1. Grab some cozy layers. Chicago isn’t too cold — you’re just not dressed right. And dressing right is an art as much as it is a puzzle. It’s a puzzle I relish each winter: Body layers, midweight layers, top layers, hat and a scarf. (Tip: Doesn’t need to be that thick to be effective — I use a thin merino wool scarf from IceBreaker for most of the winter.) Dressed right, you’ll complain about the cold, but far less than those who simply put on a down coat and figure they’re good to go. — Josh Noel
2. Embrace the boot. I’ll be pulling out these perfectly stylish, streamlined Uggs (Simmens leather waterproof boot with wool upper, $170 at Nordstrom) that get the job done on most Chicago days. But if we get another Blizzaster, it might be a good excuse to splurge on these fab-meets-almost-practical suede boots from Moncler ($1,740 at Neiman Marcus). — Amalie Drury
3. Become an urban explorer. Once you’re warm and bundled, get out there and enjoy this beautiful city. (On a bright winter day or after a fresh snow, it’s arguably more beautiful than in summer.) Restaurant sidewalk patios disappear in winter, which returns the streets to the walkers and explorers. I particularly enjoy combing the old industrial streets of the West Loop: See the neighborhood now before the boom of recent years erases old Chicago forever. Then don’t be afraid to admit you’re ready for the right kind of warmup: Stop in at Little Goat’s bakery (adjoining the diner) for great coffee and baked treats on a morning walk, or a delicious cocktail on an evening walk — pick up a crusty baguette to carry home for dinner too. — J.N.
4. Do a deep museum dive. Escape the chill with an afternoon at the MCA’s surrealism exhibit (“Surrealism: The Conjured Life,” Nov. 21 to June 5), where I’ll take my time and really soak it all in, then ponder the weirdness some more over hot chocolate in the museum’s quiet, light-filled cafe, a hidden treasure in its own right. — A.D.
5. Slide down a hill. Take your favorite little kid for a morning of gentle first-time sledding at Cricket Hill (near Montrose Harbor) on a weekday when all the big kids are in school. And since you’ve already called a snow day, make your winter time off count by jumping on that sled yourself. It’s as much fun as you remember. — A.D.
6. Swill the booziest beers. I’ve been squirreling away special beers all spring, summer and fall — or longer. Thick, high-octane beer can be wonderful year-round, but when the weather outside is frightful, that warming booziness is extra delightful. I already have dates planned with Firestone Walker’s Sucaba (a sweet, boozy barley wine aged in bourbon barrels) and Goose Island’s Bourbon County Vanilla Rye (an imperial stout, also aged in bourbon barrels) for short winter afternoons. Didn’t lay in your own supply before the cold hit? Head to Beer Temple for one of the city’s best selections of big beers. — J.N.
7. Toast as if it’s the tropics. Pretend you’re on a tropical vacation by overdoing it on fruity cocktails at Lost Lake. It’s not the beach but it’s … well, lots of rum and really pretty fruit in Logan Square. — A.D.
8. Make a beeline for the fire. My version of “sitting in front of a roaring fire:” Date night at Lincoln Square restaurant Gather, where you can perch at the kitchen counter and feel the heat coming off the stovetop flames as you watch the chefs cook your dinner up close. Order the miso-glazed crispy Brussels sprouts for sure. — A.D.
9. Do sock feet like you mean it. Clean feet in thick, wool socks offer the inverse of one of summer’s joys — flip-flops. In the right pair of wool socks (wool is key: I generally favor SmartWool or Vermont’s Darn Tough), your feet will be snuggled into wintertime heaven. Good excuse to sock-skate around the house all day. — J.N.
10. Find the steamiest possible spa day. Hang out in the super-hot confines of Chicago’s first coed hammam (Turkish-inspired steam bath) at the Virgin Hotel. It’s the place to go when you realize your toes have basically been numb for four days solid. I’ll sip a glass of wine and keep my towel on — because, you know, it’s co-ed. — A.D.
