Chicago has always been a great town for drinking, and that’s as true today as it’s ever been. The city is traditionally a blue-collar, beer-and-a-shot kind of town, and there are plenty of dive bars on this list. But there’s also a few innovative cocktail bars, thanks to the city’s emerging craft cocktail scene, and even a quirky tiki bar for island classics right in the middle of the Windy City. Whatever kind of watering hole you’re looking for, you’ll find something here. These are the best bars that every visitor to Chicago needs to check out.
1. Big Star
Big Star is a whiskey and taco bar in Wicker Park that’s the place to be on a beautiful day. The food is excellent, the drinks pair perfectly with the food and ambiance, and you can’t beat a table on the large patio watching the crowds walk by along Damen Avenue.
2. Lost Lake
If you like rum drinks and uber-cool bars, head to Logan Square’s Lost Lake tiki bar. The cocktails are some of the city’s best, and the Asian-inspired food menu will help soak up some of that booze.
3. Revolution Brewing
It’s not the first Chicago craft brewer, but Revolution Brewing is probably the biggest. The brewpub in Logan Square is a great place to eat and drink while watching the hip Logan Square crowd. You can also see some brewing going on if you’re fascinated by the craft.
Hopleaf is and always has been a north star for Chicago beer geeks. With domestic craft beers, obscure imports, and a focus on Belgian ales and food, Hopleaf never disappoints.
5. Parsons Chicken and Fish
Between Humboldt Park and Logan Square, Parsons Chicken and Fish fries up exactly what its name says it does, and it does it damn well. The huge patio is the place to be on a sunny day, and you can even play ping pong out there. The frozen Negroni slushy might be the best cocktail you can drink on a summer day in Chicago.
6. The Green Mill
No Chicago bar has more history than The Green Mill. It’s been around well over 100 years and was a Prohibition-era speakeasy. There are tunnels in the basement that allowed the bar to smuggle in booze and let gangsters like Al Capone escape during police raids. Today, it’s one of the city’s best jazz bars.
7. The Continental
When most of the near Northwest Side bars close at 2:00 AM, drinkers head to The Continental to keep the party going until 4:00 AM (5:00 AM on Saturdays). Like all late-night bars in the city, it can get a bit sloppy, but the drinks are good, the music is great, and at that hour you don’t have many other choices, anyway.
8. Twisted Spoke
Twisted Spoke is a biker bar that’s softened its edges up a bit but still gets plenty of motorcycle riders coming in. It does pub grub very well and has a great weekend brunch. Everything on the impressively large whiskey list is half price on the bar’s famous Whiskey Wednesdays.
9. The Kedzie Inn
There are few things more Chicago than the neighborhood sports bar, and The Kedzie Inn is this writer’s favorite one. It’s a great place to catch a game, plus it has pool, darts, ping pong, and old-school video games on an old tube TV. The food rocks, too.
10. L&L Tavern
The L&L is definitely the diviest bar on this list. It is a literal hole in the wall, and it’s great. There’s not much to say about it other than it’s a nice place to get a drink, although serial killers John Wayne Gacy and Jeffrey Dahmer are both rumored to have hung out there.
11. Old Town Ale House
Old Town doesn’t have many dive bars left, but it still has one gem. Old Town Ale House is a classy dive and a great place to get a drink. Performers from the nearby Second City comedy club often stop by late and always bring the laughs.
On the near Southside along Halsted Street, on the eastern edge of Pilsen, Skylark is a fantastic neighborhood bar that you can’t help but fall in love with. It’s divey, but the food and drinks are great, and the regular crowd is friendly. Oh, and it has a photo booth.
13. Murphy’s Bleachers
Wrigleyville with its bro culture probably has more terrible-to-mediocre bars than anywhere else in the city, but there’s no denying it’s fun to go and drink around there when there’s a Cubs game going on. If you’re not in the stadium, the place to be is Murphy’s Bleachers. It’s one of the classic bars of the neighborhood, and it’s literally across the street from Wrigley Field’s bleacher gate.