The Best Comedy Events in Chicago Right Now: What’s Actually Worth Going To

Comedy events in Chicago are having a very real moment right now — and no, that’s not just something your friend who “almost took Second City classes once” is saying. With over 3,500 people already circling or committed to shows this week alone, it actually feels like the whole city is headed to a club, a back room, or a drag brunch. Whether you’re a North Side regular or you only come up here when there’s parking, this is a good time to lock in tickets instead of doom-scrolling through TikTok until midnight.

The lineups making the rounds in group chats are a mix of big-night-out and very Chicago weird. You’ve got Irish storytelling machine David Nihill hitting The Den Theatre (perfect for a proper sit-down, “we planned this” kind of night), and Samay Raina’s "Still Alive" tour already drawing in the die-hard fans calling dibs on that 2026 date like it’s a Taylor Swift presale. On the more local-heartstrings end, there’s F*ck Ovarian Cancer: Benefit for Ashley Silverman — one of those nights where comics show up with their A-game and the crowd actually listens between laughs. Events like 20x2 Chicago: What Can You Do? lean more alt-nerd variety show, while Bad Bunny Drag Brunch – Chicago is brunch-plus-chaos in the best way, and UpDating is for people who like their crowd work with a side of romantic disaster.

As for where to park yourself, the usual suspects are still doing the heavy lifting. Laugh Factory Chicago in Lakeview is your go-to if you want buzzy lineups and a big room that feels like a proper night out. Zanies in Old Town is for people who care about the craft and kind of like that it’s cramped and legendary (yes, you’re basically on the stage; no, that’s not a complaint). The Lincoln Lodge keeps pulling in the comics that other comics go to watch, so if you’re into offbeat shows and smart weirdos, that’s home base. Meanwhile, smaller rooms like The Den are where you catch touring acts in a space that still feels intimate enough for eye contact — whether you want it or not.

So if you’ve been telling yourself you’ll “check out a show sometime,” this is your sign to stop being theoretical about it. Pick your lane: a benefit show with actual feelings, a drag brunch that will wreck your Sunday productivity, a live dating experiment you’ll pretend you were dragged to, or a classic club night with a name you’ve already seen on YouTube. This is what discovery looks like in Chicago right now: you buy the ticket, you show up, and you leave with a new favorite comic you can brag about seeing before everyone else.