Christmas In Chicago: Visit The Windy City For Holiday Cheer

Chicago is captivating anytime of year with its stunning architecture and art installations, but it truly shines during the holiday season with twinkling lights and a calendar full of festivities making the city extra joyful. Sneak away to the Windy City during the holiday season for some holly jolly good fun, festive fare and all-around Chitown Christmas cheer in all its neighbourhoods. —Karen Kwan

Stay

Located in a restored historic landmark, the Chicago Athletic Association is in the heart of downtown Chicago, just steps away from Cloud Gate (where there are choir sing-alongs during the holiday season) and the Chicago Christmas Tree in Millennium Park (this year’s tree is an impressive 53-feet and eight-inch tall Colorado blue spruce). Inside the hotel, the lobby, which has a bit of a Hogwarts aesthetic, is warm and cozy with a fireplace and Christmas tree and gets filled with locals and guests working remotely in the space, and the Games Room gets packed with revelers enjoying cocktails and games, such as shuffleboard. The rooms are blissfully peaceful, though, with beyond comfortable beds and sporty decor (think pommel horses used as end-of-bed benches), a nod to the space’s origins as an 1890’s private club and fitness facility.

See

The city has already held its annual Wintrust Magnificent Mile Lights Festival to kick off the season, dazzling more than a million people, but Chicago truly dazzles all season long. There’s the Chicago Tree in Millennium Park (be sure to check out the skating rink, too–or rent some skates yourself and hit the ice); a pretty tree decked out with white lights and red bow at the Wrigley Building; the massive Merchandise Mart gets lit up in red and green; plus loads of shops and streets in the Loop are decked out with holiday finery. Soak up the pretty scenery after sunset by going on a stroll or take in the views from way above the city from Skydeck Chicago, 360 Chicago or step it up a notch and book a private helicopter tour with Vertiport Chicago to soar above the skyscrapers. (Tip: If you’re planning to visit several of Chicago’s landmark sights, consider getting the CityPass to save a bit on admission.)

Shop

From the 42 trumpets dressing up the exterior of Macy’s along State St. to all of the festive shop windows–like the adorable teddy bear at Ralph Lauren–just window shopping in the Magnificent Mile neighbourhood is fun in itself. But there’s plenty of great retail therapy to be had–for yourself or everyone on your list–from luxury goods at Burberry and Giorgio Armani to deals at Marshalls and Nordstrom Rack, and of course, great local shops such as Mary Mary (where you’re sure to find something for that hard-to-shop-for friend) and Maria Pinto (a Chicago fashion designer who’s done looks for Oprah Winfrey and Michelle Obama). For Christmas decor, stop into Chriskindl Market to shop the charming cabin-style booths for beautiful pieces, including handcrafted wooden pieces and glass ornaments from Eastern Europe. While you’re there, snap up a hot cocoa in a souvenir mug, and enjoy some winter comfort-food fare such as raclette, currywurst, potato pancakes and goulash soup.

Savour

The dark woods and cozy interior of the recently opened Chicago outpost of UK-favourite Hawksmoor makes it an ideal spot to grab dinner on a cold Chicago night. The steaks (all grass-fed, pasture-raised cattle) are cooked to perfection over charcoal and you can make it extra decadent with bone-marrow gravy and a serving of three bone-marrow oysters on the side. Be sure to save room for a rich, moist bowl of sticky toffee pudding to round out your meal. Foodies and fans of The Bear, take advantage of being in Chicago to tour some of the spots where the TV show was filmed with Chicago Food Tours. Yes Chef!: A Bear-Inspired Food Tourwill take you by bus to try foods and bevvies at several key spots you’ll remember from the show’s storylines–including where Sydney tries to hire staff in a back alley and Roeser’s Bakery, Chicago’s oldest family-owned bakery, where Marcus peers into the window in Season 1.

Sip

For fantastic views of the city, head to Cindy’s Rooftop at the Chicago Athletic Association, where you’ll find fire pits on the patio to keep you warm as you take in the skyline, or for an extra dose of yuletide cheer, head to Happy’s Holiday Bar; this pop-up bar transforms the Tank space on the street level of the hotel with twinkling lights and tons of decorations–including a toy train around the perimeter of the space–and serves up cocktails and bar snacks during the holiday season. For more extra festive vibes you want, head to Wrigleyville, where many of the neighbourhood’s bars and restaurants have been dolled up as a North Pole wonderland. For one, Stretch Bar & Grill turns into Elf’d Up–decked out with faux-snow and 1,000 decorative elves and ornaments, along with a menu inspired by the Christmas classic movie Elf (including Buddy’s breakfast pasta–a pile of spaghetti topped with maple syrup, chocolate fudge, syrup, marshmallow and a pop tart) and festive cocktails such as the Elfie Margarita.

Photos: Choose Chicago