Chicago’s best wintertime bars

When the weather outside is frightful, sneak inside to enjoy a drink at these favorite establishments

Just because the weather dips below freezing and the snow starts falling doesn’t mean your social life has to come to a grinding halt. Between wintery cocktails, holiday decorations and a roaring fireplace, it can still be plenty of fun to venture out to the right establishment.

The Real Chicago polled readers from all over the North Side for their favorite bars to frequent during the winter season. From Irish pubs to wine bars and lounges, we think they’ve got it covered.

What follows are direct quotes from our readership, in no particular order. Bundle up and enjoy!

Matisse (674 W. Diversey)
“It’s a bar that is located in a lower level, so cold air doesn’t get in very easily. It also has a cold-month atmosphere with dark red walls, dim lights and a fireplace. It’s a less congested bar, which is what I tend to look for in a bar during the winter. It has great weekly specials too.”

Schubas (3159 N. Southport)
“What is better to ward off winter doldrums than a quaint bar full of holiday cheer, great live music performed nightly, awesome holiday decorations that make you feel at home, an ample beer and liquor selection and, of course, a wonderful and friendly staff?”

“Schubas, it just looks like it is warm.”

Jack’s Bar & Grill and the 404 Wine Bar (2856 N. Southport)
“I recommend sitting by the fireplace and ordering the chicken pot pie.”

“Extremely friendly neighborhood bar. Very classy too. You can watch the game and have a pint at Jack’s or walk into the 404 and enjoy a variety of wine on a couch or a candle-lit table. It really is the best of all worlds. Great place to have a date or catch up with friends.”

Wilde Bar & Restaurant (3130 N. Broadway)
“A new addition to the Lakeview area, just a month old, Wilde offers a homey feel, which is perfect for the winter months. At the center of the bar is a raised, candle-lit sitting room with a fireplace, stacks of books and a painting of Oscar Wilde himself, the bar’s namesake. It feels like you’re in a country English home. The elegant pub serves up classic Irish and English dishes. Throw down some cold, freezing rain, and you’ll feel like you’re in London. The bar isn’t some swanky pushover either — it’s open until 4 a.m. every night and 5 a.m. Saturday night with a DJ and dancing.”

Cullen’s (3741 N. Southport)
“I really ike Cullen’s on Southport this time of year. The decorations are beautiful, with Christmas lights everywhere — very cozy.”

“I love Sunday nights there. Great holiday lights, and the staff is always friendly and eager to please.”

Bungalow Lounge (1622 W. Belmont)
“Bungalow Lounge used to be one of our favorites. I would go with the girls to get vanilla martinis and sit at the high tables or booths in front of the fireplace. I think they’ve changed ownership, so I’m interested to go back to see if they can still make a vanilla martini.”

The Violet Hour (1520 N. Damen)
“I really like the Violet Hour in Bucktown. It’s styled like a speakeasy, with chandeliers, high-backed leather chairs and a no-cell phone/no-smoking policy. The drinks are all $11 each, but they are all old-time, traditional recipes mixed with care by the bartenders, and more than two will knock you out. Good place to go with a small group — not a great place to mingle though.”

Old Town Ale House (219 W. North)
“If pornographic art and the sound of Nina Simone’s voice doesn’t warm you up, nothing will. Try to snag a tight-but-cozy table by the window so your group can enjoy peering through the steamy windows at all the suckers standing out in the cold. Just make sure to bring enough quarters for the jukebox and an appetite for old jazz and soul.”

Southport City Saloon (2548 N. Southport)
“It not only has the best beer garden in the city to enjoy during the summer, but the bar and dining room with the low lighting and fireplace make it easy to enjoy when it’s cold outside too. They may have the nicest selection of decorations and lights I’ve seen. Really tough to leave.”

Will’s Northwoods Inn (3030 N. Racine)
“Nothing beats the feeling of being in the north woods in the middle of winter without having to really feel the cold of the north woods. If I had a choice, I would go to a friend’s house and chill, play games and sit in front of a fire, but Will’s is a close second.”

Moody’s Pub (5910 N. Broadway)
“It’s always toasty warm, and you can barely see anything in there. Great first/blind date place. Your date’s personality will shine right through, hopefully, and if they end up to be cute, even better.”

Waterhouse (3407 N. Paulina)
“It’s perfect, right off my El stop. It’s a warm and very inviting lounge that makes it easy to want to stay all night. Good food, great specials, laid-back staff. Sit at a table for two or crowd a group into a big booth. And try their sangria. It’ll almost feel like summer.”

D.O.C. Wine Bar (2602 N. Clark)
“I like D.O.C Wine bar because it has a fireplace and is cozy. I haven’t eaten there, but I hear it has good food too.”

Garret Ripley’s (712 N. Clark)
“I like Garret Ripley’s. It’s a great pub — the dark wood and Christmas decorations give it a warm, homey feeling. Great beer selection and upscale bar fare.”

The Matchbox (770 N. Milwaukee)
“Smallest bar in Chicago. Cozy place. Awesome drinks, and you never know who you will sit next to. Could be a biker, stock trader, regular joe.”

Guthrie’s Tavern (1300 W. Addison)
“It feels just like home to rummage through their delivery menus and ‘order in.’ ”
“Awfully fun place, but get there early to get a table and the board game of choice. The lamps on every table are cool. It feels like a ski lodge to me.”

“Guinness, tables too close for the fire marshall’s comfort and Battleship. Great place to bring a group of friends, just to have the friendship tested over an intense game of Risk. The place is usually packed, so getting there earlier in the evening is key. It’s easy to challenge the next table to a game or invite new arrivals into a game for a share of your table. Something different than the same ol’ bar scene.”

Matilda (3010 N. Sheffield)
“I love the way the place is decorated, and the juke box and wine selection are fantastic.”
“Don’t forget about the funky Baby Atlas room downstairs, which is great for a private party. The big windows upstairs are nice to sit next to and sip cocktails.”

Duffy’s Tavern & Grill (420 W. Diversey)
“I’m partial because of its location, good food and euchre leagues. Winter is especially card-playing season, and what better way to spend a cold winter Monday night than to play euchre with friends.”

Grace O’Malley’s (1416 S. Michigan Ave.)
“Grace O’Malley’s in the South Loop is a great place for the wintertime blues. Grace’s is decorated with a perfect Christmas cheer ambiance. The clientele and staff make you feel comfortable, and the food and drinks are excellent. Well-attended by Bears fans after a cold game for a nice pint of Guinness.”

Clark Street Ale House (742 N. Clark)
“The bar staff makes you feel at home and part of their family. They have a great selection of scotch if you’re looking for quality labels and plenty of seating.”

Vintage Wine Bar (1942 W. Division)
“Warm, cozy atmosphere with a fireplace and good wine selection.”

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