New bars open all the time in Chicago - some gangster-themed tiki bar or Australian beer garden probably just opened around the corner from wherever you're currently located. But there's no better place to drink than a classic.
So we compiled a list of our favorites - the places we find ourselves returning to over and again. Some are older than others, but they're the standbys that we can rely on for a number of different occasions. They are the places that make this city great. In other words: the Greatest Hits.
If you live in Chicago, you should drink at them all. If you’re visiting, check out as many as you can. Some spots are cocktail bars, some are dives, others have live music, and then there are a few that fall somewhere in-between. All of them are essential Chicago watering holes.
Looking for a restaurant version of the Greatest Hits List? We have that too.
The city of Chicago outlawed smoking in public spaces including bars and restaurants, back in 2008. And Richard's Bar gives absolutely zero f*cks - you will smell like you shot a 1966 Marlboro commercial when you walk out of there. Combine that with the classic Old Style sign out front, neon lights inside, cheap beers, and a jukebox filled with plenty of classics, and you'll immediately see why this is one of the great dive bars in town.
Character is not something Old Town Ale House is short on. At its core, Old Town Ale House is a funky dive bar and historical hangout full of locals and comedians because of its location near Second City. The longtime owner also treats it as his own art studio, which includes pictures of Vladimir Putin as a ballerina and Kim Jong Un and Dennis Rodman together on the wall. It's the total opposite of everything else you'll find near it on Wells St., which makes Old Town Ale House the perfect escape for a low-key couple of drinks.
From the outside, the brick wall, plain green sign, and metal bars on the tiny window out front don't make Skylark look like an appealing place. And inside is equally as uneventful as far as decorations go, mainly because there aren't any. But that's all part of the charm at this Pilsen dive bar, and simplicity is what makes it so great. It's always lively, the drinks are around $5, and bar food like burgers and tater tots are always great. Just make sure to bring cash because it's all they accept.
Wicker Park has seen a lot of changes since the 1930's, but there haven't been any changes to the Rainbo Club. Ownership has been the same for a long time, drink prices are always low, and Rainbo Club maintains its gritty roots despite the fact you're more likely to see babies in strollers in the neighborhood than you are any actual crime. And you have to respect their unwillingness to change.
The stretch of Division Street between Ashland and Damen is lined with enough bars to please any type of situation or personality. But head a couple blocks south of the craziness on Wolcott where you'll find Happy Village, a much more low-key but truly great spot. The long-standing neighborhood bar is on a quiet street where the drinks are always cheap. The front room has a very dive-bar feel, there's a ping pong room on the side that often has some seriously competitive action, or check out the excellent beer garden out back with patio furniture that looks like it was thrown together from a garage sale.
Green Door Tavern has just the right amount of old man cranky tavern on the corner vibes, while still managing to be cool. The building was built approximately a million years ago in 1872, and it's been a bar and restaurant for almost 100 years. Not only did it survive prohibition, but the basement functioned as a secret bar during those times. Today, the secret basement bar is a separate area known as The Drifter where you can get creative cocktails and catch a burlesque show. But we rely on the main floor of Green Door, where it's always a laid-back good time.
Like oysters or puppies, great things come in small packages. And the same can be said for The Matchbox, one of the tiniest bars in town. What The Matchbox doesn't have in space it makes up for in personality. You'll literally struggle to get past other people sitting at the bar to get an open seat, but the friendly atmosphere will make you feel right at home. This is the kind of place where bartenders know the regulars, but they'll be equally as friendly to any newcomers who walk in the door. Come with one other person to kick it over classic cocktails and conversation.
Walking into Danny's feels more like stumbling into a cool house party complete with a DJ than it does an actual bar. That's because the building literally looks like a house and sits on an otherwise quiet, residential Bucktown street. The type of music played on any given night definitely dictates the mood, but there's enough room to dance or escape to the upstairs room if you prefer. House parties were always more fun anyway.
Maria's may not have always been formally called Maria's, but everyone who frequents the Bridgeport bar knows that Maria Marszewski has long been the driving force behind this slashie (liquor store and bar combo). When her kids took over in 2010, they gave the place a facelift and made "Maria's" the official name. But it's still the same friendly neighborhood place to post up for a quality selection of beers. You can even get food now from the attached Kimski, which means there's really no reason to ever leave.
Delilah's is one of the more eclectic bars in the city, and it shows in everything they do. Extensive whiskey list over 500 kinds deep? Check. More than 200 different beers? Yup. Do the walls feature a rotation of different local artists? Of course. Does the whole place have a sort of rock and roll feel? Yes, but there are also DJs on hand playing punk rock, metal, reggae, R&B, or even country music any given day of the week. And if that's not already a weird mashup, it's also a go-to spot for Buffalo Bills games during football season, and they're circling the wagons like you'd expect any good Bills fans to do. The whole dynamic gives Delilah's a lot of character, which is especially meaningful for a bar in Lincoln Park.
Sportman's Club is what happens when old-school dive bar meets new-age bartenders who know how to do cool things. The small and skinny space in Ukranian Village had been a local spot for a long-time, but new ownership revamped the place just enough while preserving the old school atmosphere. You can grab an Old Style for $3 or try one of the more interesting cocktails that rotate daily for about $10. Either way, it's a great low-key spot to sit and hang, and if it's nice outside, you'll definitely want to hit their backyard that feels like hanging at someone's house.
There was about a two year stretch we managed to end up at Butch’s on Division Street at least once a weekend. Why? Maybe because it's decorated like Christmas year-round, maybe because we could always count on running into someone we knew, or maybe because Butch's is open until 4am or later every night of the week. But it's probably a combination of all of those things, which is what makes Butch's a quintessential Chicago Irish bar. It's the kind of place you can pop in for a beer literally any time, especially at hours not so socially acceptable to drink.
