Chicago has always been a hard-drinking town and it still is despite the growing prevalence of tequila bars, whiskey bars, and self-styled “speakeasies.” All those places have their charm, but there’s often a see-and-be-seen element to them as well. Sometimes you just want a few drinks with minimum fuss, and the following Chicago spots offer a straightforward, elbows-on-the-bar experience.
5210 N Clark St.
For 80-plus years, Simon’s has been a fixture in Andersonville, a North Side neighborhood with a strong Swedish heritage. The room where original owner Simon Lundberg started serving whiskey during Prohibition is now a storage area. In the main room, the wall opposite the bar features a mural titled “The Deerhunter’s Ball,” painted long ago by one of Lundberg’s fellow Swedes. Drinks include Nordic potato vodka, a notorious Chicago concoction known as Malort, and of course glögg (aka gløgg or glugg), the Swedish wine that Simon’s brews and serves during cooler months.
It’s impossible to sit at the bar inside Simon’s without feeling an overwhelming sense of history. Also, the love that bartenders and patrons have for the place is evident. Simon’s atmosphere is the exact, wonderful opposite of a scene.
Green Door Tavern
678 N Orleans St
A nightclub vibe permeates much of the River North neighborhood, thanks in part to its proximity to the Magnificent Mile, Chicago’s tourist hub. But there are a number of hidden gems in the area, including the Green Door. Founded in 1921, this unassuming bar started as a grocery store before transitioning to an Italian restaurant, and then becoming a speakeasy.
The original speakeasy is still downstairs, but the main upstairs area has a distinctly homey feel. The drink menu includes specialty cocktails that hark back to the Prohibition era, complemented by a respectable beer offering, and the kitchen serves solid, well-prepared bar grub. Every inch of wall space is covered with old photographs, neon signs, vintage advertisements, and countless pieces of ephemera, which taken together offer a jumbled history of the place itself. Best of all: no velvet ropes, no cover charges, and no nightclub attitude.
1150 N Damen Ave
To be clear: the Rainbo is a scene, but it’s a scene par excellence, one that began in the 1990s when Urge Overkill, Liz Phair, and members of the Smashing Pumpkins held court here. (During the early 2000’s, it was even said that a member of post-rock luminaries Tortoise worked behind the bar.) After the movie “High Fidelity” filmed a scene at the Rainbo, the bar’s street cred compounded, prompting rock critic Jim DeRogatis to describe the place as “the nexus of Chicago’s hipster music scene.”
The bar’s history goes back to the 1930s, and hardscrabble heroes like Nelson Algren reportedly drank here. To the Rainbo’s credit, amid all the music-scene glitz, the bar retained its grit. The place is without question a dive. As the latest generation of indie rockers and art-school kids converge, we recommend that you grab a seat on the far side of the wraparound bar, and just like Mr. Algren would have, take in the scene.
2771 N Lincoln Ave
A man posting an online review of Delilah’s claims that while he drank on the second floor, a rat ran across the room. Strangely enough, the guy considered this a bad thing. In reality the incident illustrates everything that is wonderful about Delilah’s. The bar stocks more than 200 beers and ciders, and is legitimately world-famous for its whiskey selection, which totals 750 options from 15 countries. But the ambience is more spit than polish. The interior is dark and seedy, and while you’re savoring that 20-year-old malt, there’s a good chance a DJ will be blasting punk or vintage R&B. Delilah’s proves that you can have top-shelf substance without putting on airs, or even getting distracted by frivolous city-health codes.
Gold Star Bar
1755 W Division St
Each of the bars we’ve mentioned has a signature physical feature, whether the Rainbo’s photo booth, Simon’s mural, Green Door’s speakeasy, or Delilah’s rats (or that awesome little lounge next to the bar). The Gold Star, on the other hand, has nothing. Yes, there’s the free popcorn, outstanding jukebox, and pool table where neighborhood cult heroes like the Bread Lady (or Muffin Lady, for those in the know) played eight-ball. But nothing tangible about the place really jumps out. When you think back to your times at Gold Star, you’re unlikely to recall the place itself. Instead, you’ll remember the people you were with, and the conversations you had over a few cheap, unremarkable beers. And that just might make Gold Star the best bar on this list.