25 bars · checked November 2026
Twenty-five bars across the Loop, West Loop, River North, Logan Square and beyond that we'd actually send a friend to, each one checked open this month, with nights that string them together on foot.
If you only have one night
Bars in an order that works
Any night · 3 stops · all walkable
Start in the Alinea Group's cocktail lab, drop downstairs into the speakeasy underneath it, then finish three blocks over at the most decorated bar in the city.
One floor down: a 21-seat speakeasy, key-access, vintage spirits.
One floor down.
Any night · 3 stops
Amaro first, then the city's deepest gin list, then a wine nightcap in a room built like a mountain inn.
Walk the boulevard to one of the city's largest gin collections.
About 10 minutes on foot.
Close on a glass of something European and a plate of schnitzel.
About 10 minutes on foot.
Any night, best on a warm one for the patios · 3 stops
A gas-station taco bar, a hidden craft cocktail room, then a photo booth with 40 years of regulars behind it.
A quieter cocktail room behind the comic-book storefront window.
About 7 minutes on foot.
By neighbourhood
Fulton Market's old meatpacking blocks, now Chicago's most decorated kitchens and its most ambitious cocktail bars.
3The city's densest stretch of hotel bars and basement speakeasies, plus a 200-rum tiki room down an alley stair.
7Boulevard bungalows and a bar strip on Armitage and Logan, where amaro, gin and Alpine wine each have a bar of their own.
3Quiet brick blocks west of Wicker Park, best known here for the bar Chicago's own bartenders drink at on their night off.
1Skyscraper canyons and a river bend, with two rooftops looking down on Millennium Park and the bascule bridges.
2Clark Street's long-running neighbourhood strip, home to a 300-bottle whiskey room that feels like somebody's parlour.
1Murals, taquerias and an agave-and-vinyl patio, one of the best heated hangouts on the Southwest Side.
1Milwaukee Avenue's bar row, from a gas-station taco honky-tonk to a cash-only dive with a photo booth older than most of its regulars.
3The lake side of the Mag Mile, anchored by the world's largest rooftop bar out over Navy Pier.
1Walton Street's old-money blocks, led by a bar that's poured Martinis since the day Prohibition ended.
1Comedy-club blocks around Second City, with a 1958 dive whose walls are the real draw.
1A warehouse strip west of the river, home to one of the narrowest bars in the city.
1Good to know
For a special occasion, Kumiko or The Aviary in the West Loop, both among the most decorated bars in the country right now. For a deep spirits list without the ceremony, Billy Sunday (amaro) or Scofflaw (gin) in Logan Square.
Kumiko, The Aviary and The Office require one, booked well ahead. The Berkshire Room, Scofflaw and Cindy's Rooftop are much easier with a booking. Rainbo Club, Old Town Ale House and The Matchbox are walk-in only.
The Office, a 21-seat key-access room below The Aviary (West Loop); The Drifter, down a stair under the 1872 Green Door Tavern, and The Franklin Room, both in River North.
Three Dots and a Dash, The Berkshire Room, Celeste, Pop's for Champagne, The Drifter, The Franklin Room and Bar Sótano are all within a few blocks of each other in River North.
Most close at 2am, 3am on Saturdays under the city's late-hours license; a few, like Old Town Ale House, stay open to 4 or 5am. The L runs all night on weekends, but a cab or rideshare is the easier way home after 2am.
Every bar here was checked against its own site or listing in November 2026. Bars change hours and menus often, so check before a big night.