Welcome to “Things to do in Chicago” for Sunday, July 27, 2025! Whether you’re a local or a visitor, we’re here to help you make the most of your day in the Windy City.
After a weekend of powerful thunderstorms and record rainfall that brought flash flooding to parts of the city on Friday, Chicago is shaking off the wet weather and buzzing with energy as festival season peaks. Be sure to keep an umbrella handy—while the skies are mostly clearing, some spots may still have standing water and scattered showers in the forecast[2][8]. The city feels vibrant, fresh, and just a little steamy, with a lively pulse fueled by art, food, and culture.
Top picks to make today unforgettable:
- Immerse yourself in global comedy at the final day of iO Fest, Chicago’s largest improv festival, featuring over 120 acts and headliners like 3Peat, 2Square, and Improvised Shakespeare. It’s all happening at the iO Theater in Lincoln Park—don’t miss your chance to see world-class improv in the city that invented it[4].
- Celebrate the 46th Annual Chinatown Summer Fair—a beloved street festival with a lion dance procession at 12:30 p.m., music and martial arts, arts and crafts, mouthwatering street food, and a bustling children’s area. Admission is free, and you’ll find it on Wentworth Avenue near Cermak. It’s a joyful, family-friendly event and one of Chicago’s most colorful neighborhood gatherings[7].
- For a cultural afternoon, step into “Blondell Cummings: Dance as Moving Pictures” at the Chicago Cultural Center. This free exhibition highlights the influential work of choreographer Blondell Cummings, connecting postmodern dance with the traditions of Black home life. It’s a unique way to experience movement, photography, and history all in one[10].
- Looking for fitness inspiration? River North is hosting the Faces of Fitness Chicago festival through early afternoon—a Lollapalooza for fitness fans with classes, demos, and wellness activities. Perfect if you want to kickstart your Sunday with some self-care[6].
- If you want spectacle and wonder, Teatro Zinzanni is back inside the Spiegeltent ZaZou downtown, dazzling guests with a mix of circus, cabaret, and creative cuisine[9].
In local news, Mayor Brandon Johnson announced he won’t propose a property tax hike for the new budget, instead pledging to pursue progressive revenue streams to cover the city’s $1.2 billion deficit—a move earning attention from both homeowners and renters[5]. On the food scene, keep your eyes open: several new restaurants are set to open later this month, especially near the Riverwalk and South Loop. Transit is running normally, but check for residual bus reroutes in areas hit hardest by Friday’s flooding[8].
No day in Chicago is complete without time on the Riverwalk or a stroll through Millennium Park. Snap a selfie by The Bean, explore the Franz West art installations, or grab a deep-dish slice at a local institution[3][6]. For something a bit off the beaten path, hop on a Big Bus Tour for a hop-on, hop-off adventure through Chicago’s landmark neighborhoods—an easy way to see the city like a pro[6].
Insider tip: When at the Chinatown festival, look for Mongolian beef buns at stalls near Cermak and 23rd—they’re a local favorite, and the lines move fast if you order before 2 p.m.
Before you go, mark your calendars for tomorrow! The Messi Experience Chicago continues—an immersive, interactive exhibition for soccer fans young and old[6]. Stay tuned for all the details on tomorrow’s hottest happenings. Thanks for joining us today, and happy exploring!