MORNING
Fuel up
Start the day with a brisk walk to Beatrix for a hand-crafted coffee drink made with Beatrix Coffee Roasters and a house-made pastry, with favorites including the Honey Cinnamon Latte, Hazelnut Oat Mocha, Lemon Blueberry Muffin, Banana Bread and more. Pop back in between holiday festivities for happy hour every Monday-Friday from 3-6 P.M. to sip on $5 local beers, $6 select wines, $7 hand-crafted cocktails and more.
Swing by Goddess and the Baker for pastries, acai bowls, breakfast sandwiches, and more, or try the cafe at Venteux for Parisian cafe fare with a contemporary twist. To try out what many say is the best breakfast sandwich in the Loop, stop in at Hero Coffee Bar. Find more Loop cafes and bakeries here.
Shop and see the sights
Downtown gets crowded fast during the holidays, so set aside some time in the morning for the chillest sightseeing experience. Have a free, fun experience for the whole family at Mindworks. Learn all about the science of human behavior, including the science of gift giving, gratitude, goal-setting, and much more. Plus, earn stocking stuffers like beanies, scarves, and books by participating in research studies.
Stop by The Art Institute of Chicago to snap a selfie with the wreathed lion statues by the museum steps. Walk past Macy’s on State Street to enjoy the traditional holiday window displays. While you’re at it, head into the store—and all the great State Street retailers—to knock out your holiday shopping before the crowds really hit!
AFTERNOON
Christkindlmarket
One of the most iconic downtown Chicago traditions of all is back this year after going virtual in 2020: Christkindlmarket. Inspired by the 16th century Christkindlesmarkt in Nuremberg, Germany, one of the first outdoor markets of its kind, the Christkindlmarket is well-known for its vendors’ high quality gifts and food, holiday cheer, and for being the ideal place for families to make unique memories.
Ice skating
There are two fantastic outdoor ice skating locations in the Loop, offering a little something for everyone. The Maggie Daley Park Ice Skating Ribbon is a quarter-mile ribbon that offers incredible views of the city and an atmosphere of good old-fashioned fun for all ages. The ribbon is not a traditional oval rink, but rather a track that winds and slopes, offering a one-of-a-kind ice skating experience. The McCormick Tribune Ice Rink, celebrating its 20th season, is a more traditional rink but also offers incredible skyline views. Nestled below Cloud Gate (“The Bean”), this is a picturesque experience you don’t want to miss.
Stop for lunch
Swing by The Walnut Room in Macy’s to dine under the Great Tree, or stop in at The Berghoff and you may just catch a glimpse of Santa! Whether you're a kid (or just remained one at heart), spotting Santa in the Loop is always a merry surprise.
There are a ton of great spots to eat lunch in the Loop, and you can find your options here.
EVENING
Holiday theatre in the Loop
The Loop's Theatre District is overflowing with amazing shows this holiday season. Ballet 5:8's Beyond the Nutcracker is coming to Chicago! Join this magical trip around the world to discover the true beauty of Christmas. Performances begin November 17 with Christkindlmarket performances in Daley Plaza. For all the young ballerinas, Museum 21C Chicago will be hosting Beyond the Nutcracker Books and Ballerinas on November 18. The full production goes onstage November 25 and 26 at the Athenaeum Theater in Chicago and continues December 16 and 17 at Lincoln Way East in Frankfort, IL. More information and tickets at Ballet58.org
Check out Boop! The Musical at CIBC Theatre, A Christmas Carol at Goodman Theatre, Home Alone in Concert with the Chicago Symphony Orchestra, ‘Twas the Night Before… by Cirque du Soleil at the Chicago Theatre, The Joffrey Ballet’s The Nutcracker at Lyric Opera House, Purchase theatre tickets from Hot Tix in advance to see holiday theatre at the best rates. Tickets are available at half-price at HotTix.org, or you can stop by their two Loop locations, 108 N. State at Guest Services inside of Block 37 or 72 E. Randolph.
Art on theMART
Don’t miss this larger-than-life experience: an artistic interpretation of The Joffrey Ballet’s The Nutcracker projected onto the Merchandise Mart’s 2.5-acre river-facade. Art on theMART is the largest permanent digital art projection in the world, right here along the iconic Chicago River. The projection can be viewed for free nightly at 7 and 7:30 p.m.
All of the lights
The Chicago Loop is always a lit-up wonderland, but especially so during the holidays. Feel the magic of the merry season as you stroll along the State Street holiday lights.
Head over to Millennium Park to witness the City of Chicago’s 108th Christmas Tree, or head north of the Loop to the Magnificent Mile for their annual Lights Festival.
STAY THE NIGHT
The Blackstone Hotel
This holiday season, create a new tradition with your loved ones and join The Blackstone Hotel for an unforgettable Presidential experience with this immersive luxury package. Complete with historical accents that transport you to the captivating 1960’s Kennedy Christmas, The Blackstone’s "A Kennedy Christmas" package welcomes families and travelers to indulge in a magically timeless holiday scene. Their famous Presidential Suite will become an immersive ode to the lavish 1960s Kennedy White House, embellished with a twinkling tree, marching nutcrackers and presidential details such as a letter typing station and cozy White House blanket.
The Palmer House Hilton
The Palmer House Hilton has been hosting visitors to the Chicago Loop for 150 years. It is America’s longest-operating hotel and offers guests the ultimate experience in luxury from the moment they arrive, with a two-story, gilded lobby with a formal staircase, marble-topped tables, velvet seating, and a ceiling mural depicting Greek mythology. It’s a Loop icon, and a wonderful place to end your long day celebrating the holidays in the Loop.
Kimpton Gray
In the center of the Chicago Loop, the Kimpton Gray is located close to several holiday festivities and winter activities. Between Vol. 39 and Boleo, there’s nowhere better to enjoy a nightcap and then head to bed.
theWit Hotel
Boldly living in the heart of Chicago’s theater, arts, and shopping district, theWit Hotel is the perfect spot to end your 24-hour holiday extravaganza. Stop by the 27th floor to enjoy one last drink or snack at ROOF on theWit, with unbeatable views of festive State Street, and then head up to your hip, modern room designed to celebrate creativity and expression.
See other Loop hotel options here.
