As soon as the first sprinkle of snow falls, cozy season in Chicago officially begins.
The city celebrates the art of coziness in so many ways: Picture steaming saunas along the lakefront, candlelit jazz bars that glow against the cold, and tucked-away taverns where you can sip warming cocktails by the fire.
Here’s our guide to celebrating winter in Chicago with snug, inviting experiences that will make you fall in love with the season.
Cozy Chicago activities
Float in Roman-inspired baths
Take a dip in thermal pools and salt baths inspired by ancient Roman, Greek, and Ottoman traditions at AIRE Ancient Baths. The stunning space is housed in a converted industrial loft from the 1920s, filled with soft candlelight. You can also schedule a massage or soak up the warmth in eucalyptus-scented steam rooms.
@choosechicagoFile this under “perfect ideas for Valentine’s Day.” ❤️ Whether you’re treating yourself, your significant other, your mom, or anyone else this Valentine’s, the luxurious AIRE Ancient Baths couldn’t be a better way to celebrate. 💧 Here are some offerings you can expect: Hot, warm, and colds baths, plus a cold plunge, multiple steam rooms, a floatarium (salt water pool), indoor-outdoor bath, and more! 📍 AIRE Ancient Baths 800 W Superior St♬ Peaceful Night – Relaxing
Dine by a roaring fire
Chicago’s dining scene offers plenty of cozy hideaways where you can enjoy dinner and drinks fireside.
Lady Gregory’s in Andersonville is a neighborhood favorite with a cozy fireplace, hearty pub fare, and an extensive whiskey list. Locals linger here for hours in the wintertime.
Styled like a 1920’s London pub, Armitage Alehouse in Lincoln Park has a wood-burning fireplace that pairs perfectly with belly-warming pub staples.
Moody Tongue Brewing Company in the South Loop features chef-driven dishes and signature brews best sipped by the sleek fireplace.
Tucked away in a historic hotel, The Drawing Room bar and restaurant is a stately space with massive stone fireplaces and a sophisticated atmosphere.
Enjoy an intimate music venue
Winter nights are made for evenings at Chicago’s coziest music venues, like these dimly lit jazz bars and clubs.
The Green Mill in Uptown, where the lights are low, the music is lively, and the atmosphere is drenched in history. Snag a seat at the bar or grab your partner and take a spin on the dance floor.
You’ll also find warmth and rhythm at Rosa’s Lounge in Logan Square, a legendary blues club beloved for its authentic performances.
For a touch of elegance, Jazz Showcase in the South Loop offers world-class acts in a small but storied setting that has hosted legends.
In Humboldt Park, The California Clipper is a former speakeasy known for its signature red lighting and musical acts that range from jazz to country to everything in between.
Sip hot chocolate
When the chill sets in, nothing feels more comforting than a cup of rich hot chocolate in the city.
The renowned Mindy’s Bakery in Wicker Park serves its decadent hot chocolate with house-made marshmallows. Make sure to get a pastry on the side.
In Logan Square, Katherine Anne Confections offers European-style drinking chocolate in flavors like Salted Caramel and Mexican, featuring a blend of cinnamon, cayenne, habanero, and guajillo chiles.
Sweet Drip Dessert Café is a Hyde Park gem known for creative cocoas that can be paired with sweet waffles and crepes in a cozy, Instagram‑worthy atmosphere.
Shop cute bookstores
Chicago’s independent bookstores are perfect for a cozy afternoon of browsing and discovery.
In Roscoe Village, The Last Chapter Book Shop offers a cozy space where curated shelves invite you to linger over the latest romance reads.
In Andersonville, Women & Children First is beloved for its thoughtful reads and engaging author events.
Enjoy books, brews, and blarney at Kibbitznest, a welcoming bookstore and gathering space that includes a bar and plenty of nooks to hide away with a new read.
In Hyde Park, 57th Street Books welcomes readers down the stairs and into its labyrinth of shelves.
And inside the historic Fine Arts Building, Exile in Bookville offers a fine selection of books with a creative bent.
Learn a new cozy craft
Cozy winter days are best spent leaning into the season’s slower rhythm. Winter is also the perfect time to learn a new-to-you craft.
Learn the art of stained glass at Flan’s Glass in Bucktown, where beginner classes teach students the basics of glass art.
Shape clay into a coffee mug, planter, or decorative plates at Lillstreet Art Center in Ravenswood, which offers all-levels ceramics workshops.
Make your own natural soaps using organic and sustainable ingredients at Abbey Brown in West Town.
Explore more: Check our more crafty classes and workshops in Chicago this winter and beyond.
Check into a cozy hotel
For the ultimate in cozy luxury, check yourself into a Chicago hotel for the night, or better, a long weekend.
At the Four Seasons Chicago, you can indulge in spa treatments, swim a lap then soak in a hot tub, sip cocktails in an intimate speakeasy hidden on the 46th floor, and then pop back into your plush room to make up for all that sleep you’ve been missing out on.
In the buzzy South Loop, The Publishing House Bed & Breakfast is the perfect balance of chic and comforting. Enjoy your beautifully decorated suite or grab a seat by the double-sided fireplace and socialize in the Great Room.
In Hyde Park, the Sophy Hotel is offering special winter packages that include perks like complimentary cocktails and late checkout. During your stay, pop over to the Midway Plaisance ice rink to skate in the shadow of the stunning University of Chicago campus.
Meanwhile, the Waldorf Astoria Chicago in Gold Coast, recent winner of the coveted AAA Five Diamond designation, offers French-inspired elegance with suites that feature in-room fireplaces, a luxury wellness-focused spa, an indoor pool, terrace views perfect for sipping wine after a day of exploring, plus the kind of service that makes you feel completely at (your dream) home.
