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.
LessThe Place Under The Delusion That It’s Summer: 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 It’s-Never-Too-Cold-For-Ice-Cream Spot: 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 Place That Won’t Let The Holidays Go: 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 Leave-Me-Alone Spot: 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 “I’m Saving Money This Year” Spot: 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.
The Plant-Based Destination: 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 Pot Pie: The royal pies at Pleasant House Pub in Bridgeport 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.
The Winter Patio: 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.
The Unexpected Windfall Celebration: 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.
The Fireplace: 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.