Food & Drink

The Best Winter Day-Drinking Bars in Chicago

Published On 01/10/2017 Published On 01/10/2017
rose's lounge chicago
Rose's Lounge | Sean Cooley/Thrillist
Monk's Pub Chicago

Monk’s Pub


Day drinking doesn’t have to be a strictly local affair. And while summer offers the perfect excuse to ditch work to go boating, if you’re playing hooky in the winter to drink beer you thankfully don’t have to travel far. Take an “extended meeting” at this long-running Downtown den of Old World-style wooded décor modeled after a monastery the owner once lived in as a boy. Also known as one of the finest places to grab a burger Downtown, this warm, inviting space of dusty old kegs and heady Belgian brews is as easy to access as it is hard to hate.

Rossi’s Liquors

River North

One of the last bastions of weirdness in the increasingly corporate conglomeration that is River North, Rossi’s is tailor-made for day drinking in winter. It’s the perfect kind of dark dive you enter to shut out the world behind you and replace it with a no-frills, cash-only utopia where you make your selections from a fridge of beers and turn to grouse about local politics with an intriguing cast of characters ranging from grizzled old timers to lost tourists. And in case mid-day drinking isn’t early enough for you, they open at 7am.

Flickr/Bill Couch



As one of the best beer bars in the country and one of 50 Chicago bars to drink in before you die, Hopleaf is already the stuff of local legend. But if for some reason you have yet to visit this Andersonville institution known for its heavy-hitting selection of Belgian beers and perennial favorite bar dish of mussels and fries, winter is the perfect time to get acquainted with this friendly neighborhood hangout. While it makes a damn fine visit any time of year, Hopleaf’s cozy confines seem most fitting when the weather is cold and the snow outside is piled high.

Annie Kostiner


Lincoln Park

With a spacious front lounge of books and newspapers opening up to a fun back room stocked with games and a foosball table, this newish Lincoln Park “bookbar” seems to have been designed specifically with winter in mind. With a goal of “preserving face to face communication,” Chicago’s first “Wi-Fi-free hangout” offers beer, wine, and slow-brewed coffee in addition to a small menu of cheeses, Chicago-style hot dogs, and ice cream. Just around the corner from a booze-serving movie theater and deep-dish kingpins Pequod’s, it’s the ideal destination to hunker down for a Sunday Funday and wait out the storm.

Moody’s Pub


As one of Chicago’s top fireplace bars, Moody’s Pub is a wintry ski-lodge-like paradise of massive charbroiled burgers and warm-up drinks like the Moodymint (peppermint schnapps and hot chocolate topped with whipped cream) designed to bring you in from the cold. The medieval-style fortress that looks like a church from the outside has only been around since 1959, but feels like the kind of place a medieval knight might choose to day drink casks of mead. While the excellent back patio may not be the most conducive to winter drinking, the bar’s twin fireplaces, stained glass, and candlelit tables make for a perfectly acceptable romantic-without-trying-too-hard winter Tinder date locale.

Rose’s Lounge

Lincoln Park

We feel pretty confident in the fact that we’re not breaking any news with the following declaration: Winter in Chicago sucks. But when times get tough, you can always turn to grandma for some homespun creature comfort. Especially when that grandma happens to be Rose, the Macedonian matriarch of this long-established neighborhood dive (and one of the best dives in America) who lives upstairs. Stop by for frosty mugs of Old Style, year-round Christmas lights, and well-worn couches in a fun basement party vibe that feels like your parents are out of town and they left your cool grandma in charge.

Flickr/Joselito Tagarao

Map Room


This self-described “traveler’s tavern” is the perfect place to impress the hottie at the next barstool with your geographic prowess by locating Azerbaijan on the map on the wall or correctly identifying the Brazilian flag on the ceiling. As of one Chicago’s finest beer bars, it’s also a terribly enticing location to spend a wintry day paging through weathered copies of National Geographic while exploring a ridiculously long beer list like the Marco Polo of a boozy Saturday afternoon. They also offer continuing education in the form of their beer school program, so the more brain cells you kill the more you learn.

Courtesy of Twisted Spoke

Twisted Spoke

West Town

From the weird motorcycle art out front to eight varieties of Bloody Marys to the “Smut & Eggs” late-night breakfast porn party, Twisted Spoke is known for many things. And in addition to its crazy-balls nachos and fried poppers, it’s also known as a prime day-drinking spot that will never let you down. So while its rooftop patio is more of a summer tradition, some things work just as well in winter... like working your way through a stacked menu of 300+ whiskeys as you calmly watch winter rain shit on Chicago through the windows.

Logan Arcade

Logan Arcade

Logan Square

No one would fault you for wanting to wait out the next Polar Vortex in your new Cubs Snuggie, drinking beer and playing video games all day. But you can also do pretty much the same thing at Logan Arcade, featuring the city’s largest public collection of pinball and video games plus the 10-player Killer Queen -- which has reached something of a mythical status amongst the city’s gaming nerds. You can also attend socially conscious events like fundraisers for the ACLU and Oakland fire relief while making your way through a massive selection of hipster-approved craft brews. Hell, wear the Snuggie if you feel like it.

Rite Liquors

East Village

Just as culturally relevant as deep-dish pizza and corrupt politicians, the Chicago bar/liquor store combo known as the slashie is a glorious yet criminally underrated aspect of local culture. And winter is when they really shine. Such is the case at Rite Liquors, which clings to its craggy old man bar aesthetic despite the encroaching gentrification surrounding it on all sides. With little more than a long bar with a pool table at the end opposite a checkout counter for newspapers and to-go booze, this erstwhile establishment is your winter home base for watching the short daylight hours evaporate as you play scratch Lotto tickets and commiserate with perhaps the most beautifully random assortment of mankind ever assembled.

