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 15 favorites. And don’t forget to hydrate - when it comes to a night out in Logan Square, it’s a marathon, not a sprint.
Located under the Blue Line tracks is a patio so perfect, you’ll wonder why you drink outside anywhere else. This former parking lot has been transformed with picnic tables, potted plants, and strings of twinkle lights, making it one of the best spots in Logan Square to pull up with some friends for a glass or bottle of wine. The focus here is natural wines, but you’ll also find plenty of local beer and cider. However, it’s more than just a great patio for drinking, it’s also a bottle shop and an indoor wine bar featuring DJs on the weekends. Check the bar’s Instagram for its pop-up schedule too, showcasing birra tacos-makers, hot dog carts, and burger nights.
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 drinks have names like the Victorian and Act II, Scene II. It’s the kind of place you take a first date to impress them with your vintage amaro knowledge (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.
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. Right now, we’re all about the bright pink tequila cocktail: the bubbly blend of sotol, prickly pear, and lime will make you forget that another oppressive Chicago winter is right around the corner. The bar is dog friendly and recently began offering pizza delivery from nearby Pizza Lobo. Did we mention it opens at noon? Yeah, good luck ever leaving this place.
Hopewell Brewing Company
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 bright and airy brewery on Milwaukee Avenue morphed into the Hopewell Supermarket during the pandemic, but has since reopened its taproom while also keeping the store alive and well. That 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. Stop by on Fridays at 4:30pm to partake in pre-shift Fridays, where the bar pours samples of the brewery’s latest releases.
It’s been a long pandemic without the tropical escape that is Lost Lake. In 2020, the lounge closed its bar and opened a takeout window, and has been serving Tic-Tac-Taxis and Oaxacan Old Fashioneds in cute branded bottles ever since. This place reopened for bar service at the end of August, with a new food and reconcepted drink menu too, featuring things like double-fried catfish and Kelp Daiquiris.
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. Opt for a Black Muscat Rosé with notes of Fruit Loops or an Argentinean Torrontés that kind of screams “fruit-on-the-bottom peach yogurt.” Even the charcuterie boards here have a playful side, with a selection of meats and cheeses served with a sleeve of Ritz crackers.
Chicago’s beer scene will never be the same thanks to the addition of Pilot Project, Chicago’s first brewery incubator. What’s a brewery incubator, you ask? In addition to their assortment of house-brewed beers, the space hosts a rotating assortment of beverage startups - Dutchbag Brew Co., Luna Bay Hard Kombucha, and Azadi Brewing all got their starts here. In addition to being innovative, the brewery is also beautiful, with a lounge area filled with overstuffed couches and plenty of communal tables, as well as a sunny patio flanked by murals. Sip a Spanish tea-infused IPA in the industrial taproom, or at one of the outdoor picnic tables, and pair it with a giant soft pretzel or a tray of brewer’s nachos.
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 a charcuterie board to balance out all that gin. Also, if you’re looking for the bar’s famous burger, it’s currently on hold as they search for a new chef.
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 this summer 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 Lu you’ve come to know and love are here on draft, along with coolers filled with beer to-go. Keep an eye out for the final touch of this new taproom: a pool table that will set up shop next to the communal tables.
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 Sarsaparilla Zazerac, a take on the classic made with almond sarsaparilla syrup that’s been on the menu since the bar opened in 2016, or try one of the rotating seasonal drinks, like the refreshing Cucumber Oasis. Swing through on a Monday 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 taco fingers 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 Cosmo 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.
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 Back Yard Punch. 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.