CHIGuide
The Best Bars in Logan Square
photo credit: Jude Goergen
There are few neighborhoods more bar-crawl-friendly than Logan Square. Pick a street, any street—the endless restaurants of Armitage, overflowing dives of Milwaukee, or exciting new options along Diversey—and go door-to-door sipping cocktails and downing cheap beers until you succumb to the siren song of The Freeze. When it comes to nightlife, there’s no shortage of options here, from classic cocktail lounges to tropical bars, but these are our 21 favorites. And don’t forget to hydrate—when it comes to a night out in Logan Square, it’s a marathon, not a sprint.
THE SPOTS
photo credit: Kim Kovacik
Best Intentions is the dive bar to rule all dive bars. Cheap beer. Affordable cocktails (around $10) that don’t taste like rocket fuel diluted with tonic water. Throw in $6 cheeseburgers, some free arcade games, and a cute secluded back patio, and it’s easy to see why everyone seems to love this place. And we mean everyone. Since they reopened after being closed for three years, every bar stool is always taken.
Aside from a few bleacher-style seats on the side, there aren’t too many places to sit at Slippery Slope. Which is fine because you’re not here to peacefully sip on a beer under their red lights like a resting lizard. You’re here to dance your ass off. Just get there early—the booming DJ sets and dance floor are so popular there’s often a long line outside. But if you need a break, feel free to try and beat the high score on their skeeball machine, or grab an excellent cocktail from their more low-key second-floor lounge, The Heavy Feather.
photo credit: Jude Goergen
Just above Slippery Slope is its retro-themed lounge, The Heavy Feather. Unlike its sibling, The Heavy Feather is more relaxed, with plenty of standing tables, leather booths, and comfy 70’s-esque leather rolly chairs you can turn into the teacup rides at Disneyland. The focus here is on cocktails, and they’re all excellent—from well-balanced espresso martinis and mezcal Old Fashioneds, to a grasshopper that’s everything you want in a boozy milkshake. They don’t have food, but if you’re lucky, a guy selling tamales might make a midnight appearance (though it’s not the Tamale Guy).
photo credit: Clayton Hauck
Union comes from the same team behind Lardon, and just like its sister spot next door, the food at this barstaurant is great. The dishes on the menu aren’t your typical bar snacks: lightly breaded fried olives filled with mortadella, or lamb and pistachio meatballs. They also have an amazing burger: it’s got a thick brisket and chuck patty topped with crispy onions and bone marrow aioli And just in case you lost yourself in the burger and forgot this place was a bar, they have plenty of different whiskeys and creative Old Fashioneds.
photo credit: Clayton Hauck
This cocktail lounge is a third spot from the Union and Lardon team. And though not technically a speakeasy, its secret clubhouse aesthetic and discreet, side street entrance channels hidden bar energy. Inside, you’ll find a dark wooden space, comfy leather couches, and tasty small plates and drinks. We like snacking on their smoky grilled jerk chicken hearts or turkey empanadas, especially while sipping on something from their rotating, themed drink menu. Currently, it’s full of cocktails named after birds, like the boozy-yet-refreshing Cedar Waxwing with gin, sotol, amaro, and green chartreuse plus some lime and mint.
Grabbing a seat at Quality Time in Logan Square feels like being an extra on the set for That 70’s Show, thanks to the rustic wooden interior and vintage leather seating. The front area is fairly small, but they also have a back room with more booths and a spot for weekend DJ sets. But even at its busiest, it never feels like a club—it’s still great for a low-key hang. Their solid drink menu includes originals like the Alone In Paradise, a fruity-yet-boozy rum and mezcal drink with passionfruit and pineapple. Plus, they also have tamales from the Tamale Guy, and we can’t think of a more ideal 12am snack.
