There’s no shortage of wine events in Chicago. But every now and then, one stands out not because it’s the biggest or flashiest, but because it simply gets everything right. This year’s Chicago Gourmet’s Grand Cru, held on September 27th, 2025 at the Harris Theater rooftop in Millennium Park, was one of those nights.

From the moment we stepped onto the rooftop, the city was putting on a show. The skyline stretched out as a perfect backdrop.  There was music, laughter, and that unmistakable sound of wine glasses clinking the kind of energy that makes you instantly glad you showed up. The space was organized beautifully. No long lines, no elbowing your way to a table just a relaxed rhythm that let you move from one station to the next, tasting, talking, and taking it all in.

The wine line-up was something special. 2019 Caymus Vineyards Special Selection Cabernet Sauvignon, 2021 Justin Isosceles, 2023 Rochioli Estate Russian River Chardonnay, and 2021 Ehlers Estate Cabernet Sauvignon 1886 were among the highlights, and each one brought its own personality to the evening. Caymus poured with rich confidence and finesse, filling the glass and lingering for minutes. Justin showed off balance and structure, especially in their iconic Isosceles blend, which had this elegant, layered depth. And then there was the Rochioli Estate Chardonnay, easily the standout for us as well with its tapered citrus fruits and creamy, rich background. 

What made these tastings really memorable wasn’t just the wines themselves, but the people behind them. You could tell these weren’t just brand representatives reading from a script. They talked about vintages, soil, harvest conditions, even specific barrels and the quirks of each season. It gave the wines context, made them feel alive. It reminded me that wine is storytelling in liquid form you’re tasting someone’s work, their patience, their gamble with nature.

And then there was the food. Chicago’s best chefs and local favorites showed up in style with creative small plates that actually fit the wines being poured. Everything just flowed. The staff was on point, the pacing was easy, and everyone there seemed to be having a genuinely good time. It didn’t feel like an exclusive tasting, it felt like a gathering of people who simply loved wine and food. 

At one point, I just stopped and looked around. The city lights were glowing, the skyline framed by glasses and conversation, and it hit me how rare it is for an event to feel this refined, but not stuffy, upscale but still comfortable. Chicago Gourmet Grand Cru managed to hit that sweet spot perfectly.

By the end of the night, my notes were messy, my palate was happily exhausted, and I knew I’d just been part of something worth remembering.Chicago Gourmet Grand Cru isn’t about chasing prestige or checking boxes it’s about connection. The people, the wine, the food, and the city all came together in a way that felt effortless and real.

If you love wine, great food, and the energy of Chicago when it’s at its best, this is the event to mark on your calendar. You leave with more than a list of wines you liked you leave with stories, a few new favorites, and a reminder of why we raise a glass in the first place.

Chicago Gourmet 2026 will be held from September 24-27, 2026. Information and tickets can be found on their website at www.chicagogourmet.org/page/ticketsales.

Tacos & Tequila

A Celebration of Agave and Artistry on Chicago’s Streets

A few nights earlier, the mood shifted same city, totally different vibe. The Tacos & Tequila Festival felt like Chicago cutting loose. Gone were the tasting notes and quiet nods of approval, this was all energy, flavor, and fun. The air was thick with the scent of grilled meats, roasted peppers, and fresh lime. Everywhere you looked, people had tacos in one hand, a tequila cocktail in the other, and a grin that said they were exactly where they needed to be.

The tacos themselves ran the full spectrum; smoky al pastor, slow-cooked short rib, crispy fish with a hint of crema, even a vegan option that held its own. The standout? perfectly cooked tacos from 5 Rabanitos and alongside multiple rounds of gran Centenario cocktails. 

What was great about this event was that the tequila wasn’t just an afterthought. It was a showcase with a few surprises in the mezcal corner for those chasing smoke.

Different from the Grand Cru in every possible way, yet just as memorable. Where Grand Cru was wine focused, Tacos & Tequila was relaxed, a reminder that good drinks and great company come in many flavors.