It's that time of year again. The holidays. Along with the twinkling lights lining Michigan Avenue and general merriment whistling through the air — and by merriment we mean cocktail lunches and legendary office parties — you’re in store for loads of family time. And, whether that includes posing for family photos in that reindeer sweater Granny insists you wear or explaining your relationship status yet again, hatching an escape plan is a must. Luckily, we’ve rounded up 14 seriously cool activities around Chicago that you'll enjoy with your relatives — or without. So, go ahead, take back your holiday spirit and relish in what really should be the most wonderful time of the year.
The Dawson may be on the border of River West, but we’d be remiss to exclude this new hot spot by restaurateurs Billy Lawless (of The Gage and Henri) and Branko Palikuca (of Topaz and Amber). It's just up the street from the heart of the West Loop and features reinterpreted classic American cuisine. Brave the temps this season by the patio fireplace, as the restaurant launches a weekly Fireside Brewer Series, where it showcases a different craft beer on tap every Tuesday through the end of the year. We also recommend the oversized, meant-to-be-shared cocktails aptly called Vessels — they're so much more than the punch bowls of yesteryear. And, you thought this “family affair” was going to be boring.
The Dawson, 730 West Grand Avenue; 312-243-8955.
Photographed by Patrick Fahrner.
This German-American holiday market is one of our favorite annual traditions. Chicken schnitzel sandwiches, potato pancakes, and warm, cinnamon-coated almonds — what’s not to love? The vendors take over Daley Plaza, setting up mini tents serving authentic German fare, and trust us, it’s worth the calorie splurge. This year marks the 100th anniversary of the city’s Christmas tree, and the 57-foot stunner, with some 29,000 lights and 300 decorations, is worth a cheesy snapshot with your beau. Duck into the warm hut with a ceramic boot mug filled with Glühwein (hot, spiced wine) or shop the selection of holiday goodies: everything from hand-painted ornaments to a candy shop that will have you booking an emergency session with your trainer. Go quick before it disappears come Christmas Day.
Daley Plaza, 50 W Washington Street (between Dearborn, Washington, and Clark Streets); 312-494-2175.
Photo: Courtesy of German American Services, Inc.
There’s not much we love more than strolling through a street market. But, when we hear there’s an opportunity to enjoy seasonal fare without watching our fingers turn to icicles when inhaling a Paulina Meat Market veal brat, consider us sold. The Nosh, Wicker Park’s weekly food fest, heads indoors this winter to Block Thirty Seven, from December 3 to 6, and 9 to 13, at 10:30 a.m. to 2 p.m. Local vendors from all over the city like Bang Bang Pie & Biscuits, Da Lobsta, and Mixteco Grill will be preparing and serving small-batch artisan foods right in the heart of the Loop. Leave your puffer coats at home.
The Nosh at Block Thirty Seven, 108 North State Street (between Washington and Randolph streets).
Photo: Courtesy of The Nosh.
Lunch in Macy's Walnut Room on State Street is a tradition as rich as its famed chicken pot pie. Its seventh-floor dining room, which opened as the first department-store restaurant in 1905, recently completed a renovation that restored elements to their original grandeur. And, now, through December 24, head to the fifth floor for what we’re guessing is a childhood tradition that's fallen by the wayside: a visit with Santa. No, we don't suggest you sit on his lap and explain you’re dying for an Eddie Borgo pyramid cuff. There is something undeniably joyful about watching giddy kids in their holiday best, waiting for their five minutes with the big man. Plus, a photo with (or even near) Santa will surely make a worthwhile #TBT Instagram.
The Walnut Room, 111 North State Street (between Randolph and Washington Streets); 312-781-3125.
Photo: Courtesy of Macy's on State Street.
After months of anticipation, Eataly Chicago is finally opening its 63,000-square-foot space in River North — just in time for holiday shopping. The high-end Italian food market features eight full-service restaurants, an on-site brewery and tasting room, a cooking school, and shelf after stocked shelf of gourmet food and packaged goods. If you’re not cooking Christmas dinner, plan on bringing something extra special for your host with one of Eataly’s gift baskets. La Dolce Vita is packed with chocolate cookies and torrone-hazelnut nougat for that sweet tooth, and The Molto Batali includes a copy of the new Batali brothers' cookbook. With 500 vendors, we could easily get lost in this mini-escape.
Eataly, 43 East Ohio Street (between Rush Street and Wabash Avenue); 312-521-8700.
Photo: Courtesy of Eataly.
Last December, The Peninsula Chicago debuted the only hotel skating rink in town, and this year it's back. Show off your
two-foot spinwobbly teeter-tottering, and then reward yourself for not falling with some hot chocolate, warm pretzels, and delicious beignets. Opening November 23 on the Michigan Avenue-facing terrace, the rink’s gorgeous views of downtown are worth braving the ice. Admission is $10 for adults and $5 for children (12 and under), and all proceeds go straight to the Ann & Robert H. Lurie Children’s Hospital of Chicago and Hephzibah Children’s Association.
Later, head down the street to Garrett Popcorn Shops, and line up for what’s sure to be a worthwhile wait for a seasonal tin of the limited-edition Gingerbread Caramel Crisp. It features the brand's legendary sweet, buttery caramel popcorn that's infused with warm ginger spices. Hey, what's the point of skating without the cozy, post-rink eats?
The Peninsula Chicago, 108 East Superior Street (between Rush Street and Michigan Avenue); 312-337-2888; Garrett Popcorn Shops, 625 North Michigan Avenue (between Ontario and Ohio Streets); 312-944-2630.
Photo: Courtesy of The Peninsula Chicago.
