THIS WEEKEND IN CHICAGO – Enjoying the Many Gifts of the Fall Season!
Believe it or not, it’s already the first official fall weekend of the season. And as usual, the city has pulled out all the stops so we can enjoy the many gifts that fall has to offer us. Let’s check it out!
Enjoy one of Chicago’s most mouth-watering events this Saturday and Sunday (11:30 a.m.-9 p.m.) at WingOut Chicago 2026 at Gallagher Way (3635 N. Clark St.) in the Wrigleyville neighborhood. This festival gathers the city’s finest wing-slingers showcasing their creations from classic buffalo and sweet-and-spicy to wood-smoked, jerk, and dozens of other unique flavors. Of course, wings aren’t the only thing on the menu. Live music, adult beverages, competitions, and more are all part of the package. After all, the chicken wing is the most patriotic food of all! Agree?
It’s back and bringing a taste of Germany with it! The 24th annual St. Alphonsus Oktoberfest returns this Saturday (12 p.m.-10 p.m.) and Sunday (12 p.m.-7 p.m.) to the Lakeview neighborhood. The intersection of Lincoln/Southport/Wellington is transformed into a Bavarian beer hall and packed with authentic German food, craft beer from local and international breweries, nonstop live oompah bands, stein-holding contests, polka dancing, and even a Kinderfest for the kiddos on Sunday. So, come dressed in your finest lederhosen and prost to one of Chicago’s most beloved fall traditions!
It’s time to welcome a brand-new music festival to one of Chicago’s most iconic streets. Clark Street Live is being held this Saturday (11 a.m.-10 p.m.) and Sunday (11 a.m.-9 p.m.) at 3500 North Clark Street from Addison Street to Newport Avenue in the Wrigleyville neighborhood. This festival features great live music on two stages with top tribute bands and country music, delicious eats from local restaurants and neighborhood bars, shopping, and more. Come and support this new event at one of Chicago’s most exciting entertainment destinations!
Adding another street fest to the mix this year, Middle Brown Bungalow introduces its inaugural Armitage County Fair this Saturday and Sunday (12 p.m.-10 p.m.) at 2840 West Armitage Avenue between California Avenue and Humboldt Boulevard in the Logan Square neighborhood. Get ready for an amazing time as this fair features an exclusive lineup of food and beverages; two stages of live music; comedy sets; contests such as a Governor Pritzker lookalike contest, hot dog eating, best dog dressed as a farm animal, and more; and plenty of family fun offering a petting zoo, a bounce house, face painting, and more. It sounds like this fair is a winner!
Another fall favorite tradition marking the beginning of fall is the St. Helen Carnival this Saturday (12 p.m.-10 p.m.) and Sunday (12 p.m.-9 p.m.) at 2347 West Augusta Boulevard in the Ukrainian Village. Enjoy 20 years of carnival fun at this free, family-friendly festival featuring carnival rides; music and entertainment; food and drinks; a beer garden; kids’ activities; and more!
Bringing together world-class jazz musicians, rising stars, and thousands of music lovers, the Hyde Park Jazz Fest will be held across multiple Hyde Park venues this Saturday (12:30 p.m.-10 p.m.) and Sunday (12:30 p.m.-7 p.m.). Enjoy an unforgettable weekend at Chicago’s South Side Serenade!
Sue Moss and Dean’s Team Chicago
