Second City Theater, Chicago (must see)

The crown jewel of Old Town's entertainment scene, this comedy club is known for first-class acts who ascended to stardom on the silver screen. The names of comedy titans like Mike Myers, Bill Murray, John Belushi, and Tina Fey grace its "Foyer of Fame."

A hub of cultural relevance and uproarious humor, the place consistently draws crowds, creating an electric atmosphere, though visitors should come prepared for a healthy dose of colorful language and progressive political commentary. Portions of the performances involve interactive improvisation with the audience; in fact, the grand finale, occurring around 10:30pm, is just that, and no ticket is required to attend as the cast tries out new comedic material. Seats are otherwise considered first-come, first-served, so be sure to arrive 20-30 minutes early if you want the full experience or opt to secure reserved seats along the rail for an added fee.

It's worth noting that beyond the Second City Theater, this complex houses a Sony Multiplex cinema, as well as a variety of restaurants and even a Starbucks. The theater's mainstage entrance features elegant stone arches adorned with faces originally from the Adler and Sullivan-designed Garrick Theater.

Tip:
For a glimpse into Old Town's beatnik history, venture to the time-honored OLD TOWN ALE HOUSE (Sun-Fri: 3pm–4am; Sat: 3pm–5am), famed for its proximity to Second City and the cast's penchant for hanging out there after performances. With its vintage decor and a lending library, the place oozes character from every nook and cranny. It's a lively spot, particularly on weekends, where the vivacity adds to the fun. Don't forget to check the mural behind the bar, paying a tribute to Second City legends like John Belushi and Bill Murray.