Chicago’s Magnificent Mile Fills With Unique Family Fun This Festive Season

Discover family-friendly immersive experiences, cool eats and hot treats along Chicago’s Magnificent Mile. Use this handy list to get the memory making started for your family.

There’s no place that rivals the magic of the festive season more than Chicago’s Magnificent Mile with its millions of twinkling lights, hundreds of decorated trees, family-friendly fun and yummy treats — unless you count the North Pole, of course.

But even then, the folks behind making The Magnificent Mile so magnificent have pulled out all the stops this year as life returns to more normal to welcome families back again for fun day trips or even special weekend getaways made even more magical with festive themed hotel stays.

“We are all ready to celebrate together again, safely, and enjoy many of the holiday traditions that Chicago has to offer, including time spent with our families at our museums, visiting the nearby Christkindlmarket, ice skating at Maggie Daley Park, seeing world-class theater on Michigan Avenue, and checking out immersive experiences like The Dr. Seuss Experience or The Office Experience right here on The Magnificent Mile,” says Kimberly Bares, President and CEO of The Magnificent Mile Association.

Families will find more than 20 businesses that have created unique offerings especially with them in mind. Bares and her team took a few moments away from checking their list to share a few ideas to get you started on planning your next trip to The Magnificent Mile.

Dressed for the festive season

Chicago’s Magnificent Mile hotels simply love the holidays and festive season, judging by the creativity the staff at each of them pour into creating themed lobbies and room packages to excite the imagination. There’s a perfect destination for every family this holiday.

“The Magnificent Mile is a special place throughout the year but during the holiday season it becomes a truly magical destination. The district comes alive with twinkling lights and holiday décor and the sidewalks are filled with shoppers rushing along their way,” says Maria Zec, Regional Vice President and General Manager of The Peninsula Chicago.

“It’s like a Christmas card come to life.”

Take a self-guided visit to one of these spots and discover overnight fun and special family stay offers at

Winter ski lodge: You don’t need to hop a plane to experience the feel of a winter ski lodge. Head to The Fairmont Chicago, Millennium Park. Through February, it has transformed its lounge into a winter lodge with cozy decor, indoor fire pits, fun family programming and even overnight packages for families. A must-try is Chef William Schultz’s wintery-themed bites like Sweet and Savory Fondue and Oh So Delish Hot Chocolate served in a lodge-themed collector cup.

“The goal is to help guests ‘Experience the Grandest of Feelings’ in a Chicago winter setting. We wanted to bring a new meaning to staycationing for this season. More than ever, people are looking for unique ways to come together, relax, recharge and have fun. … There is no better way to celebrate winter than in a warm and cozy lodge,” says Anita Rahman, Director of Sales and Marketing at Fairmont Chicago, Millennium Park.

Photo Credit: Swissotel’s Santa Suite

Santa’s Chicago home: Create a new holiday tradition with a private experience at the Swissotel’s Santa Suite, Santa’s swanky home-away-from-home where he can review the naughty and nice list without being bothered by the Elves (or Mrs. Claus!). Gather up 15 friends to visit the Big Man privately while sipping unlimited cocoa, champagne and holiday treats, plus cookie decorating, crafts, face painting and letter writing with a visit to Santa’s Post Office. You’ll even be doing good, with $50 from the visit donated to SOS Children’s Villages Illinois. You can extend the fun with an overnight stay the kids will truly never forget. A Hanukkah dinner package is also available.

Gingerbread Express: Take a ride in a special elevator at Trump Hotel Chicago through Dec. 25. The Gingerbread Express is decked out in more than 1,200 gingerbread bricks, candy canes and sweet treats for a holiday music-filled ride up to the hotel’s restaurant, Terrace 16.

Gobble up sweet eats

An Afternoon Tea has become a beloved holiday tradition for many Chicagoland families. Families will find several great options this year.

The Peninsula Hotel: Few spots offer one as special and elegant as The Peninsula Hotel, which not only hosts an amazing tea beneath its 20-foot tree but cherished time together. Families particularly look forward to the specially created Stories from the Tree. This year’s story, the fourth and final tale in the series, features the Reindeer as the main character, who journeys around the world to see (and taste) different Christmas traditions.