Sometimes you just need a little classic holiday cheer in your life, and the Four Seasons Hotel Chicago provides just that. With its stately decorated tree and warm, inviting respite from the hustle and bustle of Michigan Avenue. From now to the end of the year, warm up next to the fireplace at Allium, where complimentary roasted chestnuts will be offered between 5 and 7 p.m. daily. They'll pair perfectly with the restaurant’s list of specialty cocktails and hot chocolates. Its Jack Frost Martini, made of Stoli Vanil Vodka, Godiva White Chocolate Liqueur, Peppermint Schnapps, and house-made white-chocolate-peppermint bark, is sure to cure the coldest nip.
Allium at Four Seasons Hotel Chicago, 120 East Delaware Place (between Michigan Avenue and Rush Street); 312-799-4900.
Photo: Courtesy of Four Seasons Hotel Chicago.
Sofia kicks off the holiday shopping season with a special 12 Days of Christmas event on December 13 to 24. With daily promotions and in-store events, the Gold Coast boutique is sure to be flooded with shoppers falling in love with its eclectic selection. Highlights include the kickoff Go Bold, Go Gold event, where the gold-plaited salon offers on-site blowouts and makeovers while guests score 10% off all in-store items. And, don't miss the Spend More, Save More discount on December 21 to 23 — the higher the price tag, the bigger the discount. Everyone wins!
Sofia, 100 East Walton Street (between Michigan Avenue and Rush Street); 312-640-0878.
Photographed by Tyler Curtis.
Shopping one of the city’s best selections of new, vintage, and antique finds just gets better in the winter, as the Randolph Street Market heads indoors for its holiday edition. On December 14 to 15, from 10 a.m. to 5 p.m., nearly 100 vendors will display a mix of goods, ranging from home decor, restored furniture, and antique jewelry to vintage mink stoles and fine works of art. This year, the market is adding a photo booth, where guests can pose with the outrageous and hilarious Kit Kat Lounge drag performers between 1 and 2 on Saturday afternoon. We recommend loosening up a bit with some Peppermint Schnapps served at the Holiday Market Bar — it'll make for a Christmas card that's sure to make grandma blush. Tickets are $8 in advance or $10 at the door.
Randolph Street Holiday Market at Beaux Arts Plumbers Hall, 1340 West Washington Street (between Ogden Avenue and Elizabeth Street); 312-666-1200.
Photo: Courtesy of Randolph Street Holiday Market.
On Your Mark Coaching and Training invites you to celebrate the season with its aerobic, strength, and endurance classes — along with some much-needed real talk — to get your cookie-munching tush in shape. (So, you and that third piece of pumpkin pie do meet again.) Complete the 30-Class Holiday Challenge, which involves signing (and showing!) up for 30 classes between Thanksgiving and Christmas Eve for the flat fee of $220. You'll also gain entrance to the Big Reward Class — a special 2.5-hour killer workout open only to winners, err, those who hit all 30 classes.
On Your Mark Coaching + Training, 1101 West Monroe Street, Suite A (between Aberdeen Street and Racine Avenue); 312-733-9330.
Photo: Courtesy of On Your Mark Training.
With Chicago's rich theater tradition, it's really no surprise that there are more than a few holiday shows to take in. Year after year, our favorites are still Goodman Theatre’s rendition of A Christmas Carol (now in its 36th year) and The Nutcracker presented by the Joffrey Ballet, which takes us through a magical land of toy soldiers and a nutcracker prince with all the pomp and circumstance of a perfectly on-point ballerina. This year, we're looking forward to catching Elf the Musical. Much like the 2003 film, it details Buddy the Elf’s travels from the North Pole to Manhattan in search of his father, and the contagious Christmas cheer he spreads along the way.
Joffrey Ballet, 50 East Congress Parkway; 312-386-8905.
Photographed by Herbert Migdoll.
The Lakeview neighborhood may be home to the watering holes of our college years, but it’s also known for an amazing range of boutiques. From local favorites like Cerato, Krista K, and M2 to larger labels like Free People, Lululemon, and Benefit. To welcome you with open arms, the shops and restaurants along the Southport Corridor are decked out in their holiday best with wreaths and pine on every block.
Southport, Southport Avenue from Belmont Avenue to Irving Park Road.
Photo: Courtesy of Southprot Corridor.
Lush Wine & Spirits, one of our favorite neighborhood wine shops, is determined to ensure your family-filled holiday activities don't cramp your style. Between December 25 and January 6, collect all 12 bottles of the shop’s handpicked vinos in the spirit of the 12 days of Christmas, or wrap up the whole lot and head to mom's house with what's sure to be one of the most popular additions to this year's feast. You'll be well-armed to handle any family drama that comes your way.
Lush Wine & Spirits, 2232 West Roscoe Street (between Oakley and Bell Avenues); 773-281-8888.
Photo: Courtesy of Lush Wine & Spirits.
It was Christmas Eve,1983, when a vintage movie palace first showed some old holiday movies and encouraged guests to sing carols during intermission. Now, it's the Music Box Theatre’s annual Christmas Show, December 13 to 24. Imagine this: Rather than a sour ticket-stub taker, Santa greets you at the theater. Then, he leads the audience in carols, as the lyrics are projected onto the screen. Everyone sings, loudly. You sit back, and enjoy old-school classics like It’s a Wonderful Life and White Christmas, while indulging in the buttery goodness of the 21st century’s artery-clogging movie popcorn. Just don’t forget to silence your phone. Christmas cheer or not, patrons will still launch Milk Duds at your head if you interrupt a Bing Crosby sing-along. Tickets are $10-$17 in advance or $10-$20 at the door, pending availability.
Music Box Theatre, 3733 North Southport Avenue (between Waveland Avenue and Grace Street); 773-871-6604.
Photo: Courtesy of Music Box Theatre.