photo credit: Jeff Marini
This bar is like a magician’s hat—despite its appearance, it somehow has enough room for plenty of people to dance during their live DJ sets. The cocktail menu has a wide range of options, from fruit-forward drinks with lychee and grapefruit, to stronger ones with mezcal and absinthe. But if “sitting” ranks higher than “dancing” on your favorite activities list, just check their event calendar ahead of time for more relaxed jazz or solo guitar performances.
photo credit: Sandy Noto
No bar crawl along Milwaukee is complete without a stop at Cole’s. In terms of drinks and atmosphere it’s what you’d usually expect from a dive: solid draft list, cheap cocktails, a pool table, and a slight mustiness from a place that feels like it’s existed before the dawn of time (despite only being around since 2009.) But the real reason to come here is for the live music and events. There’s a weekly comedy open mic in the back, and bands often come through and perform free shows. If you care about being able to brag about seeing a band or comic before they made it big, there’s a good chance this will happen at Cole’s.
photo credit: Clayton Hauck
This two-story spot is part retail shop and part wine bar. The first floor is like a tiny library, with shelves stocked top to bottom with bottles of everything from the Tolstoys to the John Grishams of wine. The second floor is where you’ll find the much more spacious bar—full of high tables, wooden booths, and occasionally, live music or a restaurant pop-up. They also happen to have great happy hour deals where a glass or a cocktail only costs $8.
Sometimes you just want to be a kid again, but with a beer in your hand. Consider Emporium, a Chuck E. Cheese for grown-ups. Retro arcade games fill the bar, along with foosball tables, a vintage truck, and vibrant murals. The sprawling space is one of the more popular spots in the neighborhood, thanks to its large canned beer list and the occasional appearance of a DJ in the back near the air hockey tables. If you’re looking for somewhere to bring a bunch of friends, grab a round of shots, and challenge everyone to prove their dominance on NBA Jam, this is it.
Billy Sunday is a higher-brow cocktail bar where some drinks have names like the Victorian and others are made with vintage liquors and cost around $30. It’s the kind of place you take a first date to impress them with your knowledge of rare amaro (take a gander at the bottles with the faded labels on the back bar). The intimate space only seats 50, which makes it ideal for quiet conversations under the crystal chandeliers, but not the best for a group hang. Snag a seat at the bar, if you can, for the best view of all those old bottles, as well as the bartenders mixing up things like the house Old Fashioned and Amaro Daiquiri.
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photo credit: Christina Slaton
Estereo is one of those bars that draws you in—partially because of the garage door-style windows that give anyone on the sidewalk a peek at the action inside. Once you give in to the call of tequila, you’ll be rewarded with a one-way ticket to some of our favorite cocktails in the neighborhood. Drinks here are named after their main spirit—mezcal, pisco, cachaça —and feature seasonal juices and tinctures. A refreshing frozen tequila drink with aperol, guava, and lime will make you forget that another oppressive Chicago winter is right around the corner. Did we mention it opens at noon? Yeah, good luck ever leaving this place.
What’s not to love about Hopewell? It was co-founded by a woman? Love that. They make great merch, love that too. Its taproom is designed to be welcoming to all sorts of beer drinkers, and not just pretentious experts? Very much love that. The space is bright and airy, with plenty of space for groups, and they also have a cute retail section. Which means you can grab a Ride or Die pale ale at the bar and then pick up a bottle of Neon, its mixed-culture sour ale, and a Nopewell t-shirt for the road.
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We like to think of The Native as the Cheers bar of Logan Square. It’s a place where everyone knows your name and, if they don’t, they’ll shower you in boozy slushies until names don’t really matter. While it only opened in 2017, this cash-only spot feels like it’s been here forever—complete with leather booths and a long wooden bar perfect for downing pints of High Life. There’s also a seasonal back patio, which occasionally hosts pop-up events. It’s a great place to get to know one of the bartenders over a few shots of Malort, as they really are some of the friendliest around.
