New bars open all the time in Chicago - some Al Capone-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, but all of them are essential to Chicago.
Looking for a restaurant version of the Greatest Hits List? We have that too.
A bar serving cheap beer in a 100-something-year-old house stranded in an industrial corridor. If that sounds like the type of old man bar whose foundation is pure Chicago sweat and grit, that’s because it is - but it’s so much more than that. An inclusive space for some of the best local and visiting bands, podcasts, and comedy shows. A place that passes out blankets at the bluegrass concerts hosted on their porch. The site of one of the best dance parties in the city every Saturday at midnight. The Hideout feels like a cross section of the soul of Chicago, which makes it a great place to get drunk.
The best bar in Wrigleyville really only has one thing in common with the rest of the neighborhood, and that’s the ivy climbing its walls. There’s a large selection of craft beer, and while board games are fairly common at bars in the city, Guthrie’s is probably the only place where every table is halfway through settling Catan or starting in on a do-or-die round of Bananagrams. Add in a screened back porch and a BYOF policy, and this is the perfect place for a group hang or first date.
Whether you’re just grabbing a beer after a show at Cafe Mustache or you’ve got your all-night dancing shoes on, a night out on this strip of Milwaukee will probably include a stop at Cole’s. It’s unpretentious and occasionally sweaty, serves reasonably priced drinks, and attracts people from across the city. There’s a weekly comedy open mic in the back, and bands often come through for free shows. If you’re looking to see a band or comic who will eventually blow up and leave Chicago behind for some unthinkable reason, there’s a good chance you can do it at Cole’s.
Big Chicks is as much a neighborhood staple as it is a welcome alternative to some of the more sceney LGBTQ spots in the city. There’s a camaraderie here that even extends to the menu - free Sunday BBQs in the summer and $1 burgers on Mondays make it a destination on nights when other bars are deserted. Plus, the fact that it’s owned by the same folks as Tweet next door means the bar food is much better than most of the other places serving you well drinks in plastic cups.
Best Intentions is where you should come to drink your sorrows away, meet your Hinge date, and throw your birthday party. That’s because it’s a divey corner tavern, fancy cocktail spot, and outdoor cabana bar all in one. There are plenty of cheap bottled beers here, and outstanding takes on classic cocktails sit next to drinks like horchata margaritas (which are also great). The food menu ranges from pickled eggs and french fries to harissa chicken and calf liver paté, but your best bet is the $5 cheeseburger that looks and tastes like a dressed-up Quarter Pounder.
A longtime Hyde Park bar that feels like it’s somehow simultaneously occupying the ’70s, ’80s, and ’90s. You might forget it’s the 21st century at all in here - or you would, if not for the large, impressive mural of President Obama on the wall. There’s sort of a nautical theme at The Cove, in the same way a middle school dance might celebrate “A Night Under The Sea.” For the most part, it’s just a classic dive with a cool layout that’s filled with dedicated drinkers of all ages.
Estereo is our favorite place to day drink in the city. The open garage door walls, the panting dogs, the throwback Latin vinyl on the record player - everything combines to create the perfect setting for drinking refreshing cocktails made with spirits like pisco, singani, and cachaça. At night it’s even more of a party, with a line out the door and live DJ sets on the weekends.
One of the standouts in a neighborhood full of great LGBTQ bars, Sidetrack is a party all week long with show tune sing-alongs, drag shows, and giant TV screens that play music videos according to the night’s theme. It’s usually packed here, but even on its clubbiest nights there’s no cover, which is a rare gift. If you’re not feeling the energy in a certain room, take one of the deceptively strong frozen cocktails for a walk upstairs and a change of scenery.
Whirlaway is one of the best examples of a true Chicago neighborhood bar. The owner, Maria, is usually bartending and is an integral part of the experience here. Once you’ve been here a few times, you become a familiar face and are then treated as such. If there’s a Cubs game on, she’ll probably talk to you about baseball, and when you say the Marlins are your favorite team she’ll grab the attention of the regular at the end of the bar who’s from Miami, and just like that, you’ve got a new drinking buddy - and an understanding of what makes this place special.
The city of Chicago outlawed smoking in 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 here. 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.
There are plenty of places to dance in Chicago, and this corner of Logan Square houses a lot of them. Slippery Slope is a great dance bar, but what separates it from the pack is Heavy Feather, the upstairs bar that’s styled to look like a ’70s-era fern bar. The wood trim and gold accents are a great counter to the red glow of the first floor, and it’s perfect for slowing things down if you’re tired of dancing. This is also a great low-key date spot during the week, with a cocktail menu full of updates on disco-era drinks.
Wicker Park has seen a lot of changes since the 1930s, but there haven’t been many changes to the Rainbo Club. Ownership has been the same for a long time, drink prices are always low, and the place maintains its gritty roots - behind the bar is a defunct but sort-of-elegant burlesque stage that encapsulates the grungy history they’ve kept alive all these years. You have to respect their unwillingness to change.
From the street, 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.
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. 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.
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, and 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.
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. The mussels and Belgian-style frites rightfully get the most attention here, but the entire menu is worth your time. Hang out in the front rooms to spend time with their draft list, the upstairs bar to explore their extensive list of bottles and cans, or make your way to the back room and patio if you’re looking to have a sit-down meal.
Once upon a time, tiki bars were the kinds of places we completely disregarded because of terrible knock-offs like Jimmy Buffet’s Margaritaville. But tiki bars that actually care about the drinks they’re serving you are an entirely different story. Lost Lake is a prime example - a place where your bartender will not only know much more about rum than you, she’ll concoct a large-format drink that’ll take you and your friends on a trip to an island far, far away from the cold winters of Chicago.
The Blues Brothers 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 every night starting in the evening until they close at 3:30am (4:30am 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.
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.
Even though the hype behind The Violet Hour (and the backlash over its strict rules about what you can wear and what drinks you can order) isn’t as strong as it once was, the drinks here are still really damn good. Good enough that you should still seek out the entrance hidden behind an ever-changing mural in Wicker Park. From the way they seat you like you’re at a restaurant to the upscale bar snacks - expect foie gras and tartare - the experience here is all about curation, and they’ve created the right setting to enjoy some of the best seasonal cocktails you’ve ever had. It’s not an everyday situation, but it’s a great spot for the right occasion.
Old Town Ale House
Character is not something Old Town Ale House is short on. At its core, Old Town Ale House is a funky dive bar and historic 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.