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Monthly Guide

Monthly Guide

☀️ Your (bigger and better) guide to June!

June 2, 2026 · — Emmi Mack

Hey friends! As you might have noticed, your monthly guide is now bigger and better than ever. It’s got its own entire newsletter! You can expect this new package delivered straight to your inbox at the top of the month.

So, without further ado, let’s get into it!

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Team Tips and Picks

A man hugging another man from behind on stage with smoke in the background
“Brokeback Mountain” at Chicago Shakespeare Theater stars Harrison Ball as Ennis and Jack Cameron Kay. (Courtesy of Kyle Flubacker / Chicago Shakespeare Theater)

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.”

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Tickets to Get Now (Before It’s Too Late)

And, as always, stay tuned to your daily City Cast Chicago newsletter for even more summer fun.

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