One look at Outside Voices’ menu proves that, while this bar might have one of the most interesting wine lists in the neighborhood, they don’t take that acclaim too seriously. It’s a choose-your-own-adventure wine bar of sorts, where inside you’ll find a slice of California, with exposed brick, light wood architecture, and viney plants. Outside, it feels more like our coolest friend’s backyard, with picnic tables, fire pits, and plenty of Astroturf. Even the charcuterie boards here have a playful side, with a selection of meats and cheeses served with a sleeve of Ritz crackers.
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Let’s start with the real reason we go to Scofflaw: midnight cookies. That’s homemade chocolate chip cookies for free every night since the gin-focused bar opened in 2012. These days, those cookies make an appearance at 11pm, and you can bide your time until then by sipping on a tropical Neptune or a boozy Dusk Buster, either next to the fireplace surrounded by vintage furniture or at the marble bar. But because we can’t live on cookies alone, as tempting as that sounds, order their fantastic cheeseburger.
Chicago beer drinkers have been seeking out the made-in-Naperville IPAs and pale ales from Solemn Oath since 2013. After many delays (the project has been in the works since 2019), the brewery’s first Chicago taproom opened in 2021 on a busy strip of Armitage. And man, was it worth the wait. We’re talking about a classic Chicago tavern, complete with a Brunswick-style bar topped with a hand-painted mural. Of course, all of the Snaggletooth Bandana beers and Lü you’ve come to know and love are here on draft, along with coolers filled with beer to go. Plus, with everything from food pop-ups to pool tournaments, there’s always something cool going on here.
As far as beautifully restored old bars go, Spilt Milk is one of the finest specimens we’ve ever seen. The bar retains much of its throwback charm with vintage refrigerators, gold-painted tile ceilings, and the ornately carved wood bar. There’s no way to go wrong here, but we like the smoky Logan squares with bourbon, banana-infused syrup, and tobacco bitters, or try one of the rotating frozen drinks if you’re in the mood for a boozy slushie. Swing through on Mondays in the summer and get treated to Family Meal Monday on the back patio, where guest chefs from nearby restaurants serve a special menu of backyard-friendly dishes for $20 per plate.
Way Out is a dark and brooding bar - meet a first date here and you might leave not knowing exactly what they look like. Good thing you don’t need to see the pizza potstickers and taquitos to know that’s exactly what you want to eat after a few drinks. Maybe that drink is the Bitter Baby, which is basically a boozy pink lemonade, or a $5 mojito shot. With large turquoise booths and plenty of bar stools, as well as extraterrestrial art, it’s a fun place to hang out for a little longer than you planned. And just when you’re ready to leave, you’ll remember there’s a pool table and jukebox in the back. It’s going to be a long night.
With new bars popping up all along Milwaukee Avenue, it’s easy to overlook some of the places that helped make Logan Square the drinking destination that it is today. Opened in 1994 in Lincoln Park and relocating to Logan Square in 2014, Webster’s Wine Bar has anchored the Square with oysters and wines by the glass for nearly a decade. These days, its wine list centers on natural stuff, with bottles ranging from the Loire Valley to Basque Country. Grab a glass of something funky and orange and pair it with a round of Island Creek oysters or a cheese board at the large bar or one of the distressed wood tables overlooking shelves filled with books and bottles. It’s a cozy and sophisticated escape that, with any luck, will be around for years to come.
photo credit: Welcome Back Lounge
DJs, a bus turned into a bar, plates of loaded tater tots served at picnic tables on the Astroturf back lawn - Welcome Back Lounge has it all. Inside, people crowd the retro bar - with a blue checked floor and sleek wood bar straight out of the 70s, plus a light-up bingo board, which is put to good use on Monday nights - for cans of Maplewood Pulaski Pils served in bright yellow koozies. Outside, they pack picnic tables to enjoy patty melts and a Campfire Lemonade with mezcal and Four Roses. Whether you’re “enjoying” some Jello shots or snacking on mini corn dogs, it’s safe to say you’re doing so at one of the more unique (and raucous) bars in the neighborhood.
