There’s not much better than sipping a cocktail in the sun while taking in expansive Chicago vistas. At London House’s iconic rooftop, you can look down at the city with a quintessential LH Old Fashioned in hand, packed with Bulleit Bourbon, rum barrel-aged maple syrup, orange, and angostura bitters. Don’t skip the bar snacks, either. LH is serving up some fusion dishes that are hard to miss, like gochujang mole beef ribs and bulgogi beef nachos. 

This meat market from internationally renewed chef/philanthropist José Andrés has all your carnivorous bases covered, which in Chicago is certainly saying something. Cotton candy foie gras and Philly cheesesteaks share the stage with caviar service and all manner of decadent Japanese steaks prepared on an ishiyaki grilling stone. As for booze, you can’t go wrong with the Bazaar Old Fashioned mixed with Bulleit Bourbon, Torres 15-year brandy, infused orange, chamomile, and angostura bitters.

This swanky outpost of the Viceroy Hotel hits home runs with its Maine lobster burgers, King Crab crispy rice, and housemade agnolotti and orecchiette, but its drinks department is reason enough to go. Order The Dean (Bulleit Bourbon, clarified milk punch, pinot noir) from their feisty celeb-inspired cocktail list and settle into a deep blue booth. On select Sundays, you can even bring your pup with you. 

This award-winning hotel continues to wow guests with an upscale yet approachable assortment of dining adventures, from the English room (with a wine list voted one of the most outstanding in the world) to the more laid-back White Hart Pub, serving up classics like chicken pot pie and fish and chips. You’ll have no shortage of drink options to go alongside the cozy fare, including the Boulevardier made with Bulleit Rye, Campari, vermouth, and bitters.

Longtime locals have been madly in love with this quirky riverside spot for generations. Give a beautiful day on the river the ultimate sendoff with a Bulleit Old Fashioned (Bulleit Rye, sugar cube, muddled orange, cherry, and angostura bitters) paired with a dish from their seafood-heavy menu, like a bucket of clams or mussels, fried oysters, steamed Alaskan crab legs, or jumbo sea scallops with beurre blanc.