Head to State Street to celebrate Halloween as the "artist's holiday" with an evening of wonder and creativity at the Arts in the Dark Halloween Parade on October 24, 2026, in the Loop. Recognized as one of the top six Halloween events in the world, the tenth annual Arts in the Dark parade … [Read more...] about Arts in the Dark Halloween Parade
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Free and cheap perks on National Coffee Day 2026
Cream and sugar, please? Everyone will definitely be buzzin’ with excitement (and caffeine!) on National Coffee Day, Sept. 29, 2026, thanks to these cheap perks for coffee lovers and bargain hunters alike. To stir things up for the day, many coffee shops are celebrating the day with freebies and … [Read more...] about Free and cheap perks on National Coffee Day 2026
Chipotle celebrates National Quesadilla Day with free quesadilla for two days
National Quesadilla Day is so cheesy! And Chipotle is celebrating National Quesadilla Day with a big, cheesy giveaway for two days — Sept. 24 and 25, 2026. The popular restaurant’s quesadillas feature melted Monterey jack cheese, a choice of protein, optional fajita veggies and multiple sides for … [Read more...] about Chipotle celebrates National Quesadilla Day with free quesadilla for two days
Reeling International Film Fest
The second-oldest LBTGQ+ film festival in the country kicks off with an exciting line-up of international features, documentaries and shorts with the 44th annual Reeling International Film Festival on September 17-27, 2026. The rich diversity of the queer community is showcased during the … [Read more...] about Reeling International Film Fest
Enjoy free bucket of chicken wings at KFC this football season
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
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
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
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
Labor Day weekend freebies and deals 2026
Many restaurants are offering Labor Day discounts and freebies, perfect for those who don’t want to cook over the holiday weekend. Some of the deals are only valid on Labor Day, while others have varying promo dates. Click on the link in each item for more details. Capital One … [Read more...] about Labor Day weekend freebies and deals 2026
Ravenswood ArtWalk
The Ravenswood Corridor community celebrates 24 years of the annual Ravenswood ArtWalk on September 12-13, 2026. The area's artists, manufacturers and brewers will welcome visitors during the ArtWalk with a host of fun and interactive activities. Unfolding from Lawrence to Irving Park St.. … [Read more...] about Ravenswood ArtWalk
Free Printers Row Lit Fest
The Midwest's largest literary festival returns to Chicago's historic Printer's Row neighborhood in the South Loop with the Printer's Row Lit Fest on September 12 and 13, 2026. Stretching out over five blocks, the Printers Row Lit Fest features more than 100 booksellers, interactive … [Read more...] about Free Printers Row Lit Fest
German-American Oktoberfest
Celebrate German heritage in all its forms, including dance, music, and food at the annual German-American Oktoberfest on September 11- 13, 2026, in the Lincoln Square neighborhood. The opening ceremony kicks off at 8 pm on September 11. Commemorating 100 years of German traditions, the … [Read more...] about German-American Oktoberfest
