Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 20-October 25, 2025. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along the … [Read more...] about Riverwalk Fall Fest
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St. Benedict’s Oktoberfest
Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 59th annual St. Benedict Oktoberfest on October 3-5, 2025. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest
Randolph Street Market
In honor of the fall season, Chicago's signature open-air market, the Randolph Street Market, is hosting its fall market with vintage treasures, live bands, food and fun on September 27-28, 2025, in the West Loop. Celebrating 22 years, the Randolph Street Market Festival features an … [Read more...] about Randolph Street Market
Jack’s Pumpkin Pop Up
Wander through pumpkin patches and corn mazes while you enjoy the season at Chicago's largest fall festival, Jack's Pumpkin Pop Up, located near Goose Island, from September 18 to November 2, 2025. The large number of all-ages festivities make Jack's one of the most popular fall excursions. … [Read more...] about Jack’s Pumpkin Pop Up
Free Sundays on State
State Street, that great street, will be closed to traffic and open for an interactive, fun-filled block party in the heart of the Loop. Sundays on State is scheduled this summer for September 7 and October 5, 2025. From 11 to 6 pm on the designated Sundays, State Street between Lake and … [Read more...] about Free Sundays on State
Free Lincoln Park Zoo Fall Fest
Celebrate the joys of autumn in the fun-filled setting of Lincoln Park Zoo during the ninth annual Lincoln Park Zoo Fall Fest, September 26-October 26, 2025. Step into the vibrant world of pumpkins, harvest mazes and fall photo ops during this family-friendly event. Admission to the zoo is … [Read more...] about Free Lincoln Park Zoo Fall Fest
Art on the Mart
Stroll through the Riverwalk for views of one of the world's largest digital art platforms. ART on THE MART displays contemporary art projections across the 2.5-acre facade of THE MART. The fall show features artists from Arts of Life on Thursdays and Fridays from September 11- October 5, 2025 … [Read more...] about Art on the Mart
Free Chicago Air and Water Show
One of the most anticipated events of the Summer is the thrilling Chicago Air and Water Show. For over six decades, Chicagoans have witnessed the exciting spectacle of pilots and parachutists performing daring tricks over Lake Michigan. The largest show of its kind in the U.S., this … [Read more...] about Free Chicago Air and Water Show
Wrigleyville Night Market
Summer nights just got more exciting with the start of the weekly Wrigleyville Night Markets at Gallagher Way, kicking off on July 10, 2025, through September 18, 2025. Enjoy strolling through over 50 vendors displaying vintage clothing, jewelry, home goods and lots of unexpected finds. … [Read more...] about Wrigleyville Night Market
Chicago Full Moon Fire Jam
The full moon is celebrated in many ways in different cultures but in Chicago, fire dancers and percussion are the highlights of the annual summer Full Moon Jam. Glowing along the shores of Lake Michigan, this year's full moon jams will take place on July 10, August 8 and September 8, … [Read more...] about Chicago Full Moon Fire Jam
Buckingham Fountain Opening Day Events
Chicago's official start of the summer season always coincides with the spectacular splash of the first drops of the iconic Buckingham Fountain. This year's Switch on Summer Kick Off at Buckingham Fountain is set for May 10, 2025. Head to the fountain at 331 E. Randolph from 11:30 … [Read more...] about Buckingham Fountain Opening Day Events
Things To Do In Chicago in May
With spring weather warming up more consistently and the lakefront thawing into lovely aquamarine waves, May is a favorite time to explore Chicago before the large summer tourist crowds arrive. Consider these free or low-cost activities for your Chicago May adventures. Besides the essential … [Read more...] about Things To Do In Chicago in May
