Chicago’s Most Unexpected Comedy Venues

Find laughs in offbeat places

Photo courtesy of The Hideout

With seemingly endless options, the Chicago stand-up landscape can be daunting to navigate. Shows come and go, open mics appear (or disappear) overnight and traditional comedy clubs don’t offer the gritty intimacy one might find in the back room of a tavern. Certainly “gritty intimacy” isn’t for everyone, and those looking to avoid graffitied bathrooms or $2 PBRs are best advised to stick to the glint and polish of said clubs.

But for folks looking to experience a different side of Chicago’s stand-up realm, options abound. Countless bars across the city offer weekly or monthly comedy nights, but there are a handful of places that embrace comedy to the extent of offering several different shows and supporting both comedians and audiences alike. These are their stories (cue Law & Order *dun dun*)

Cole’s; Credit: Toby McMullen

The Hideout
This historic bar/venue/prohibition-era speakeasy has been a favorite of misfits and music-lovers for a century, so it’s no surprise that the establishment (and its familial, cult-like following) welcomes a wide variety of stand-up shows. In addition to weekly and monthly shows, The Hideout is a popular choice for touring comedians who eschew comedy clubs and might not fill larger venues—or even when a bigger name can fill a theater, sometimes they prefer the cozy setting offered by this wooden stalwart for the arts (in 2012 Aziz Ansari announced a two-night run of last-minute shows at the Hideout, which promptly sold out). Currently, the venue has comedy scheduled every Monday evening, featuring a different show each week. Stand-up, variety and a monthly show curated by The Onion’s ClickHole writers finds a little something for everyone.

@North Bar
This Wicker Park mainstay is to stand-up comedy as beercades are to video game aficionados. The owners, who are huge comedy fans, offer a platform to myriad local comedians for one-off shows, one-person shows and weekly showcases. The bar is another popular spot for touring comedians looking to do one-nighters in Chicago, as the space is small yet comfortable, and it’s much easier to fill than most spots. Keep a lookout for bigger names from New York and Los Angeles stopping in for shows, Geoff Tate and Shane Mauss.

Cafe Mustache
The aptly named coffee shop/bar/music venue is frequented by a full spectrum of hipster clientele, but the stereotype is shed when it comes to the space’s performance offerings. While live music dominates the monthly calendar, Cafe Mustache is home to a number of alt-comedy shows ranging from stand-up to storytelling to outright silly fun.

Gallery Cabaret
Another music-focused venue with a penchant for local comedy, this Bucktown gem has long been a proponent of the Chicago stand-up scene. Like The Hideout and Cafe Mustache, this can be attributed to the bar’s quirky nature and devoted regulars. It hosts four weekly stand-up shows (Two Hour Comedy Hour, Comedy Overload, Cupcake Cabaret and Power Hour), each with its own twist, theme and gimmicks. Every comedy show is inevitably followed by live music of all different genres, so if you’re looking to kill two entertaining birds with one stone, Gallery Cabaret is a solid bet.

Cole’s Bar
At the risk of sounding redundant, Cole’s Bar is yet another venue joining these ranks of musical venues with a soft spot for funny business. The first comedy show to call Cole’s home (shortly after the bar opened for business) is still running. In fact, Cole’s Open Mic is one of the longest running comedy mics in the city, with a solid lineage of comedians at the helm. Most of the other shows at the bar are monthly or one-off shows, but Cole himself is a great supporter of the local comedy scene.

Under the Gun Theater
The only venue on this list that doesn’t showcase live music, Under the Gun Theater is home to a couple of the city’s best and most beloved shows: The Lincoln Lodge and The Blackout Diaries. The venue also hosts several other weekly, monthly and one-off shows, and features a full bar, which is a pleasant surprise if you’ve ever frequented black box theater shows. The space is also home to Stand Up Seminary and Feminine Comique, two stand-up comedy classes under the umbrella of The Lincoln Lodge and Tight Five Productions.