The Time Out Chicago blog team

Whether you’re ready or not, summer is coming to a close. It’s been a busy one, filled with monumental moments like the Obama Presidential Center opening, America’s 250th anniversary, WNBA All-Star Weekend, and so much more. But Labor Day weekend is here, and it’s finally time to say goodbye to summertime Chi. With a sunny (for now) forecast predicted over the next few days, it’s only right to get out and make the most of the coveted three-day weekend and celebrate what the national holiday is all about: celebrating the contributions of the American worker. Ready to send summer off with a bang? Here are our picks of the best events and things to do over the long weekend. For our full guide to more than 40 things to do this weekend, click here. RECOMMENDED: The 16 best bars for day drinking in Chicago 1. Chicago Labor Day Parade & Eddie Fest The Chicago Labor Day Parade returns to historic Pullman on Saturday. Organized by the Chicago Federation of Labor, the event celebrates union pride, solidarity and community togetherness. The parade will step off at East 112th Street and South Avenue F on the Southeast Side, before continuing north up South Ewing Avenue to East 106th Street. Afterwards, stick around for Eddie Fest, featuring live music, food and family-friendly activities, at Steelworkers Park.  2. Chicago Jazz Festival As is Labor Day weekend tradition in Chicago, some of the biggest names in jazz will gather for a series of shows through Sunday at Pritzker Pavilion...

Chicago’s biggest celebration of Mexican culture returns to Grant Park, and it’s bringing a seriously stacked lineup with it. After taking off 2025 due to then-impending immigration enforcement actions, El Grito Chicago returns September 12 and 13 with two days of music, food, dancing, family activities and enough tacos to make you finally understand the concept of eating enough tacos. The festival’s 2026 headliner is Sinaloa-born singer-songwriter Adriel Favela, one of the major names in the new wave of regional Mexican music. He’ll be joined by Código FN, the legendary technobanda group Mi Banda El Mexicano, rising singer Emmanuel Cortés and Chicago’s own Latin Grammy-nominated Mariachi Herencia de México. The lineup also includes Selena The Show, a tribute to the late Tejano superstar; Chicago group Los de La Homan; a live Juan Gabriel tribute; band Sin Anestesia; sierreño group El Ejercito Sierreño; and the Kombi Bus Dancefloor, a DJ-and-dance experience. RECOMMENDED: The 38 best Mexican restaurants in Chicago, whether you're craving tacos or a steaming bowl of pozole Photograph: Courtesy El Grito ChicagoEl Grito Chicago And because no Mexican party worth its salsa should be expected to survive on music alone, El Grito is bringing along a formidable roster of Chicago food vendors. Cafe TOLA, Prime Tacos, Xurro, Fernando’s Blue Agave, Bust Outs, Banges, J’s Bacon Hot Dogs, Tacos El Rey, Carnitas Roldan, La Cebollita Grill, El Taconazo Express, Paleteria Los Magos,...

Chicago's dining scene has scored another big bragging right to add to the city's ever-growing list. John’s Food & Wine, the intimate Lincoln Park restaurant from chef-owners Tom Rogers and Adam McFarland, has officially been named the 2026 Restaurant of the Year by Food & Wine.  The honor, announced on September 1, recognizes restaurants that are helping shape the future of American dining through exceptional food, hospitality and impact. And while John’s certainly has the cooking chops, it’s the way Rogers and McFarland have structured their business that makes the restaurant especially notable. RECOMMENDED: This West Loop bistro was just named one of America’s best new restaurants by Bon Appétit, and their roast chicken is perfection View this post on Instagram A post shared by Food & Wine (@foodandwine) Rogers and McFarland met in Chicago almost 20 years ago, eventually working together at New York’s Gramercy Tavern under chef Michael Anthony before returning to Chicago and opening John’s Food & Wine (named after their fathers) in 2024. In addition to building a business together, they also literally built much of the restaurant, including the bar. But the most radical feature of John’s Food & Wine isn't on the plate. Every guest pays a flat 20-percent hospitality charge, which is pooled among the front- and back-of-house staff, while employees earn at least $25 an hour. Workers can also boost their earnings by taking on additional...