Boleo

"Happy hour is a big draw for the Kimpton Gray Hotel’s rooftop restaurant, with Financial District workers stopping in for pisco cocktails, ceviche and yucca fries. The Latin American-inspired dinner menu features empanadas, lomo saltado and flan, with the retractable roof ensuring the tropical getaway isn’t interrupted by Chicago weather. Make a reservation through OpenTable." - Samantha Nelson

"Chicago’s mercurial weather patterns meet their match at Boleo, a South American rooftop lounge and restaurant with a retractable glass roof atop the Kimpton Gray Hotel. Designed to create the feeling of al fresco hospitality regardless of precipitation, it specializes in colorful, crowd-pleasing drinks like Passion Puma (Vida mezcal, jequitiba rosa, guava) and Two to Tango (Plantation rum, Giffard banana, Dolin Blanco, huna, melon). Balance out the booze with cevices, empanadas, and large plates like bone-in grilled pork chops." - Naomi Waxman, Ashok Selvam

"Peruvian street food inspired the menu at this Loop rooftop bar, which offers chicken empanadas spiced with panca peppers and served with a side of aji amarillo, a spicy and creamy green sauce. A vegetarian version combines kale, provolone, and cremini mushrooms and comes with romesco sauce." - Samantha Nelson, Ashok Selvam

"It's not often you can feel immediately transported, but walking into Boleo, with its retractable roof and collection of exotic palms, makes it seem you've stepped off a plane in Buenos Aires. It has a lively, upbeat atmosphere—so go ready for the party vibe." - Nicole Schnitzler

"Empanadas and Fernet and colas help diners pretend that the weather’s warm. Plus, the rooftop’s skylight of this swanky Latin spot lets in just the right amount of sun to feel warm even if it’s freezing outside." - Naomi Waxman