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The Chicago Winter 25

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The Chicago Winter 25

Chicago’s best season is winter. No, it’s not the easiest, but summer doesn’t affirm our resilience like this frigid time of year—when rooftop curling, spicy Thai curries, and fireplace-lit bars prove the city’s mastery of its elements. Here are 25 wintertime ways to make Chicago as much fun as tourists think it is in June.

Chicago’s best season is winter. No, it’s not the easiest, but summer doesn’t affirm our resilience like this frigid time of year—when rooftop curling, spicy Thai curries, and fireplace-lit bars prove the city’s mastery of its elements. Here are 25 wintertime ways to make Chicago as much fun as tourists think it is in June.

photo credit: David Borzkowski


There’s pretending it’s not winter, and then there’s outright denial. Summer House Santa Monica fully commits to its name. Why move to LA when you could go to Lincoln Park for two hours to drink rosé and eat kale salad and fish tacos in a place decorated like a beach house?

The white and airy interior of Summer House Santa Monica. There are green hanging plants, light wooden tables, and white woven chairs.  The ceiling is a skylight.

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photo credit: Stephen Hamilton


Freezing weather can’t deter the real ice cream diehards from getting their hands on the goods. If your lust for ice cream knows no scoop-limit, get the 25-scoop Royal George sundae from Margie’s. Served in a punch bowl, it comes with whatever toppings you want, whipped cream, cherries—plus, a crown of sugar cones because why not?

The 25-scoop Royal George sundae from Margie’s. Served in a punch bowl, with fudge, whipped cream, cherries—plus, a crown of sugar cones.


There are festive restaurants and bars. And then there’s Butch McGuire’s. This Irish pub doesn’t f*ck around when it comes to tinsel, toy trains zooming in the rafters, and giant Christmas mobiles. And unlike your friend with the yearlong Christmas tree, they intentionally keep all of this up for months.

The interior of Butch McGuire’s covered in hanging holiday lights and decorations.
The interior of Butch McGuire’s covered in hanging holiday lights and decorations.

photo credit: Nightshade


After spending all of December at end-of-year work parties and get-togethers with relatives, you might need some alone time. But rather than being cooped up at home, grab a cocktail at Nightshade. It’s in a dark basement, so it’s the perfect place to hide from light-hearted questions like, “How are you going to continue the family bloodline?”

The dark interior of Nightshade, with long teal banquet booths with black round tables.

photo credit: Kim Kovacik


Student loans are back, but you can still eat out and make a dent in the interest payments by loading up on arepas and a cachapa at El Rincón De Fabio in Uptown. Or, for $16, you can get a giant Venezuelan sampler plate, which includes a side of unsolicited instructions on the best way to reheat a chicken empanada and pork patacon.


We’re not going vegan in 2024 since “reviews steakhouses'' is part of our job description—but if you are, kick things off at XMarket. The seven vendors in this plant-based food hall serve everything from mushroom tacos to vegan sushi to Italian “beef.” Plus, its grocery section is convenient if “cook more” is also on your checklist this year.


The royal pies at Pleasant House Pub in Pilsen are like edible alternatives to hot tub boats floating down the Chicago River. Both will soothe your body and warm your hands after a day spent in an office with the thermostat set to 68. But only the rich beef stew or chicken balti topped with flaky, buttery crust will warm your heart.


Filling your living room with Home Depot’s entire ficus supply is one way to create an oasis, but we suggest a visit to Aba’s heated rooftop lounge instead. This sceney Mediterranean spot in Fulton Market serves short rib hummus to go along with a view of the Willis Tower, in a space that looks like Hallmark’s holiday version of FernGully.


Whether it’s your bonus check clearing, expecting an unusually large tax refund, or managing to get out of bed, there are plenty of reasons to celebrate in January. Head to Kyoten Next Door for a special occasion omakase. At $159, you’ll have enough money left to buy that A.I.-powered cashmere sweatsuit you’ve had your eye on.


This Logan Square spot has not just one, but two fireplaces. Throw in some gin cocktails and free, warm cookies (a midnight special), and it doesn't take much convincing to hang out at Scofflaw instead of doing anything that requires a coat.

photo credit: North Pond


North Pond is named after that large puddle in Lincoln Park where couples stage paparazzi-style engagement photos. The restaurant’s cabin-like space is perfect for eating cocoa tea quail, staring out at the park, and watching snow fall as you contemplate whether the nearby zoo’s green tree pythons ever feel hygge.

