Drink This Winter Bourbon Smash and Conquer Cold Weather Forever
Whether you’re shooting pool, listening to weird old men rock out during open mic night, or staring at the giant Mona Lisa on the wall or Elvis by the door, you’re going to have a good time at Innertown. Mingle with neighborhood locals while smoking butts by the bike rack outside for the full Innertown experience.
2. Burton Place
The best part about late nights are the inevitable bad decisions they bring with them. And the best bad decision you can make is a trip to Burton Place where, despite three levels of drinking space, you will DEFINITELY run into at least two people from high school. Guaranteed.
Are you the type that takes ping pong so seriously you carry around your own custom paddle? If so, Happy Village and its back ping-pong room is the place for you. If not, the spacious outdoor garden (which, for the record, is not as spacious since they constructed the tent) is one of the best things about living in Chicago. Hands down.
While Logan Square has devolved into an endlessly looping cycle of new bars and restaurants, few places are as fun or as beloved as Slippery Slope. And if you can’t pick up babes on the skee-ball court, where the hell can you?
5. Violet Hour
Impress the hell out of your date as you spot the nondescript wall which hides some of the finest cocktails in America.
Schubas is a perfectly delightful old-time Schlitz bar whose back room has just happened to host some of the best bands in Chicago for decades. You can go here and be quite content ordering Green Line on draft bellied up to the bar and chatting up locals. Or you can head in back and slam dance in your button-down. Either way works.
7. Empty Bottle
Chicago’s finest live music venue is also one of its finest hipster bars. If you’ve been here (and if you’re the type that likes to shoot pool with the dudes from Interpol), you know why.
8. Tai’s Til 4
Tai’s may be located within close proximity to the Friendly Confines, but there’s nothing friendly about the dead-eye gaze from the meatheads who pack this place. Ignoring them and managing to have a good time regardless results in a feeling of accomplishment all Chicagoans should experience.
The best reason to visit the South Loop isn’t to dial up Orange Is the New Black with your married friends in their sweet new condo. It’s Reggies, where punk bands, killer bar food, a party bus to Bears games, and the "Trainwreck" rooftop deck conspire to create a bucket list-worthy experience.
The thing about Nick’s? It’s a perfectly reasonable neighborhood bar before 2am. After 2am? All bets are off, and you best find yourself a table in this suddenly packed space unless you’re really into uncomfortable shoulder rubs with strangers. Pro tip: get there early and grab a spot in the cozy little back patio, aka the “beer garden.”
11. Moody’s Pub
Brendan Sodikoff’s recent revamp may have brought a bit more sparkle, but the old-school charms and ubiquitous red-light vibes of this standout cocktail lounge remain the neighborhood’s number one draw card for booze.
13. Green Mill
It’s one of the oldest bars in Chicago. It’s the best bar in Uptown. It’s the most iconic bar in Illinois. It’s also one of 35 things to do in Chicago before you die. So what the hell are you waiting for? An invite to the reputed secret mobster tunnels under the bar?
Nudie paintings of Palin and Blago may get all the attention, but sitting here in the middle of the day grousing about politics with grizzled old-timers is one of finest pleasures in the entire city of Chicago.
If standing in line for a comically small bathroom is on your bucket list, Estelle’s is the place to emphatically cross that one off. On the plus side? The place is so small you are practically forced to talk to people, which is actually how hookups used to happen before Tinder and Grindr. And if you score a table, consider yourself a god.
One of America’s finest cocktail bars will make a gin lover out of even the most gin-averse of clientele. Just order anything and it’ll be good. And it’ll be even better when sipped on a funky antique sofa near the window.
17. Billy Sunday
18. Barrelhouse Flat
Barrelhouse Flat stands out from its Lincoln Park brethren simply by virtue of not being terrible. But look beneath the surface and you’ll see one of Chicago’s most beautiful bars as well as one of the best places for getting smashed in the wee hours. A late-night crowd that can actually handle its booze? This you gotta see.
19. Kingston Mines
Like partying with an oddball mix of tourists, college kids, and scraggly old blues dudes? Then you’ll love Kingston Mines, where this weird mix of energy is actually one of the bar’s finest assets. If you wanted to go to any other interchangeable bar, you’d go almost anywhere else in the neighborhood.
Underbar gave us all quite a scare by announcing its closing last winter. But spring brought with it the return of Chicago’s finest late-night institution. Have people here had a few too many? Of course. Are they puking on your shoes and trying to fight you? No. And therein lies the difference.
21. The Owl
For a neighborhood as bar-heavy as Logan Square, its late-night options are somewhat limited. And a trip to the Owl after hours (where you’ll bask in the glory of its life-giving fountain) is like discovering the entire neighborhood in one place. So yeah, there’s gonna be a lot of flannel.
Everyone loves the Hideout. And seriously, what’s not to love? Understated, fun, and full of life, this place is about as Chicago as they come. Check out live bands, party in the parking lot during the Hideout Block Party, or just chill in the front room making friends with strangers. It’s all good.
aliveOne is a rite of passage for any self-respecting Chicagoan. The city’s finest live music jukebox, alarmingly fun live shows in the back room, and an always-a-good-time, up-for-anything young crowd of 20-somethings make it the kind of place that old dudes in their 30s can’t resist either.
If the mussels and frites is a dish to eat before you die, then surely the bar itself (which just so happens to be one of America’s finest beer bars) is somewhere to drink before you die, right? That’s just logic.
