Welcome, my globe-trotting, thrill-seeking listeners to “Things to Do in Chicago” on this fine Sunday, October 5, 2025. This is Oly Bennet—your favorite source for discovering the wild, wacky, and wonderful across the Windy City. This morning, Chicago’s got that early fall magic in the air: brisk, lively, and absolutely perfect for a day of adventure. The city’s streets are buzzing with bundled-up crowds, and even the squirrels are wearing their autumn best.

Today, the city is all about *variety*, and oh boy, does Chicago deliver! If you’re craving rare finds and vintage treasures, Modern Vintage Chicago turns Ravenswood Event Center into a one-day paradise for collectors and fashionistas—bring an eagle eye and channel your inner treasure hunter. Over in Hyde Park, families and fitness fans can lace up for the RBC Race for the Kids at Comer Children’s Hospital, adding a dash of heart and hustle to the morning. For your culture fix, the legendary Chicago Architecture Biennial keeps the city marveling with installations and urban spectacles, while the Destinos Latino Theater Fest energizes the National Museum of Mexican Art with vibrant performances that can make even the most stoic Midwesterners bust a move. If you’re the type who needs a snack and a stroll, don’t skip the Glenwood Sunday Market or the iconic Maxwell Street Market, where produce, pastries, and pop-up surprises fuel your day.

But wait, what’s that sound echoing from the Chicago Theatre? That’s none other than “John Candy I Like Me: An Evening with Ryan Reynolds & Friends!” Get ready for side-splitting comedy and celebrity antics, right under the marquee at 175 N State Street. If you’re more into quirky local traditions, look out for Jack’s Pumpkin Pop-Up on Goose Island, where corn mazes meet Chicago-sized seasonal energy—this is not your grandma’s pumpkin patch! Night owls, the ART on THE MART digital projections along the Riverwalk will light up your evening with mesmerizing creativity and some serious photo ops.

Chicago’s local news? The grand opening of Auntie Anne's + Cinnabon Co-Brand Flagship downtown means cinnamon-scented air and pretzel lovers unite. Transit riders, good news: extra express shuttles are navigating to and from the Burnham Wildlife Corridor for tonight’s Mid-Autumn Festival finale—mooncakes, music, and a lantern procession set the lakefront aglow. If you’re driving, keep an eye out for the city’s expanded street cleaning schedule and grab that spot early, unless you’re into post-event parking scavenger hunts (hey, some people call it sport!).

As far as must-dos, don’t miss ART on THE MART for an evening stroll—it’s like watching Picasso get wild with a laser pointer. The Lincoln Park Blues and Gangster Tour gives you a walking, talking history lesson straight from Chicago’s nefarious past. And for a local secret: If you’re aiming for truly legendary deep dish, take a detour to Pequod’s in Lincoln Park. Their caramelized crust is basically Chicago pizza in full beast mode—trust Oly, this is the taste bud trophy you want.

Want to fit in like a native? The first Sunday of every month means discounted museum entry for Illinois residents, so bring your state ID and map out a mini-culture marathon. Remember, in Chicago, jaywalking is an art form and umbrella defense is crucial—watch those wind gusts, folks!

Tomorrow, keep your eyes peeled for even more festivals, the start of Open House Chicago, and fall’s biggest food events. Whether you’re up for architecture tours, river rambles, or late-night laughs, this city’s got you covered.

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