Distance from downtown: 3.7 miles Via: Red Line Best for: Comedy, history Go: Evening

Church picture

ST. MICHAEL’S CHURCH Although it is known as one of the few buildings that “survived” the Great Chicago Fire of 1871, all but the walls was destroyed. The rebuild was completed in about two years – one of the first churches to rise from the ashes. Founded as a haven for German immigrants, St. Michael’s remains a beacon of the neighborhood. As they say, if you can hear the bells of St. Michael’s, you know you’re in Old Town.


TWIN ANCHORS This unassuming rib joint is one of Chicago’s oldest and most iconic restaurants. It is located in an historic building that is thought to have housed a tavern as far back as 1910. During World War One, the Schlitz Brewing Company donated the bar that patrons still sidle up to today. The history and celebrity endorsements, however, pale in comparison to one bite of Twin Anchors’ fall-off-the-bone specialty – opt for the zesty sauce.


BENCHMARK Established in 2010, Benchmark’s atmosphere is squeaky-clean compared to Old Town’s more historic haunts. Its offerings include cold drinks, elevated bar fare, and enough TVs to ensure your game is on. But what makes it unique is on the second floor, the majority of which is covered by a retractable roof – Chicago’s first convertible beer garden.

Second City

SECOND CITY The improvisational comedy theater where superstar alumni such as John Belushi and Tina Fey honed their craft is located in Piper’s Alley, a 1960s hippie hot spot that has since become more commercial. Second City’s façade features four terra cotta portrait heads of German artists salvaged from Louis Sullivan’s Garrick Theater.


ZANIES For more comedy, head down the street to the original Zanies, which opened in a former strip club in 1978. The small venue features some rather big names in stand-up comedy. Audience members who don’t want to become the butt of a joke might want to snag a seat in the back.