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1. Monk's Pub 205 W Lake St, Chicago, IL 60606

Since 1978, Monk's Pub has been pouring an extensive, international selection of craft brews and a dozen different juicy burgers from its post in the Loop. Decorated in the style of a classic European pub -- accented by antiques like kerosene lanterns, vintage books, and spent wooden barrels -- Monk's is a warm, neighborhood joint with charm, character, and a chili-beer cheese cheeseburger worth writing home about.

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2. Rossi's Liquors 412 N State St, Chicago, IL 60610

In a forest green storefront on North State St., with signs advertising fine wines and packaged goods, Rossi's Liquors is a River North mainstay. The store is home to a selection of beers, wines, liquors -- fine, and otherwise -- and to a dark, unpretentious bar oft patronized by those in search of a post-work drink. Rossi's is a welcoming, neighborhood dive where the lights are dim, the jukebox constantly rocking, and the drinks cheap enough that it's easy to get lost in your own thoughts.

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3. Hopleaf 5148 N Clark St, Chicago, IL 60640

This Andersonville beer bar is known for its rotating selection of draft beers primarily from the Midwest and Belgium. More than just a bar that serves food, Hopleaf has an outstanding menu of Belgian-inspired food like mussels from Prince Edward Island, charcuterie, and steak frites. The place is casual and laid-back, just like a neighborhood bar should be.

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4. Kibbitznest Books, Brews & Blarney 2212 N Clybourn Ave, Chicago, IL 60614

Kibbitz is a Yiddish term meaning “to chat in an informal, friendly way.” It should come as no surprise, then, that Kibbitznest Books, Brews & Blarney in Lincoln Park is a wifi-free (gasp!) place to chat with friends in a hybrid bookstore, cafe, and bar. The bookstore features both new and used liberal arts books, the cafe and bar features lounge chairs, couches, and communal tables for socializing over a pint of beer, a cheese plate, or a glass of wine. There’s a reading room for those looking for a quiet evening with a book, games for those looking to interact with others, and typewriters for those looking to write mom and dad a letter the old fashioned way. Leave your laptops at home; Kibbitznest is reserved for human (or book, or beer) interaction only.

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5. Moody's Pub 5910 N Broadway St, Chicago, IL 60660

Step behind the heavy, wooden door of Moody’s Pub, and into its ski lodge-reminiscent dining room in Edgewater for cheap drinks, locally acclaimed cheeseburgers, and free peanuts. The pub, born in 1959, features two fireplaces, oak wood tables, stained glass windows, and beamed ceilings, lending to the cozy, lodge-like atmosphere. During the few weather-permitting months, an enormous and extravagant (there are waterfalls and ivy-lined brick walls) beer garden fills up fast with pub goers, but in the winter, it’s the roaring fires indoors that draw the crowds. And the cheeseburgers, pitchers of sangria, and wallet-friendly prices, of course.

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6. Rose's Lounge 2656 N Lincoln Ave, Chicago, IL 60614

Through the screen door of Rose’s Lounge in Lincoln Park, you’ll find mismatched lounge chairs, couches, and dining room table sets, wood-paneled walls, and christmas lights year-round for a pop of light and color in an otherwise musty, basement-reminiscent dive bar. It’s been run by a woman named Rose since the late 70s, which seems to be the last time the bar’s interior was designed. The mugs are frosted for your pints of Old Style, which run for just a couple dollars, and is the perfect beverage to pair with a game of billiards.

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7. The Map Room 1949 N Hoyne Ave, Chicago, IL 60647

With flags and world maps decking the walls, Bucktown's The Map Room is a self-described "traveler's tavern." Appropriately so, it's a drinking destination for any beer geek passing through Chicago. Since opening in 1992, the bar has struck up deep ties in the brewing community, and the rare and varied brews on its insanely long beer list are proof of its status as a beer mecca. The Map Room takes tastings to the next level with "Beer School," a 20-plus year tradition hosted by various brewmasters that will teach you everything you need to know about beer.

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8. Twisted Spoke 501 N Ogden Ave, Chicago, IL 60642

In case the exterior motorcycle art and bike handlebars on the front door didn't tip you off, Twisted Spoke is a biker bar. The West Town hangout is beloved by Chicagoans of all stripes thanks to a massive selection of whiskey and beer, legendary Bloody Mary menu, rooftop garden, and sinister bites like barbecue nachos and fried jalapeño poppers. Of all the things that make Twisted Spoke stand out though, it's the weekly Saturday night "Smut and Eggs," when you can order breakfast food and watch porn. Um.

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9. Logan Arcade 2410 W Fullerton Ave, Chicago, IL 60647

Located in the original Logan Hardware building, this arcade/bar houses a collection of vintage pinball, video games, and serves up 20 quality draft beers and a large selection of other alcoholic beverages.

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10. Rite Liquors 1649 W Division St, Chicago, IL 60622

In a space once occupied by a polka club in the 1920s, Rite Liquors has been operating as a liquor store and dive bar since the 70s. With an ample selection of things to do and consume -- like scratch off the lottery tickets you couldn’t help but buy, drink cans of Busch Light paired with a bag of chips or a Hostess cake, and grab a pack of smokes for the road. It’s like an old gas station in stock selection and fluorescent lighting, a dive bar in atmosphere (the lights dim as you travel to the back towards the bar), but above all, a liquor store with a selection you may not expect from a dark, neon-lit corner store.