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Your 24-hour holiday itinerary in the Loop

Posted  18 months ago

5 MIN READ – If you’re a traveler who only has 24 hours to spend in the Loop, or if you just want to plan the most amazing day packed with holiday celebration, you’re in luck: We’ve created this holiday itinerary that will guide you through a variety of options and all the best downtown spots to celebrate the season. With 24 hours to enjoy the holidays in the Loop, there is plenty to do all day and night.


Fuel up

You’ve got a long day of holiday fun ahead of you, so start it off with a quick, healthy breakfast. 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. 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!


Sugar Bliss

After all that shopping and sight-seeing, you might need a little pick-me-up. For a festive treat, stop by Sugar Bliss. You can’t miss out on their seasonal sweets, such as themed royal icing cookies, cupcake and cookie decorating kits, hot chocolate bombs, s’mores kits, macarons, and cupcakes. See which cupcake and macaron flavors are in rotation here


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! There are a ton of great spots to eat lunch in the Loop, and you can find your options here.


Holiday theatre in the Loop

Performing arts venues were unable to open during the 2020 holiday season, but theatre is back and better than ever this year! Check out Disney’s Frozen at the Cadillac Palace 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, Leslie Odom, Jr. - The Christmas Tour at CIBC Theatre, A&A Ballet’s The Art Deco Nutcracker at the Athenaeum Theater, The Joffrey Ballet’s The Nutcracker at Lyric Opera House, Sarah Brightman’s A Christmas Symphony at the Auditorium Theatre, Merry, Merry Chicago! with the Chicago Symphony Orchestra, and much, much more. 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. 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.


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.