13 Results
The Chicago Air and Water Show presented by Shell Oil Products U.S. and the City of Chicago is the largest FREE show of its kind in the United States. The show can be viewed along the lakefront from Fullerton to Oak Street on North Avenue Beach.
Chicago Boat, RV & Strictly Sail Show — Midwest boat and RV exhibition.
1-312-946-6242
send emailThe Chicago Yacht Club Race to MackinacⓇ is one of the largest annual offshore sailboat races in the world.
Bike the Drive brings cyclists onto Chicago’s DuSable Lake Shore Drive for a scenic ride with sweeping lake and skyline views. Riders can choose their distance and enjoy a post-ride festival in Grant Park, with rentals available.
1-844-299-2087
The unofficial start of the fair starts with the twilight parade and discounted carnival rides. The Twilight Parade starts at 6:00 pm from 9th Street and North Grand Avenue to the Grandstand. You won't want to miss the spectacle and pageantry.
1-217-782-6661
June 18-20, 2027 hot air balloon festival at Eagle Ridge Resort and Spa in Galena, Illinois. Launches, night glow, live music, and a cruise-in benefit Breakthrough T1D and Camp Hertko Hollow.
The Galesburg Great Balloon Race is a free family hot air balloon event at Lake Storey in Galesburg, Illinois. July 23-25, 2027 brings daytime launches, a special-shape balloon, and an evening glow. No rides for hire.
Balloons Over Mount Vernon is a continuing hot air balloon festival; the next edition is October 8–11, 2026.
1-618-242-7016
Christkindlmarket returns to Daley Plaza, Aurora, and Wrigleyville beginning November 20, 2026 (Daley Plaza through December 24).
1-312-494-2175
send emailThe Aquatic Experience is a continuing annual trade show; the 2026 edition is November 19–21, 2026 at McCormick Place.