I almost titled this post Best Cocktails in Chicago, then thought twice. Taste is subjective, and I’m not here to pretend I’ve sampled every gin-forward negroni in the city. (Spoiler: I probably skipped those.)
If you’re a tequila, bourbon, vodka, or whiskey kind of person – you’re in the right place. These are some of the most memorable cocktails I’ve encountered around Chicago. No gimmicks, no over-the-top garnishes, just fun, interesting drinks.
Bottoms up.
Gochu-Melon Rita – Mott St.
Granted, it’s on the seasonal cocktail menu, but I loved it so much I’m hoping it earns a year-round spot. Mott St.’s summer spin on a margarita mixes tequila, mezcal (because why pick just one?), Korean chili, and watermelon. It’s as refreshing, and as fun, as it sounds.
Union Old Fashioned – Union
Dare I say, my favorite Old Fashioned in the city? Perfectly balanced, deeply boozy, and served in a space that makes you want to order a second and cancel whatever plans you had next.
Green House – Eden
Eden’s seasonal menu leans into fresh, local flavors, many of which are grown steps away in their on-site greenhouse. So naturally, ordering the ‘Green House’ cocktail is a no-brainer. The martini-style cocktail checks every box: citrusy, refreshing, and sneakily strong. I sipped it on a rare 75-degree April day and found myself daydreaming of warmer months ahead.
Cloud Hopper – Kumiko
Ranked #10 on the 2025 North America 50 Best Bars list, Kumiko clearly knows its way around a cocktail. So if there’s ever a place to step outside your usual order and try something totally unexpected, it’s here. The Cloud Hopper caught my eye with its description: buoyant, colorful, rich, and fruity, and it delivered on all counts.
The cocktail is made with Chiyonosono ‘8000 Generations’ rice shochu, mezcal, passionfruit, green cardamom, oat milk, Yakult, and lemon — a lineup that sounds more like a riddle than a recipe. I couldn’t tell you what half of those ingredients actually taste like on their own, but together, they work.
Lychee Martini – Le Colonial
There are plenty of reasons to book a table at Le Colonial: the French-meets-Vietnamese cuisine, the lively decor, and let us not forget, the people-watching. But the lychee martini deserves its own moment. It’s perfectly chilled, not overly sweet, and better than Nobu’s (yes, I said it).
The Daiquiri – Mirra
This isn’t your average daiquiri – but in the best possible way. Mirra’s version mixes rum with chai, kiwi, and, surprisingly, avocado. I hesitated for a second (as one does when faced with avocado in a cocktail), but curiosity and a very convincing bartender convinced me to give it a try. Much like the food menu, the drinks here lean bold and unexpected in all the right ways. If you go, don’t miss the Roasted Bone Marrow Tacos or the Lamb Biryani. Trust me.
Espresso Martini – Gemini
No espresso martini on the menu? No problem. Gemini’s bartenders will still make you one anyway, and you’ll be glad they did. Made with fresh espresso (no syrupy, faux-coffee liqueur here), vodka, and a mystery something I can’t quite place, this martini is smooth, rich, and balanced. You can’t go wrong with brunch at Gemini, and their espresso martini further proves that point.
Oaxacan Old Fashioned – Trivoli Tavern
Trivoli’s Oaxacan Old Fashioned is a bold, smoky twist on a classic. They swap bourbon for Oaxacan blanco tequila, and somehow, it works. If you’re a tequila person, or just looking to break out of your usual Old Fashioned rut, this one’s worth a sip. A rare exception to the “if it ain’t broke, don’t fix it” rule.
Envy Looks Good on You – Cindy’s Rooftop
There’s something about a jalapeño cucumber cocktail that always grabs my attention, especially on a 97-degree summer afternoon. “Envy Looks Good on You” is a tequila-based sipper with jalapeño, cucumber, dill, and lemon, served over ice. A touch sweeter than I usually go for, but it’s hard to complain when your cocktail comes with a skyline chaser.
Have any favorite cocktails in Chicago that I missed? Let me know!