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The Windy City isn’t just bluster. You can find adventure, romance and relaxation—you just need to know where to look.
Chicago Shakespeare Theatre
Laugh, cry and satisfy your dramatic side with a performance by this Tony Award-winning theater. From plays, to musicals to family-friendly performances—totaling nearly 20 productions throughout the year—you’ll have no problem finding a show that fits your mood or challenges you to think outside the box.
The Museum of Contemporary Art Chicago
The MCA Chicago’s mission is to showcase the provocative side of contemporary art. And that they do. Slip into the intriguing space and meander through exhibitions with disparate themes such as “how the internet has changed the way we experience the world” or how two artists “play with balance and gravity to make compelling sculptural statements.”
Hotel Julian Chicago
Ready for an original remix? Hotel Julian crafts an experience that’s equally charming for its roots in history and art, and exciting for its take on modern luxury. Located on Michigan Avenue just a quick walk away from Millennium Park—outfitted with a state-of-the-art gym and gastro steak bar—this boutique hotel is a chic home base for an artful adventure.
Score some tickets and make your way to the United Center for same fast-paced, edge-of-your-seat entertainment. The six-time Stanley Cup champions (and their die-hard fans) guarantee a show like no other on tap in the Windy City.
Sometimes the best way to explore a city is on two wheels. Rent a Divvy bicycle (there are hundreds of locations to do so throughout the city) and ride the Lakefront Trail. You’ll be rewarded with immaculate views of the skyline, fresh air and 18-miles of buttery-smooth, car-free cruising.
Skating Ribbon at Maggie Daley Park
Not a rink. Not an oval. Not quite what they’ll be expecting when you ask if anyone’s up to hit the ice. The winding quarter-mile ice-skating ribbon twists through Maggie Daley Park beneath the Chicago skyline and is complete with hot chocolate pit stops. The unique twist on a wintertime staple usually opens mid-November and remains open until mid-March. Skate rentals are available.
The Magnificent Mile
Before you indulge in retail therapy, traverse the stunning skyscraper canyon of Michigan Avenue and soak up its international allure. You’ll hear languages from around the world before you embark on some of the best shopping on the planet. With over 460 retailers, you’ll find all the luxe labels, popular brands and impressive department stores your closet craves.
Thrift dreams come true in Wicker Park. Head to North Milwaukee Avenue and get lost in the street’s bounty of beautiful vintage. Una Mae’s is a Chicago staple; Buffalo Exchange offers affordable finds; Vintage Underground makes it easy to find stunning jewelry and accessories. Refuel with a little coffee at the Wormhole (Yes. That’s a Back to the Future DeLorean inside the shop) and keep hunting at the other shops dotting the street.
There’s no better way to get into the holiday spirit. Bundle up and head to the open-air Christkindlmarket in Chicago’s Loop for an evening of hot chocolate, glühwein and glitzy ornaments galore. The inviting holiday village has become a Chicago wintertime tradition and just the right place to find some fun gifts and get your holiday fix.
Waldorf Astoria Chicago
Get glitzy and go full-on glam with a stay at this iconic Gold Coast hotel. From the world-class service to the award-winning spa, the Waldorf is all about luxury. Rejuvenate with a massage or, if it’s chilly outside, enjoy the roar of your very own in-room fireplace.
The Viceroy Chicago
What do meditation tips, a 30-foot tall poem wall, and a roof-top pool have in common? They’re all just a few of the laid-back luxuries at The Viceroy Chicago in the Gold Coast neighborhood. The hotel features chic accommodations, a restaurant led by a Michelin-starred chef, and even weekly yoga classes (open to the public Saturday mornings).
There’s something about a brewery on a frosty day. New flavors. Warm company. Lively beerhalls. Abundant samples. Start with local favorites like Off Color Brewing and Goose Island Brewery, enjoy a flight or two, and plan your next stop.
Chicago Children’s Museum
A quiet, musty museum visit this is not. Maritime make-believe will be a breeze with the three-story schooner (be sure to climb to the crow’s nest), and the kids can be the archaeologists they’ve always dreamed while they dig for dinosaur bones.
Centennial Wheel at Navy Pier
Looking for panoramic views of the lake and city? Take a ride on one of the skyline’s most exciting features. The Centennial Wheel at Navy Pier is almost 200-feet tall, and its enclosed gondola carts make the thrill comfortable no matter the season.
Who said you can’t appreciate a dolphin’s acrobatic antics in the heart of the Midwest? The Shedd Aquarium is one of just three aquariums in the U.S. home to these flippered friends, and so many more. The kids won’t believe how big the beluga whales are in the Abbott Oceanarium and might just beg you to bring home a sea otter. (Don’t worry. Consolation stuffed animals are available in the gift shop.)