11. Get up close with the ice. Visit Promontory Point — most people have no idea how gorgeous the lake is in winter, and the Point offers a front row seat to the beauty. Except for dog walkers and the hardiest joggers, it’s largely abandoned in winter. — J.N.
12. Get your holiday cheer via the CTA. Know a kid who loves trains? If so, or even if you’re just a big kid at heart, don’t forget to keep your eyes peeled for the CTA holiday train. Or go all-in at the Chicago Botanic Garden’s Wonderland Express. — A.D.
13. Ski, flatlander, ski! Colorado is wonderful, but the hills of Michigan and Wisconsin are unpretentious and nonjudgmental. A ski expert? You can own these hills. Just learning? The Midwest is the perfect place. Boyne Resorts in Michigan is the gold standard, but I have also enjoyed Michigan skiing at Crystal Mountain and even itty-bitty Wilmot Mountain (which is really more of a hill) just over the border in Wisconsin. — J.N.
14. Own the Super Bowl. Even if you don’t care about football, this quasi-national holiday is a good excuse to get together with friends in the depths of winter in someone’s warm living room. A friend once brought her knitting to my Super Bowl party precisely because it was a good day to hang out, if nothing else. Hosting? Treat your pals to fantastic barbecue takeout from Lillie’s Q or Smoque. And if you’re a guest at someone else’s party, that same barbecue works wonders in the “what can I bring” department. — J.N.
15. Make lunch an occasion. Gather your friends for a soon-to-be-annual winter lunch at a great restaurant. I’m lucky enough to have a yearly invite to one held upstairs at Le Colonial — we show off our winter style, eat a big family-style meal and drink Champagne all afternoon, then some of us adjourn to the bar for another hour or two. — A.D.
16. See Millennium Park from the other side. With any luck, there’ll be snow when you experience Millennium Park’s Pritzker Pavilion from the cozy confines of the stage itself, where you can hear cabaret-style concerts by Lyric Opera’s big stars and rising talents during the Harris Theater’s intimate Beyond the Aria series. They close the big glass “curtain,” so the stage is nice and toasty — unlike the big, empty lawn. You can reserve table seating for $150 or sit in the choral risers for only $40. — A.D.
17. Take breaks. Get the heck out of town, and go somewhere warm. I’ve been to Mexico, Belize and Hawaii during recent winters. But there’s no need to go too far; South Florida or San Diego work too. This winter? Back to Mexico, and my first visit to the Riviera Maya. — J.N.
18. Relish silence in the city. I can’t wait to soak in the hush after the first big snowfall. Summer was so loud — from construction everywhere to low-flying jets to amped-up concerts (AC/DC at Wrigley ring any bells, Lakeviewers?) I can’t wait for a serious accumulation of snow that makes everything go silent for a little while. You can walk down the middle of the street, and all is clean, quiet and white. Shhhhh, city. — A.D.
![“Let the music do the talking,” sang Phish vocalist-guitarist Trey Anastasio at the outset of the band’s concert Saturday at the Sphere in Las Vegas. Normally, hearing that advice from a well-disciplined virtuoso who seemingly never tires of the stage and worships the groove would pass without a hint of potential irony. However, given the group was not even one minute into the third of its sold-out four-night stand at the $2.3 billion dome — expressly devised to push sensory boundaries to previously uncharted limits — one couldn’t help wonder how seriously Phish would take its own instruction. Turns out […]](https://www.chicagotribune.com/wp-content/uploads/2024/04/CTC-L-ENT-PHISH-04-e1713888536637.jpg?w=620 "“Let the music do the talking,” sang Phish vocalist-guitarist Trey Anastasio at the outset of the band’s concert Saturday at the Sphere in Las Vegas. Normally, hearing that advice from a well-disciplined virtuoso who seemingly never tires of the stage and worships the groove would pass without a hint of potential irony. However, given the group was not even one minute into the third of its sold-out four-night stand at the $2.3 billion dome — expressly devised to push sensory boundaries to previously uncharted limits — one couldn’t help wonder how seriously Phish would take its own instruction. Turns out […]")