
Monthly Guide
☀️ Your (bigger and better) guide to June!
June 2, 2026 · — Emmi Mack

Team Tips and Picks

Every month, the City Cast Chicago team tells you what we’re eating, where we’re shopping, and what else we’re planning for.
Emmi: A Trip (or 2) to the Theater
“Brokeback Mountain” at Chicago Shakespeare Theater runs through June 28. I’m so curious to see how the story translates to the stage. (I hear there’s a live country band!) I’m also looking forward to “Catch as Can Can” at Steppenwolf starring my “Veep” favorite, Gary Cole.
Jacoby: Performing Live With a Side of Fries
I’ve got a few performances coming up this month, including Write Club at Gman Tavern June 9 and the first-ever Moth Slam at the Beverly Arts Center June 24. I really want to try the bone marrow parmesan fries at Open Outcry Brewing down the street from BAC.
Michelle: Free Music, Movies, and Workouts at the Park
Grant Park Music Festival kicks off on June 10 with “West Side Story,” led by artistic director and principal conductor Giancarlo Guerrero. (You might have seen Guerrero in Bad Bunny’s Super Bowl halftime show.) Millennium Park Summer Music Series also starts June 15, with concerts every Monday and Thursday until August. Millennium Park has free summer workouts too!
Simone: Out With the Old, in With the Style
After the seasonal closet turnover, I find myself with three bags of clothes that don’t fit and nothing to wear to my friend’s wedding this month. I’d like to organize a clothing swap and donate leftovers. But I may still end up back at the thrift store.
Chima: Hip Hop and Feeling Retro
Last year I missed out on the first shapesFEST at Navy Pier, but they’re running it back June 19, and I’ve already got my outfit in mind. This month, I’ll also be deep in my nostalgia bag, playing old games at Logan Arcade and watching “Toy Story” one through four before I see “Toy Story 5.”

Tickets to Get Now (Before It’s Too Late)
- 🎤 June 6: femdot. Presents You Just Had To Be There | Ramova Theatre | Bridgeport
- 🎵 June 7: Melissa Etheridge | Brookfield Zoo
- 🚢 June 12-14: Windy City Boat and Yacht Show | Burnham Harbor | Near South Side
- 🏳️🌈 June 13: Pride Night | Shedd Aquarium | Museum Campus
- 🎞️ June 13: “Grosse Point Blank” with John Cusack | The Auditorium | Loop
- ⚾️ June 13: Sox Crawl Fiesta | Sox Park | Bridgeport
- 🎥 June 14: “Stand by Me” with stars | Chicago Theatre | Loop
- ⛴️ June 18-21: Black Yacht Weekend | Various locations
- 🎶 June 19: Son Rompe Pera | Thalia Hall | Pilsen
- 🏳️🌈 June 20: Embodied: A Pride x Juneteenth Variety Show | Thalia Hall | Pilsen
- 🏍️ June 19-21: Motoblot | Halsted Street between 35th and 37th | Bridgeport
- 🎵 June 26: Lionel Richie and Earth, Wind & Fire | United Center | Near West Side
- 🤠 Through June 28: “Brokeback Mountain” | Chicago Shakespeare Theater | Navy Pier
And, as always, stay tuned to your daily City Cast Chicago newsletter for even more summer fun.
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