So you’ve danced at late-night bars. Ever dance in a late-night chain link fenced-in dancing cage? If not, you’ve obviously never been to Exit. Stop by on the third Thursday of the month for one of Chicago’s craziest parties. Yes, it involves blacklights and body paint.
26. Alice’s Lounge
Karaoke 'til 4am. We repeat: karaoke 'til 4am. What more do you need to know?
While not quite as heralded as its big brother Hopleaf, Simon’s keeps the vibe fun and low-key with a neon sign of a fish drinking a martini, Schlitz cans, and plenty of Viking paraphernalia. Plus Al Capone was rumored to supply this Swedish stalwart with bootlegger whiskey during Prohibition, so that’s something.
28. Map Room
Love to show off your knowledge of the location of Kyrgyzstan while drinking with your buddies? Love thumbing through old copies of National Geographic to spot nudie pics? Come to think of it, both of these activities would make decent drinking games.
Why would arguably the worst bar in Chicago be on a bucket list? If you start here, there’s nowhere to go but up.
30. Crabby Kim’s
Crabby Kim’s is a bikini bar -- which means bachelor party or no bachelor party, this is one of those things you need to do at least once in your life. Because twice would be creepy.
What can be said about Maria’s that hasn’t already been said? A top beer bar in the nation, where the Marz drafts runneth over, combined with the liquor store selections worth picking up on the way out, make it a Bridgeport institution.
Making our list of bad decision bars in Chicago is an accomplishment in itself. But you know you’re really occupying rarefied air when you are one of the worst decision bars in AMERICA. Which is a pretty big place.
33. Twisted Spoke
It's got whiskey. It's got Bloody Marys. It's got nachos, fried jalapeño poppers, and hell, it's even got rooftop brunch. But what does this biker bar have that other bars don’t? Smut and eggs. Which is exactly what it sounds like.
34. Fischman Liquors
Everyone loves a good slashie. But if you can get yours with the occasional food truck and live band in the parking lot, why the hell wouldn’t you?
With punk music blaring and walls as black as night, Delilah’s is the quintessential shot-and-a-beer type of place. And with shots coming in more than 600 varieties, you could be here a while.
36. Local Option
The mainstay beer bar with 30+ taps and 100+ bottles is your go-to source for Morning Wood -- the oak-aged coffee amber ale, not the, well, other kind. Complete your own beer pairings with a Creole-inspired pub menu that features some tasty tots.
Drinking? Fun. Drinking in a Tiki bar? More fun. Drinking in a secretive Tiki bar pouring one of the strongest drinks in the city? Bucket list-worthy fun.
As Chicago’s most jaw-dropping location for drinks and one of the city’s finest rooftop bars (also open year-round), inclusion of the Signature Room on the 95th floor of the Hancock Building should surprise exactly no one. Just be sure to bring plenty of pocket change.
39. Twin Anchors
One of Chicago’s oldest bars is famous as a former Sinatra hangout. And if it was good enough for Old Blue Eyes, it’s certainly good enough for you and your idiot friends.
40. Punch House
If you’re a fan of consuming strange punch concoctions in basements (and, honestly, who among us isn’t?), you’re a fan of Punch House. If the tequila- and wine-packed Space Juice isn’t enough to get you all hot and bothered, the bar’s proximity to upstairs restaurant Dusek’s and adjacent music club Thalia Hall is. It’s not a bad date idea, either.
For all the hoopla surrounding the West Loop’s food and drink scene, there are surprisingly few bars that are bucket list-worthy. While Lone Wolf and Kaiser Tiger are fine establishments in their own right, Maude’s stands out from the pack thanks to its sleek European feel, killer cocktails, and sexy vibe fit for any occasion. Like crossing bars off of bucket lists.
If you like your bar food meat-free, this is the place for you. Cap off your 606 stroll with a pair of catfish tacos, you’ve earned it.
If a band like Neon Indian is WAAAAY too mainstream for you, check the obscure band section off your bucket list at the tucked-away venue inside the Burlington.
45. Big Joe’s
Two words: turtle racing.
46. Smart Bar
A dance club for people who don’t like dance clubs, Smartbar consistently hosts the finest DJs in the city with a dance floor that is practically calling out for you to spill beer on it while attempting to “dance.” Its chill vibes and lack of pretension make it bucket list-worthy in its own right, but when bands DJ here after playing a show at Metro upstairs you’re really getting your money’s worth.
47. Schaller’s Pump
It’s Chicago’s oldest bar. It was built in 1881. It’s where Mayor Daley celebrated his 21st birthday. If that’s not Chicago bucket list-worthy, we don’t know what is.
48. Rose’s Lounge
If you’ve ever partied in your grandparents’ basement, it surely bore a striking resemblance to this funky hodgepodge of dusty old furniture, Christmas lights, gumball machines, and $2 Old Style drafts. Well, your grandma lives in Lincoln Park. Her name is Rose. And she lives upstairs. Go say hi.
49. Liar’s Club
Your choice of bar can say a lot about you. And at Liar’s Club, it says one thing and one thing only: you came to party.
50. Carol’s Pub
You haven’t experienced Chicago late night until you’re experienced the joys of a Chicago country bar late night. And unlike most late-night bars stuffed with meatheads and girls crying into their cellphones, Carol’s is a joyous place full of friendly people, good vibes, and yes, country music.