Welcome, adventurous listeners, to “Things to do in Chicago”—powered by Oly Bennet, your global passport to the planet’s most offbeat happenings, and today I’m tossing the Chicago playbook your way with a hearty high five. It’s Sunday, October 19, 2025, and if you haven’t noticed, Chicago is buzzing like a field goal in overtime! Cloudy skies are keeping temps cool, giving everyone an excuse to break out those fresh fall layers and fuel that café-hopping spirit.

First up in today’s Chicago saga: the Windy City is serving a literal marathon of events. For you early risers, the Chicago Lighthouse’s Rise to Shine 10K/5K/1M Run & Walk took over the streets at 8 AM—run for charity, stretch your legs, or, let’s be honest, stand on the sidelines with a coffee and cheer like it’s the sports championship of the year. Prefer cheering on art over athletes? The citywide Open House Chicago festival wraps up today, so it’s your last chance to sneak into dozens of architectural hidden gems that are usually locked up tighter than a hockey goalie’s gloves. Explore legendary spaces from the South Loop up to Uptown—snap a selfie, drop a jaw, repeat.

Culture vultures, your wings are needed at the West Loop Contemporary Fine Art Expo’s grand finale, bursting with new works from the city’s hottest up-and-coming artists. If tunes get your heart racing faster than a last-second buzzer beater, tonight at the Epiphany Center for the Arts offers a soulful set by Ken Fobs at 6 PM followed by a Candlelight Tribute to A.R. Rahman at 8:30. Now THAT’S a double-header.

Families and fun-lovers, Midtown Athletic Club is hosting their annual Fall Fest: think bouncy houses, pumpkin decorating, and enough seasonal snacks to keep you powered up for the world’s quirkiest sack race championships. If your tiny humans still have energy, Abbeye Farms’ Pumpkin Daze Fall Festival keeps the autumn charm alive with hayrides and a mega corn maze just beyond the city.

On the ticket of big city excitement, The Book of Mormon brings Broadway-level laughs to CIBC Theatre—catch their last show tonight. Feeling a bit spookier, Rocky Horror Picture Show’s 50th Anniversary Spectacular rolls into The Chicago Theatre. It’s interactive, it’s electric, it’s… definitely one for the story vault.

Let’s shoot over to local buzz—Chicago just welcomed new restaurants in River North serving Detroit-style pizza that’s so thick, you could use it for shot put practice. The L reroutes around the Loop are done for the weekend, so transit riders have full reign—slide onto the Red Line and chase the action from Sox Park to Lincoln Park.

Craving the ‘only-in-Chicago’ experience? Wander out to the DANK Haus German American Cultural Center’s open house for a stein or some bratwurst, or stroll by the lakeshore and catch wind surfers who look like they’re auditioning for the city’s next zany sporting league. Looking for the underdog? Hunt down one of those classic neighborhood jazz brunches, where the mimosas flow as smooth as the trumpet solos.

Chicago always holds a trick up its sleeve: Did you know the city’s alleys total nearly 1,900 miles—more than the distance from Chicago to Miami? Only here could you find postmodern masterpieces (and a secret bocce court) by just wandering off the main drag. So trust your feet, trust your gut, and don’t be surprised if you stumble into your new favorite haunt.

Keep your calendars handy, because tomorrow, the Chicago Architecture Center rolls out encore tours, and don’t miss the golden-hour live music at Epiphany Center’s Café Bar—hello, half-price wine and acoustic vibes!

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