Welcome to “Things to Do in Chicago,” your go-to guide for exploring the Windy City on Saturday, August 23, 2025! Whether you’re a longtime local or a first-time visitor, get ready for an exciting day packed with art, music, delicious food, and Chicago’s one-of-a-kind summer spirit.
Starting off, Chicago is buzzing this Saturday under warm late-summer skies—expect temperatures in the upper 70s, perfect for both indoor and outdoor adventures. Air quality is in the “good” range, so breathe easy while you make the most of the city. The overall mood is lively, with crowds gathering for major festivals and families enjoying the last weeks before back-to-school.
Here’s what’s happening today across Chicago:
- The 10th annual Thirsty Ears Festival turns Wilson Avenue into an open-air celebration of classical music. From 2:00 to 11:00 p.m., enjoy performances by stellar ensembles, food trucks, local beer, wine, and kid-friendly activities. For just $10, this is a must for music lovers and families alike[1][10].
- Pizza fanatics, gather at Pizza City Fest! From 5:00 to 10:00 p.m. at 430 N. Rush Street, sample slices from Chicago’s top pizzerias—think Angelo’s Stuffed Pizza, Nancy’s, Home Run Inn, and more. Live bands will set the mood so you can dance between bites[4].
- Whiskey aficionados, don’t miss the Chicago Summer Whiskey Tasting Festival at Galeria Chicago (2:30–6:00 p.m.), where you can test your palate on dozens of curated pours and chat with local distillers[7].
- If you want a classic city tour, the Big Bus Hop-On, Hop-Off Tour is running all day, making 11 stops at iconic sites like Millennium Park, The Art Institute, Navy Pier, and the Chicago Riverwalk. Great for explorers and families looking to cover a lot in one day[6].
- The Green City Market in Lincoln Park offers fresh, sustainable produce, delicious baked treats, and a relaxed community vibe every Saturday morning—a great stop for foodies or those planning a picnic[10].
On the city news front, Chicago is making headlines nationally: President Trump has threatened to send the National Guard to Chicago due to concerns about public safety, sparking robust responses from city leadership. Mayor Brandon Johnson has assured residents that the city remains focused on local solutions and public engagement. Encouragingly, official stats show that overall crime is down by 13% compared to last year, with especially sharp drops in robberies and murders, highlighting the progress Chicago is making[2][5][8].
Restaurant fans, take note—new openings and pop-ups abound! Several pizza spots from the festival lineup have announced permanent locations, and the Riverwalk is home to some of the city’s freshest bites and best people-watching opportunities[4][9].
Not sure what to do this afternoon? Here are a few “don’t-miss” ideas:
- Snap the ultimate selfie at Cloud Gate (“The Bean”) in Millennium Park, then wander through Lurie Garden[3].
- Visit The Art Institute of Chicago to see masterpieces by Van Gogh and Monet[3].
- Take in stunning city views from the 360 Chicago Observation Deck[3].
- If you crave urban adventure, grab a Divvy bike and cruise the Lakefront Trail or explore Chicago’s neighborhood street art[9].
Local tip: The CTA’s ‘L’ trains are your best friend—buy a one-day Ventra pass for unlimited rides and skip downtown traffic. For something extra cool, hop off at 18th Street and check out the vibrant murals and tacos in Pilsen.
And don’t forget—tomorrow brings the second day of the Thirsty Ears Festival, more market shopping, and hidden speakeasies with secret jazz sets. Check back in for tomorrow’s top picks and insider tips. Enjoy your Chicago Saturday—there’s always something new around the corner!