The Best Food-Drinks Events in Chicago This Month

If you’ve been trying to make dinner plans and keep getting derailed by someone saying, “Wait, there’s this thing tonight…,” welcome to the current reality of food-drinks events in Chicago. The city’s in full-going-out mode, and people aren’t just talking about it—over 1,600 Chicagoans are already RSVP’d or circling this week’s highlights alone. If you’re looking for the best food-drinks in Chicago this month, it’s less about finding *something* to do and more about choosing which excellent option you’re okay missing.

Right now, the energy is very: bundle up, grab a friend, and pretend it’s not that cold as long as there’s something good in your glass or on your plate. WinterFest – An Outdoor Winter Celebration is basically that vibe in event form: parkas, hot drinks, and the annual test of how long Chicagoans can stand outside for the promise of snacks and seasonal cheer. If you’re more of a “fed and entertained” person, the Annual Real Men Cook Chicken & Chili Cookoff has serious comfort-food energy—big flavors, bigger bragging rights, and the kind of crowd that turns a tasting into a full-on hang.

On the more street-level, hyper-local side, the 47th Street Taco Crawl II is the one you text your group chat about immediately. It’s got that classic South Side crawl energy: low-key chaotic, taco in one hand, phone in the other, trying to decide which spot deserves a return trip next weekend. In the South Loop, Mariano’s is going harder than your average grocery store with its Lunar New Year Celebration—think lion-dance-adjacent vibes, festive bites, and a reason to pretend your weekly shop is suddenly cultural research. Then there’s Vincent Massacre 50th edition and YAM Game Night, which lean more into hangout territory: think drinks, familiar faces, and the kind of night that accidentally runs late.

The venues holding a lot of these moments together are the usual suspects for a reason. Eataly Chicago is still that place where you “just stopped in for one thing” and somehow end up at a tasting, a class, or parked at a counter with a glass of wine and no regrets. WineStyles Chicago is for when you want to feel like a regular even if it’s your second time there—tastings, flights, and the kind of cozy, slightly chatty energy you don’t get at a massive bar. And spots like 1806 W Cuyler Ave are where the city’s smaller, weirder, more personal gatherings live—the game nights, niche pop-ups, and friends-of-friends events that end up being the stories you tell later.

If you want to actually make the most of Chicago’s food-drinks scene right now, here’s how to play it: book the bigger, once-a-year things first (the cookoff, WinterFest, the taco crawl), then layer in the lower-key hangs like YAM Game Night or a tasting at WineStyles. Use Eataly as your “we don’t know what we’re doing but we want it to be good” fallback. This is what discovery looks like in Chicago right now: a mix of classic names, neighborhood experiments, and the constant feeling that the best thing you went to this month wasn’t even on your calendar 24 hours before.