Welcome, energetic explorers, to Things to Do in Chicago! It’s Saturday, October 25, 2025, and I’m Oly Bennet, your globe-trotting sports nut turned event adventurer, live from the city where the lakefront breeze could host its own kite festival and deep dish pizza is basically an Olympic event.

Chicago this morning is serving up what locals call “sweater weather”—a cool, crisp fall day that’ll have you clutching your coffee and snapping way too many pics of those golden leaves. Everyone’s buzzing, thanks to Halloween on the horizon and an avalanche of happenings crashing into your weekend.

First up, for you comedy junkies and improv lovers, Ben Schwartz and Friends are taking over The Chicago Theatre tonight at 8 p.m. Expect wild scenes, famous faces, and enough laughs to pull a muscle you didn’t know you had, straight outta the multiverse—seriously, this will fill up fast, so get there early, and maybe practice your improv prompt in line just in case you join the action.

If live music vibes are more your jam, head to the legendary Old Town School of Folk Music. There’s a double-header at 8 p.m. featuring the rootsy sounds of Tobacco City—a toe-tappin’ journey through Americana sure to leave your inner cowboy high-fiving your inner jazz cat. And if you’re feeling artsy, just a few blocks over Epiphany Center for the Arts is open for exploration with golden hour drinks, a pre-show buzz, and that gallery-rambling atmosphere that makes you feel instantly cooler.

Movie buffs, the Rooftop Cinema Club is screening Hocus Pocus tonight. Think classic witches, city skyline, popcorn, and all the cozy fall feels under the stars—bonus points if you show up in costume, because honestly, who isn’t ready to let their inner Sanderson sister run wild before Halloween?

Families and creative souls, check out BUILD Chicago with free drop-in art studios and science experiments through the afternoon at 5100 W Harrison Street—no fancy tickets or experience required, just curiosity and maybe a paint shirt you don’t mind covering in accidental masterpieces.

Photography fiends don’t miss the “Street” exhibition by Ann Kogen, open all day at Dittmar Gallery at Northwestern’s Norris Center. Take a time machine back to the 1980s through her stunning black-and-white street photos—think big hair, bold moments, and those raw slices of city life that never go out of style.

Splashing into news: According to local transit updates, the CTA is running extra trains tonight for safe shenanigans, and there’s buzz about a new ramen spot opening in Wicker Park—because nothing says autumn like hot noodles and bragging rights for trying the city’s swankiest slurp.

For today’s must-do list, make the most of Millennium Park's evolving fall color show, pop into the Chicago Cultural Center (always free and always fascinating), and sneak in a walk along the Riverwalk before the winter chill muscles in. If you’re craving a quirky adventure, jump on the L and pick a random stop—some of Chicago’s best treasures are hiding in the neighborhoods.

Oly’s local tip? If you want to feel like a true Chicagoan, layer up, leave the umbrella at home, and don’t be shy about asking your server for their favorite dish—they take local pride seriously, and you might discover something that makes your taste buds do the wave.

Tomorrow is packed with even more festivities—keep an eye out for gallery walks, pop-up brunches, and last-minute Halloween costume contests. I dare you to tune in again and see what wild, wonderful antics this city has in store.

Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.

For more check out https://www.quietperiodplease.com/

and make sure to jump on these great deals https://amzn.to/3V0gjPt

For more on Oly check out https://www.instagram.com/olybennet/

This content was created in partnership and with the help of Artificial Intelligence AI