12 Best Winter Bars in Chicago
You know one of the best things about Chicago’s bar scene? The fact that no matter what type of experience you are looking for, this city has it. So settle in this winter with some our favorite and most unique spots in the city to loosen up and enjoy Dabble's winter guide to Chicago's bars for 2019!
Photo Cred: Dabble
Best Bar to Dabble in a New Craft: West Town
One of the newer members of Chicago’s emerging Brewery District, Midwest Coast Brewing offers great beer in a welcoming and huge taproom that is dog-friendly! Their stouts, APAs, IPAs that we’ve tried are all stand out. Regular Dabble events from dog-treat making to pumpkin carving. Worth a visit!
2137 W. Walnut, http://midwestcoastbrewing.com
Photo Cred: Lone Wolf
Best Bar to Go Old Schoo (or Old Fashion) In: West Loop
Among all the high-end bar and restaurant offerings along Randolph in the West Loop, it could be easy to overlook Lone Wolf with its modest exterior, but inside is what can best be described as high-end dive with craft beers and classic cocktails worthy of the price of their $16 Signature Old Fashioned.
806 W. Randolph, http://www.lonewolftavern.com/
Photo Cred: Sidetrack
Best Bar to Get Musical In Bar: Boystown
This staple nightclub in Chicago’s predominantly gay neighborhood, Sidetrack is known for serving up super boozy slushy drinks and their showtunes-theme nights like Musical Mondays karaoke and Thursdays Pop Rocks dance parties.
3349 N. Halsted, https://www.sidetrackchicago.com/
Photo Cred: Gutheries
Best Bar to Get Board In Bar: Wrigleyville
Guthries Tavern is somewhat of an anomaly - a Wrigleyville bar that doesn’t charge obscene covers and isn’t wall-to-wall with sports bros. What it does offer is the chance to hunker down in a relaxed dive bar setting with dozens of craft beers on tap and more than 60 board games to partake in.
1300 W. Addison, http://www.guthriestavern.com/
Photo Cred: Queen Mary Tavern
Best Bar to Set Sail for Scotch In Bar: Wicker Park
This neighborhood tavern once ran by the “Queen of Division” Mary Kafka, was long-shuttered for more than four decades but was recently reopened, now operating as a cozy maritime-themed cocktail lounge, the Queen Mary is known for their seemingly endless selections of fine Scotches.
2125 W. Division, http://www.queenmarytavern.com/
Photo Cred: Heavy Feather
Best Bar to Hustle Up a Drink In Bar: Logan Square
Located above Slippery Slope, Heavy Feather offers a timewarp to ‘70s culture with this disco-inspired fern bar. Craft cocktails, gold mirrors, and polished walnut make this a great lounge to relax in with friends.
2357 N. Milwaukee, http://www.heavyfeatherchicago.com/
Photo Cred: Cory & Kerry
Best Bar to Have a True Chicago Irish Experience In Bar: Beverly
Chicago’s favorite Irish Pub housed in the southside Beverly neighborhood, Cork & Kerry encourages an approachable atmosphere with vintage photos and authentic Irish décor that creates the perfect spot to hang out for a happy hour pint.
10614 S. Western, https://corkandkerry.com/
Photo Cred: Jerry's
Best Bar to Have a Beer and a Bite Bar: Lincoln Square
A former Wicker Park staple, Jerry’s recently relocated to its new home in Lincoln Square. Fortunately, the menu has not changed with more than 60 amazing sandwiches and an equally impressive craft beer list to pair with.
4739 N. Lincoln, http://jerryssandwiches.com/
Photo Cred: Delilah's
Best Bar to Let Your Punk Flag Fly-In Bar: Lakeview
Rated one of the best bourbon bars in Chicago, Delilah’s embodies the spirit of punk-rock. While you’ll find good whiskey on the menu for cheap prices, Delilah’s frequently has movie nights, DJs spinning punk and ska, and beer and liquor tasting events.
2771 N. Lincoln, http://www.delilahschicago.com/
Photo Cred: Hopleaf
Best Bar to Get Your Beer Nerd Game On Bar: Andersonville
A perpetual northside favorite, Hopleaf serves a large selection of Belgian-style beers and the most authentic mussels and frites you’ll find in the city in a setting that is both perfect for a large gathering with friends or for a romantic night for two.
5148 N. Clark, https://www.hopleafbar.com/
Photo Cred: Game Room
Best Bar to Get Your Game On In Bar: Downtown
As part of the newly revived Chicago Athletic Association, Game Room takes the original billiards room and reimagines it as a boisterous playground and bar that pays homage to the organization’s clubby past for a new era of competitive smackdowns in bocce, billiard, shuffleboard, chess, and checkers.
12 S. Michigan, https://www.chicagoathletichotel.com/restaurants/game-room
Photo Cred: Thrillist
Best Bar for an Old Chicago Experience Bar: Old Town
This iconic dive bar has become a go-to in Old Town, thanks in part to its 4 am closing time, but also because on any given night, you may see celebrities visiting Chicago (and the nearby Second City), plus its iconic jukebox (stocked with jazz) and the unusual decor all over the walls (crude paintings of celebrities and politicians in compromising positions) really create a memorable experience at the Old Town Ale House.
219 W. North, http://www.theoldtownalehouse.com/


