Looking for the best things to do in Chicago this weekend? Whether you’re planning a family outing or a night out with friends, the city has something exciting happening for everyone. From the sky-high thrills of the Chicago Air and Water Show to immersive arts festivals and pop culture extravaganzas, here are some top picks to add to your weekend itinerary.
✈️ Chicago Air and Water Show
📍 North Avenue Beach and Chicago Lakefront (Fullerton to Oak Street)
📅 Saturday & Sunday, August 16–17, 2025
⏰ 10:30 AM – 3:00 PM
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This iconic, free annual event is one of the largest air and water shows in the U.S., featuring thrilling aerobatic performances by the U.S. Air Force Thunderbirds, the U.S. Army Golden Knights parachute team, and spectacular watercraft demonstrations. Families can enjoy the lakefront views and festive atmosphere with food vendors and music along the beach. No tickets required; arrive early for best viewing spots.
🎨 Glenwood Avenue Arts Fest
📍 6900–7200 N. Glenwood Ave, Rogers Park, Chicago
📅 Friday, August 15 – Sunday, August 17, 2025
⏰ Friday: 6:00 PM – 10:00 PM
⏰ Saturday: 11:00 AM – 9:00 PM
⏰ Sunday: 11:00 AM – 7:00 PM
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The Glenwood Avenue Arts Fest (GAAF) is a free, weekend-long celebration of art and community in Chicago’s Rogers Park neighborhood. The festival features over 130 artists showcasing a diverse range of artworks, including ceramics, digital art, woodworking, and mixed media. Attendees can enjoy live music and dance performances on multiple stages, participate in interactive arts activities, and explore open studios. A dedicated KidFest area offers hands-on arts activities for children. The event takes place on the cobblestone streets of the Glenwood Avenue Arts District, just steps from the Morse CTA Red Line stop.
🦞 Great American Lobster Fest
📍 Navy Pier, 600 E. Grand Ave, Chicago
📅 Saturday, August 16 – Sunday, August 17, 2025
⏰ Saturday: 12:00 PM – 11:00 PM
⏰ Sunday: 12:00 PM – 8:00 PM
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Dive into a coastal culinary experience at Navy Pier’s Great American Lobster Fest, coinciding with the Chicago Air & Water Show. Savor a 1.25-pound Maine lobster served with corn on the cob, potatoes, a dinner roll, fresh-cut lemons, and melted butter. Each meal includes a drink ticket redeemable for options like Goose Island Beer, Coppola Diamond Prosecco, or a non-alcoholic beverage. Reserved seating areas offer views of Lake Michigan and the Chicago skyline, complemented by live music and games. Advance ticket purchase is recommended, with pricing varying by session.
🎮 Fan Expo Chicago 2025
📍 Donald E. Stephens Convention Center, 5555 N. River Rd, Rosemont, IL
📅 Friday, August 15 – Sunday, August 17, 2025
⏰ Friday: 4:00 PM – 9:00 PM
⏰ Saturday: 10:00 AM – 7:00 PM
⏰ Sunday: 10:00 AM – 5:00 PM
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Fan Expo Chicago is a premier pop culture convention featuring a diverse lineup of celebrities, artists, and creators.Highlights include appearances by Ewan McGregor, Hayden Christensen, Orlando Bloom, and Brendan Fraser. Attendees can enjoy panels, cosplay contests, gaming tournaments, and exclusive merchandise. The event is family-friendly, with special activities for all ages. Tickets range from $50 for single-day passes to $140 for family passes, with discounts available for youth and children. Advance purchase is recommended.
No matter your interests or age, Chicago is bursting with exciting events this weekend. From thrilling air shows and delicious lobster feasts to vibrant arts festivals and pop culture conventions, there’s something for everyone to enjoy. Be sure to plan ahead, grab your tickets if needed, and make the most of your weekend in the Windy City!
Missed out on last weekend’s excitement? Catch up here on all the unforgettable moments and highlights you won’t want to miss!