Here are some of the best things to do in Chicago this weekend (August 16-17, 2025):

• Chicago Air & Water Show: A spectacular free event running Saturday and Sunday from 10:30 a.m. to 3 p.m. along the lakefront with aerial performances by the U.S. Air Force Thunderbirds and more.
• Great American Lobster Fest: A seafood lover’s paradise at Navy Pier with all-you-can-eat lobster, music, and regional flavors.
• Taylor Street Little Italy Festa: Celebrating Italian culture with food, live performances, and family activities from August 14-17.
• Glenwood Avenue Arts Festival: An arts festival in Rogers Park featuring over 100 artist booths, galleries, and live entertainment (free event).
• Bronzeville Jazz-Music Festival: Outdoor jazz music festival on Saturday, August 16 from 10 a.m. to 10 p.m. (free).
• Neon Paddle: A night event with neon lights, paddleboarding, and live music at Ping Tom Memorial Park on Saturday.
• Various Air & Water Show viewing parties and cruises around Oak Street Beach.
• Rock the Rooftop: Classic rock music at AIRE Rooftop on Sunday evening.
• Other events include concerts, theater shows, markets, vintage festivals, food festivals, and sports games.

Whether you want outdoor festivals, live music, cultural events, or to watch the iconic Air & Water Show, Chicago is vibrant and full of exciting activities this weekend. Let me know if you want details on any specific event or type of activity! This overview combines free events and ticketed experiences for a great variety of options to enjoy Chicago this weekend.