Dance Party/Live music
If you've never found yourself screaming Woahhhhhhh, we're half way there. WOAHHHHHH, livin' on a prayer at the top of your lungs in the downstairs of the Hangge-Uppe at 4am, then have you even lived? Answer: maybe you're alive and reading this, but try living a little more. The Hangge-Uppe is the perfect mix of wedding, bar mitzvah, and camp sing along all rolled up into one drunken mess, and the DJ knows how to get the people going. You want to end your night here, not start it, which is evident by the fact a line starts to form the later it gets. Even if you think you're too drunk to go to the Hangge-Uppe, chances are you'll walk in and realize you're still pretty sober compared to everyone else there.
Charlie Chaplin, Frank Sinatra, and Al Capone are just a few of the big names who have hung out at this classic jazz club over the 100 years it's been open. Translation - The Green Mill has seem some sh*t. Originally modeled after the Moulin Rouge in Paris, it's still one of the best places to catch live jazz music every day of the week. Rumor has it there's a crazy set of underground tunnels beneath the place where your wildest gangster dreams took place, which is fun to think about even if they won't give you a tour.
Blues Brothers the movie took place in Chicago for a reason, and it's because the Blues culture of this city is alive and well. Just head to a place like Kingston Mines, where you can catch a live show for $12 every night starting in the evening until they close at 4am (5am on Saturday). The longtime bar has been in a few different spots over the years, but it's current Lincoln Park location has been the same for over 30 years.
Revolution Brewing is truly a local beer company, and their Logan Square brewpub is one of the best places around to hang over drinks. Not only does Revolution make an excellent array of beers ranging from the Anti-Hero IPA (our favorite) to the Eugene Porter to the Bottom Up Wit white ale, but quality bar food and a hip warehouse space make it an enjoyable place to sit.
Hopleaf embodies everything that's good about the term gastropub - it's a bar with an exceptional beer selection and a food menu that goes above and beyond typical bar food. Post up in the front room if you're more worried about only the drinks, or make your way to the back if you're looking to have more of a meal. The ever-changing draft beer menu will live you thoroughly impressed . . . and drunk.
The Map Room is part morning coffee hangout and part neighborhood tavern with one hell of an extensive beer menu. It opens every morning to serve coffee, pastries, and some basic food, but the real fun is at night. The Map Room is decorated like a National Geographic exhibit, highlighting a global theme with different country flags and other things from around the world. And the global theme spreads to the beer list too, which has you covered on just about anything. There's no food at night, but you're more than welcome to carry-in or even order delivery to the bar.
Sometimes you're looking to sit down over quality cocktails, a little bit of food, and some warm chocolate chip cookies at midnight. And that's exactly what you can do at Scofflaw. As if Scofflaw wasn't already a great Logan Square cocktail bar to hang out for a date or with a couple friends, they also serve free, freshly baked chocolate chip cookies at midnight. Life would be a lot cooler if everybody did that.
Tiki bars used to be the kinds of places we laughed off, like Jimmy Buffet’s Margaritaville, Señor Frogs, or a bad fraternity party from college full of sugary drinks that cause headaches for days. But tiki bars are cool again, and Lost Lake is a great one. Everything from the banana daiquiri with bananas shaped as dolphins to the $50 "Beachcomber's Rule No. 2: Never Bet On Another Man's Game" you can share with your friends makes for a fun time. It's not a very big place, so you'll often have to wait for a seat. But if you're looking to commit to sitting at one place, Lost Lake is always a strong move.
No cell phones. No baseball hats. No Budweiser. No Grey Goose. These are just a few of the rules at Violet Hour. Normally, we’d say any place that wants to dictate our drinking behavior can go ahead and f*ck right off. But most places aren’t Violet Hour. Hiding behind a mural with a secret door, this is a place with a "head intoxicologist," not a bartender. You'll be given a table with as many chairs as you have people, the seasonal drinks have names like "tears in rain" or "wishful thinking," and you'll sit in a proper setting enjoying some of the best seasonal cocktails you've ever had. It's not an every day situation, but it's a great time for the right occasion.
The Aviary is a science experiment in cocktail form. But that should be expected from the Alinea Group, which applies similar kinds of technique and craziness of their restaurants to the drinks here. Your cocktail might come in gas form, ice form, lit on fire, or maybe poured vertically from the ground up because who knows what they're capable of here. You can sit in the main dining area and order drinks a la carte, but we would suggest trying the three-course cocktail progression for $65 per person. If you want to go all out, do the seven-course cocktail and food menu for $135 - it's expensive, but worth it.
Cindy's is one of the newer bars in Chicago, but we're already comfortable calling it a greatest hit for one particular reason - the views. It sits on top of the Chicago Athletic Association hotel on Michigan Avenue, overlooking Millennium Park and the lake. It's the perfect spot to take out of town friends or just remind yourself how good-looking the city can be.
Lincoln Park has an endless number of bars with dirty keg taps, sticky floors, and flags of Big 10 teams on the walls. But it's lacking in higher-end places where you can grab a cocktail in a nicer setting, and that's where The J. Parker at The Lincoln Hotel comes in. It's not the kind of overpriced and tacky hotel bar where sleazy salesmen from a conference are hanging out. Instead, it's a rooftop bar with excellent views overlooking the park and water - just don't blame us if you can't find a table on a really nice day.
Wrigleyville gets it's own category because there's really nothing like it. And while there are many bars in the neighborhood that we like, especially during baseball season, Murphy's Bleachers is the only one we try and hit up before and after every game. Its location just outside of the right field bleachers entrance has made it the preferred spot for Cubs fans for years, to the point it's un-American if you don't go to Murphy's Bleachers before a Cubs game at least once in your life.