Welcome to “Things To Do in Chicago” for Saturday, August 16, 2025! Whether you’re a local looking to spice up your day or a visitor ready to dive into the Windy City’s pulse, we’ve got today’s must-see events, cultural highlights, and local news—plus tips to make the most of Chicago’s summer scene.

First, let’s set the vibe: It’s a classic August day with balmy summer weather, making it prime time to be outside. The air quality is moderate and ideal for strolling along the lakefront, and there’s a buzz in the city thanks to one of Chicago’s biggest annual spectacles hitting the skies.

Your top events for today:

- The Chicago Air and Water Show is roaring overhead from 10:30 a.m. to 3:00 p.m., free and visible along the entire lakefront from Fullerton to Oak Street with the main action centered at North Avenue Beach. Watch jets and parachuters perform daring feats above Lake Michigan, a highlight that draws crowds from across the Midwest[4].
- Dive into the tastes, sounds, and culture of Italy at the Taylor Street Little Italy Festival, running noon to 10 p.m. Sample classic cannoli, dance to live music, and experience old-school neighborhood charm in the heart of Little Italy[1].
- If you’re a treasure hunter or vintage lover, don’t miss the Chicago Vintage Festival in Bucktown. Discover unique clothing, cool collectibles, and retro vibes from 12 p.m. to 6 p.m. at the Village Bucktown Dispensary—family-friendly and open to all ages[7].
- For theater fans, Tony-winning musical “Parade” is at the CIBC Theatre, and the crowd-favorite “MJ” about Michael Jackson runs at the James M. Nederlander Theatre, making downtown a hotspot for performing arts tonight[6].
- More into music? Enjoy “Candlelight: A Tribute to Coldplay” at the Arts Center of Oak Park for a magical, string quartet take on modern classics—or catch concerts headlined by Andy Grammer, Jessie Murph, The Offspring, and others across Chicago’s lively music scene[10].

In local news, Chicagoans are talking about several hot topics: The Air and Water Show is leading headlines after some high-flying rehearsals rattled windows yesterday. Meanwhile, public schools are under the spotlight after the board pressed pause on the latest CPS budget proposals, signaling debates ahead for the fall[2][8]. Also, Mayor Johnson’s approval ratings are in the news, and be aware that there’s a temporary spike in Southwest Side burglaries, so take precautions if you’re in those neighborhoods[2].

Today’s a perfect day for classic Chicago activities: Try the Big Bus Hop-On, Hop-Off Tour and visit icons like Millennium Park, the Art Institute, the Riverwalk, and Navy Pier—all easy to reach and buzzing with summer energy[3]. For a low-key hidden gem, consider an evening bonfire at a South Side park, accessible via public transit, and a favorite among locals for sunset views and great music[9]. If you’re seeking a family adventure, the Lincoln Park Zoo and Chicago Cultural Center have free events and exhibitions on offer[6].

Local tip: The best spot for the Air and Water Show isn’t always the most crowded—head a bit north or south along the lakefront for a laid-back atmosphere and just-as-stunning views. Bring sunscreen and cash for food trucks!

Finally, don’t miss tomorrow’s events: The Air and Water Show returns for its grand finale, and several summer street festivals kick off across different neighborhoods. Be sure to tune in again for your daily guide to Chicago’s best!

Whatever you do, soak in the summer energy—Chicago is alive with possibility today!

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