The Spot Where You Can Say, “Wow, Snow Sure Is Pretty” image

photo credit: Jack Li


If your mood largely relies on sunlight, it can be tough when the sun keeps clocking out before 5pm. But that’s where Provaré comes in—based on (highly unscientific) research, this Creole-Italian spot’s lights emit approximately 127k lumens, a.k.a. the brightness of the sun. Plus, the chicken parm, throwback jams, and refreshing cocktails are just as invigorating as vitamin D.

photo credit: Kim Kovacik


When it’s nine degrees outside, find comfort in an Old Fashioned from the Violet Hour. Sitting with your impeccably balanced cocktail, you’ll feel like the height of sophistication as you bask in candlelight in a room full of floor-to-ceiling velvet curtains. Deep thoughts and leather-bound books are optional.

An old fashioned sitting on a black napkin on a white marble tabletop next to a lit fireplace.


The One-Two Punch


Snow-covered sidewalks aren’t quite as harrowing as dodging skaters at Maggie Daley Park, but both make us want to visit Stay and Play Game Cafe to avoid the danger. For $5, you can play 600+ board games. Plus, there’s a long menu of rum-based cocktails and Puerto Rican dishes to keep you going after you remember that Monopoly ruins lives.

photo credit: Meadowlark


The Meadowlark embodies the coziness of a weighted blanket. It feels like a clubhouse, with comfy couches and World’s Fair-themed cocktails like a toasty, rye-based hooded island. They don’t have a fireplace, but don’t worry—the space’s amber lighting creates such a strong illusion of warmth, you might even be tricked into sweating.

The dimly lit interior of Meadowlark. There is a long bar to the right and black leather seating to the left.


After shelling out hundreds of dollars, braving 90/94, and then discovering your flight is canceled after TSA threw away your shampoo, only one thing will cheer you up. A visit to Dell’Rooster in West Town, with its sunny yellow walls, chicken murals, and a plate of plantains and oxtail to faceplant into while you wait for the next available flight, three days later.


When a surprise snowstorm saves you from meeting out-of-town friends at Navy Pier, just stay on your couch and order Tuk Tuk Thai. Their rich curries, hearty noodle dishes, and papaya salads aren’t just loaded with flavor, they’re also spicy enough that you might need to turn down the thermostat.


Your friends migrated south like a flock of goldfinches but “forgot” to invite you. Plan how you’re going to get better friends this year over margaritas and short rib quesadillas at Costera. It’s a clubstaurant that self-identifies as a Tulum party spot, with palm trees and enough rope on the ceiling for a legion of double-dutch teams.

photo credit: Jack Li


Just the sight of a steaming bowl of bún bò huế from Cafe Hoang will relax you. After one spoonful of the spicy soup, you’ll want to dip your whole body in the hot pool of lemongrass-scented broth, complete with giant meatballs, pork and beef, blood tofu, and noodles as your floaties.

A bowl of Bun Bo Hue

photo credit: Kim Kovacik


Whether you watch the Super Bowl for the game, the commercials, or because you’re waiting with bated breath for Lil Jon to pop up during Usher’s performance, do it with wings from Bird’s Nest. The sauces are zesty (especially the peppery house hot sauce) and the chicken is always crispy-yet-juicy.

photo credit: Kim Kovacik


The brussels and kale salad from Blue Door Farm Stand in Lincoln Park can’t help you curb your Shein addiction or your toxically positive personal brand posts on LinkedIn. But it can help your nebulous commitment to “try new things,” like maple tahini dressing.


Need a spot where you can stare lovingly at someone and say the cheesy things you normally keep in your head? Geja’s, with its fondue pots and campy red interior, is the perfect backdrop for that. And the 58-year-old restaurant is conveniently located in Lincoln Park, so you can continue your romantic montage next to the lions’ den at the zoo.


The phenomenon known as “Fake Spring”—that random 55-degree day in February—is a rare blessing. When it does happen, make the most of it with a trip to the 75-year-old Superdawg in Norwood Park. Roll down your windows, open the sunroof, and head to their drive-in for a Chicago dog, some fries, and a milkshake.

photo credit: Kim Kovacik


Go ahead, embrace your inner Canadian and try your hand at curling on Kaiser Tiger’s winter patio. Bring some friends, share beer and sausage, and enjoy a sport that proves exactly how bored and desperate winter can make people.

A curling rink in an enclosed tent with hanging twinkle lights and a banner that reads, "Kaiser Tiger & Misguided Spirits."
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