48 Hours of Drinking in Chicago

Andy's Jazz Club draws a steady local crowd in River North. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Drop bags. Find a hotel-adjacent bar within a five-minute walk. Order something simple to anchor yourself to the city.

Cindy's Rooftop draws a steady local crowd in Loop. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. The polished room you'd take a first date to. Sit at the bar. Talk to the bartender. Stay one drink — you're scouting, not committing.

Headquarters Beercade draws a steady local crowd in River North. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Walk into the city's drinking quarter (the heart of the night, not the tourist version). Two drinks, two rooms. Pace yourself — Saturday is the long day.

The Aviary draws a steady local crowd in West Loop. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Sunset. Find a rooftop. Order whatever the house specials around sundown. Take photos but don't lose 90 minutes to your phone.

Bar Pastoral draws a steady local crowd in Lakeview. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Eat somewhere with serious bartending built in. The right room is one you order both your dinner and your nightcap from.

Bavette's Bar draws a steady local crowd in River North. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. The bar that made you book the trip. The pre-research one. Reservation-only ideally. Stay until last call.

Billy Sunday opened on Logan Boulevard in 2013 and is named after the early-20th-century evangelist who campaigned for Prohibition. The bar's response is to sto Mary, Mimosa, or whatever low-ABV house play the room runs. Eat. Pay. Walk.

Buddy Guy's Legends draws a steady local crowd in South Loop. Booking is recommended on weekends. Walk-ins are usually possible early in the evening. Find the hotel bar at your departure airport equivalent — somewhere quiet, low-volume, well-staffed. End the trip on a martini and a clean conversation.