Diego Chicago Restaurant | Dinner, Late Night, Weekend Brunch

Diego Chicago strikes the perfect balance between neighborhood joint and destination dining. The patio is where the magic happens—string lights sway overhead while local bands set the soundtrack for your evening cocktail ritual. Their mezcal-forward drinks deserve your attention, especially the smoky margarita that somehow tastes like vacation in a glass.

The food punches well above typical outdoor drinking fare—those empanadas have developed their own cult following for good reason. While weekend brunches draw crowds (arrive early or prepare to wait), weekday happy hours offer the sweet spot of atmosphere without the hustle.

Yes, street parking can be a minor headache, but that's Chicago for you. The staff remembers regulars and treats newcomers like they might become one. Dog owners, rejoice—your four-legged friends are not just tolerated but celebrated with water bowls and the occasional treat. When the temperature drops, those patio heaters work overtime, extending outdoor season well into Chicago's fickle fall.