Football season is officially back! That means fans will be tackling lots of chicken wings throughout the season. ‘ In fact, chicken wing orders are the most popular game day food in NFL cities across the country — with a 25% increase in sales on game day (a.k.a. Sunday). And, for many fans, the … [Read more...] about Enjoy free bucket of chicken wings at KFC this football season
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Chicago Fall Market for Makers
Celebrate the work of independent artists and makers specializing in home decor, fashion, art, design, food and more at the Chicago Fall Market for Makers on October 24- 25, 2026, in the Ravenswood neighborhood. Score one-of-a-kind deals and support small businesses at this market, which … [Read more...] about Chicago Fall Market for Makers
Oktoberfestiversary
Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 10-11, 2026, in the Ravenswood neighborhood. Enjoy brews, live music and food in the spirit of the season. Sip on special tapings from Beglye and Dovetail while munching on … [Read more...] about Oktoberfestiversary
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 19 to November 1, 2026. 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
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the beloved Lincoln Square Ravenswood Apple Fest, October 2-4, 2026. Celebrate the new season with a bounty of edible goodness. Midwest farms will be serving up fresh apples and related dishes and local restaurants and … [Read more...] about Lincoln Square Ravenswood Apple Fest
Chicago Live! at Navy Pier
Witness the excitement of Chicago's extensive performing arts scene during the sixth annual Chicago Live! festival on September 19-20, 2026. Navy Pier will host free, non-stop performances featuring Chicago dance, theater, music and more during the two-day event. The breadth of Chicago's … [Read more...] about Chicago Live! at Navy Pier
First Lady Fall Cruises
One of Chicago's most iconic experiences is sailing on the scenic Chicago Architecture Center (CAC) River Cruise aboard First Lady and absorbing the city's stunning skyline while learning about its design history. The fun continues through the fall, with cruises floating along the shore … [Read more...] about First Lady Fall Cruises
St. Alphonsus Oktoberfest Chicago
It's that time of year when Chicagoans welcome the autumn season with polka, lederhosen and lots and lots of beer. St. Alphonsus Church celebrates its 24th annual Oktoberfest Chicago in the West Lakeview neighborhood with Bavarian food, live music and craft beer tasting on September 25-27, … [Read more...] about St. Alphonsus Oktoberfest Chicago
Free and cheap things to do this weekend in Chicago
Looking for something fun to do this weekend in Chicago? There are tons of free and cheap events in the city. Here’s our list of the top free events, discounts, and deals to have fun around town on your Friday, Saturday, and Sunday. There are many diverse events, so choose your favorite. … [Read more...] about Free and cheap things to do this weekend in Chicago
Enjoy free Chicken Shack Sandwich or Lettuce Wrap at Shake Shack every week
Shake Shack is definitely known for its juicy burgers and creamy shakes, but there is also a delicious option for chicken sandwich fans on the menu. And, for a limited time, customers can enjoy big savings on a Chicken Shack Sandwich or Chicken Shack Lettuce Wrap every week at the popular … [Read more...] about Enjoy free Chicken Shack Sandwich or Lettuce Wrap at Shake Shack every week
Destinos Chicago Latino Theater Festival
Celebrate Hispanic Heritage Month along with Latino theater and dramatic creativity at the ninth annual Destinos: Chicago International Latino Theater Festival for three weeks from September 14 to October 11, 2026, at theaters across the city. The Chicago Latino Theater Alliance … [Read more...] about Destinos Chicago Latino Theater Festival
Hyde Park Jazz Festival
Venues across the Hyde Park, Kenwood and Washington Park neighborhoods will come alive with live jazz during the 20th annual Hyde Park Jazz Festival on September 26-27, 2026. Music lovers will enjoy 34 free performances of local, national and international artists at a varied assortment of … [Read more...] about Hyde Park Jazz Festival
St. Benedict’s Oktoberfest
Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 60th annual St. Benedict Oktoberfest on October 2-4, 2026. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest
Riverwalk Fall Fest
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 19- October 31, 2026. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along … [Read more...] about Riverwalk Fall Fest
World Dumpling Fest
Explore Chicago's diverse cultures with music, dance and samples of all the variations of ethnic dumplings during the annual World Dumpling Fest on September 19-20, 2026, in the Lincoln Park neighborhood. The Chicago Cultural Alliance hosts the sixth annual World Dumpling Fest to support and … [Read more...] about World Dumpling Fest
