via Instagram]

This next stop isn’t technically in Boystown, but any pub crawl in Lakeview would be remiss without it. Take the trolley from Halsted over to 3101 North Sheffield to visit Matilda, a 23+ bar with a classy atmosphere. Sip on a cocktail while lounging on posh furniture and listening to smooth jams. Matilda is a well-deserved rest after the first two stops, but don’t get too comfortable yet, because the night is just getting started!

Stop Four: Kit Kat Lounge

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[Image: @kitkatlounge via Instagram]

Time to jump back into the Boystown party scene. Located at 3700 North Halsted, Kit Kat Lounge features some of Chicago’s best drag shows and performers, impersonating a variety of Hollywood icons from the past century. Even better, the bar offers over 200 unique cocktails to choose from. So order yourself a fancy drink, sit back and enjoy the show. Or shake it out on the dance floor, if that’s your style.

Stop Five: Town Hall Pub

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[Image: @townhallpub via Instagram]

After a long night of partying, there’s no better place to end your Boystown pub crawl than the classic dive bar known as Town Hall Pub. This low-key stronghold at 3340 North Halsted is one of the oldest bars in the neighborhood, as evidenced by the stiff drinks, friendly staff, and comfortable atmosphere. The lights are dim, the booze is cheap, and good times are inevitable (especially on Wednesdays when comedians read hilarious Craigslist ads).


Boystown is a hub of vibrant Chicago nightlife. Whether you follow our route or design your own, booking a trolley for the night is only going to make your pub crawl easier and more fun. Reserve your trolley today, and let’s explore Boystown!