Even in the dead of winter, this beautiful rooftop bar at the Kimpton Gray Hotel feels like a tropical paradise. The menu here highlights South American flavors in drinks like the In the Morning, I'll Be Better, an addictive blend of plantain-infused Scotch, black walnut bitters, tiki bitters and smoke. Pair it with an order of the fan-favorite empanadas, which are stuffed with flank steak, red pepper and olives and served with chimichurri sauce.
On weekdays, the Loop is all business, but as soon as the clock strikes 5pm, downtown workers flock to the area's top watering holes for post-work tipples. The best bars in the Loop run the gamut, from swanky cocktail lounges and ritzy rooftop bars to the funkiest, oldest dives in town. And since most of these downtown bars cater to early-evening revelers, you can expect happy hour deals galore. Don't settle for a boring night of drinking downtown—dig into our guide to the best bars in the Chicago Loop.
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