Unique Bars in Chicago

Chicago has every kind of nightlife you'd expect from a big city: dive bars, gay bars, hotel bars, beer bars, rooftop bars and dance clubs. The bars below are the ones with a hook. A jazz room where the owner will shush you, a tiki basement you reach through an alley, a burger counter under Michigan Avenue. Every one of them was open as of September 2026, and most have been around long enough that they aren't going anywhere soon.

A few changes since we first wrote this list. The Violet Hour, the unmarked Wicker Park speakeasy that led the original version and helped start Chicago's craft cocktail boom in 2007, closed for good in June 2025 after building damage and a dispute with the landlord. The owners have hinted it could come back somewhere else, but there's nothing concrete. Blue Stem, the Lincoln Square martini bar where the owner would refuse your order and make you something better, is also gone.

The Green Mill

The Green Mill at 4802 N. Broadway in Uptown is the one bar on this list we'd tell anyone to go to. City records put its opening in 1898, though you'll usually hear 1907, and in the 1920s "Machine Gun" Jack McGurn of the Capone outfit was part-owner. The curved booth people call Al Capone's booth is a nice story, but the current room didn't exist until 1935, three years after Capone went to prison. Dave Jemilo took it over in June 1986 and the club marked 40 years under him this summer.

Come for the music, not the conversation. Staff will tell you at the door to silence your phone and keep quiet during sets, and Jemilo himself is known as the house shusher. It's cash only (there's an ATM), there are no reservations and no food, and cover depends on who's playing. It stays open until 4am on Fridays and 5am on Saturdays, with a $5 cover after 1am on those nights. On Sunday afternoons you might catch the Uptown Poetry Slam, which started here in 1986. The rebuilt Lawrence Red Line station, which reopened in July 2025, is a block away. For more live music, see our guide to blues and jazz clubs in Chicago.

The Book Cellar

A bookstore isn't a bar, but the Book Cellar at 4736-38 N. Lincoln Ave. in Lincoln Square pours wine and beer in its cafe alongside sandwiches and pastries, and that's enough for us. It's been an independent, woman-owned shop since 2004, with a sharp staff picks shelf and a busy calendar of author events and book clubs. Hours are 10am to 8pm on weekdays, 10am to 6pm on Saturday and 10am to 4pm on Sunday, so this is an early-evening glass, not a nightcap. The Western Brown Line stop is a short walk away.

CloudBar at 360 Chicago

The Signature Lounge on the 96th floor of the old John Hancock Center was our pick for a drink with a view. It closed in September 2023, and the building now goes by its address, 875 North Michigan Avenue. The replacement is two floors down. CloudBar sits on the 94th floor inside the 360 Chicago observation deck, and 360 Chicago now bills it as the highest cocktail lounge in the city. The difference is that you need a deck ticket to get in. General admission starts at $30 for adults, and the Sip & View ticket, from $44, includes one drink or snack. The deck is open 9am to 11pm with last entry at 10pm. Go about an hour before sunset and stay while the lights come on.

If paying admission for a cocktail bothers you, Cindy's on the 13th floor of the Chicago Athletic Association hotel, 12 S. Michigan Ave., looks straight over Millennium Park to the lake and costs nothing to walk into. There's a glass atrium, so it works year-round. Reservations open 14 days out, and walk-ins are welcome.

Kumiko

Julia Momosé opened Kumiko at 630 W. Lake St. in the West Loop in 2018, and it has since collected Outstanding Bar at the 2025 James Beard Awards and a 10th-place spot on North America's 50 Best Bars in 2024. It calls itself a Japanese dining bar, and the food gets the same care as the drinks. The name comes from a Japanese woodworking technique of latticework fitted together without nails, which you'll see in the room. The bar is open Wednesday to Sunday, 5pm to midnight, and books through its website. It's about a block west of the Clinton Green and Pink Line stop.

Three Dots and a Dash

Look for tiki torches in the alley behind 435 N. Clark St. in River North. That's the entrance to Three Dots and a Dash, a basement tiki bar that opened in 2013 and reached 13th on The World's 50 Best Bars the following year. A doorman lets you in and you head down a dark staircase lined with skulls. The drinks are rum-heavy and built on the classic tiki recipes of the 1930s to the 1970s. The name is Morse code for V, for victory, taken from a World War II-era cocktail. It opens at 4pm most days (2pm on Saturdays) and takes reservations on OpenTable, which you'll want on a weekend. It's 21 and over.

The Aviary

Grant Achatz and Nick Kokonas, the team behind Alinea, opened The Aviary in 2011, and it won the James Beard award for Outstanding Bar Program two years later. It's at 955 W. Fulton Market, and it's the fanciest stop on this list, with food and non-alcoholic pairings as well as cocktails. Book through Tock rather than hoping to walk in. Its sister bar, The Office, sticks to classic cocktails and vintage spirits.

Delilah's

Mike Miller opened Delilah's at 2771 N. Lincoln Ave. in 1993 and says it has been open every day since. It's a punk bar with one of the country's great whiskey shelves, over 1,000 beer and spirit options in all, and in 1995 the Louisville Courier-Journal named it the best whiskey bar in the world. DJs play punk, metal, soul, rockabilly and hard country, and there are film screenings and art openings too. It's open until 2am most nights and 3am on Saturdays. If you're spending the day in Lincoln Park, this is where it should end.

Old Town Ale House

Roger Ebert called the Old Town Ale House "the best bar in the world that I know about," and Anthony Bourdain brought his CNN show here. It's been open since 1958 at 219 W. North Ave., at Wieland. Owner Bruce Elliott, a regular since 1961, inherited the place on the condition that it not be changed, and has covered the walls with his paintings. Some are portraits of regulars and of Second City alumni like Bill Murray and John Belushi, and some are political satire that has landed him in the news. There's a jukebox and a pinball machine. It's cash only, opens at 3pm and stays open until 4am (5am on Saturdays), which makes it a good last stop after a show in Old Town.

Billy Goat Tavern

Take the stairs down from Michigan Avenue to 430 N. Michigan, Lower Level, and you're in the Billy Goat Tavern. Billy Sianis opened the first one on West Madison in 1934 and moved to this spot in 1964, where it became the hangout for newspapermen, Mike Royko among them. Sianis is the man who brought his goat to the 1945 World Series, got thrown out and put a curse on the Cubs that held until 2016. John Belushi's "Cheezborger, cheezborger" sketch on Saturday Night Live is usually traced to the place, though Dan Aykroyd has said it was based on another diner. Order a double cheezborger and a beer, don't ask for fries, and sit at the bar. It's more burger joint than bar, but no list of Chicago drinking spots feels right without it.