Not only is a portion of every tea served going to help The Chicago Public Library Foundation, The Peninsula is also hosting a book fair where visitors can bring in a new or gently used children’s book to donate to the library, Zec says.

“The last two years have been hard on all of us, and we have missed our guests and the opportunity to celebrate the holidays with them. This year, we are putting on quite the holiday show!” she says.

Photo Credit: The Peninsula Hotel

Four Seasons Hotel Chicago: Another unmatched holiday afternoon tea to experience is at the Four Seasons Hotel. Served in the Social Lounge, its winter wonderland-inspired tea features delightful savory treats, including classic cucumber sandwiches, quiche Florentine​ and turkey bites from Executive Chef Tristan Baker and whimsical sweets such as cherry Christmas tree cakes, snowflake vanilla choux profiterole​ and winter spice scones created by Pastry Chef Juan Gutierrez.

The Langham Chicago: The Langham’s historic Holiday Afternoon Tea hits all of the senses, from seasonally-themed desserts meant to make your family squeal with delight, such as Chocolate Ornament, Egg Nog Choux, Snowball Apple and Santa Belly Macron, to seasonal music around the beautiful tree to its sparkling yuletide décor, all created to bring families joy.

Harry Caray’s: For a quicker treat to warm up while out shopping, stop into Harry Caray’s 7th Inning Stretch along the Mag Mile for Italian hot chocolate. Sports fans, of course, won’t want to miss a chance to check out its Chicago Sports Museum, too. Plus, Harry Caray’s goes all out on decorations. This year at its River North spot, it is offering a special holiday edition of Nitti’s Supper Club that includes dinner and a show filled with laughs, gangsters, audience interaction and toe-tapping musical production, says Joanna DePorter, Vice President of Harry Caray’s Restaurant Group. At Navy Pier, it just opened its lakeside curling rink and is hosting a free holiday concert by American Idol finalist Manny Torres Dec. 23.

Fun abounds on Chicago’s Magnificent Mile

Sure, there are plenty of places to ice skate, including several great iconic spots on The Mag Mile itself, but why stay street level when you can go sky high? Skate above Michigan Avenue at The Peninsula Sky Rink. This hybrid rink is tucked into a winter wonderland with festive music and snowflake lighting. Plus, fill bellies with hot chocolate or cider and yummy treats. All money collected is donated to Ann & Robert H. Lurie Children’s Hospital of Chicago and Hephzibah Children’s Association. You can’t beat the price: $10 for kids, $20 for adults including skates.

Photo Credit: The Peninsula Hotel

Families will love visiting The Dr. Seuss Experience in Water Tower Place. This imaginative and interactive immersion into the wondrous world of Dr. Seuss offers nine different spots to try. Think swinging among Truffula Trees from The Lorax, getting lost in a brilliant balloon-filled maze from Oh, the Places You’ll Go!, strolling through colorful clovers listening for a Who from Horton Hears a Who!, or joining the Circus McGurkus!

Families with older kids who have discovered The Office on reruns (or for a parent date out) will find another immersive experience to explore as The Office Experience celebrates the TV show. Visitors can step inside the regional paper company, explore set recreations like the Dunder Mifflin Scranton Offices and Schrute Farms, get a closer look at original show props, and shop at The Office Experience Store for a little holiday gifting.

Where to park

Parking can be a worry for families. Yes, it’s completely normal to want easy — and affordable — parking when driving from the suburbs, but don’t worry this year. That’s covered, too, thanks to SP+ and SpotHero. Use or the SpotHero app to save on parking and to find the most convenient locations, hassle-free.

“We are truly the ideal holiday experience, from world-class hotels ready to welcome you for overnight stays with the entire family, to fun and festive holiday teas, specialty drinks, and seasonal dining experiences at our numerous restaurants. You’ll want to shop for everyone on your list at our retailers, including new openings at The Shops at North Bridge, and pop-up experiences located near Water Tower Place,” Bares says.

“There is something for everyone here.”

Content sponsored by The Magnificent Mile. Find even more family fun at

Chicago Parent Editorial Team
Chicago Parent Editorial Team
Since 1984, the Chicago Parent editorial team is trained to be the go-to source for Chicagoland families, offering a rich blend of expert advice, compelling stories, and the top local activities for kids. Renowned for their award-winning content, the team of editors and writers are dedicated to enriching family life by connecting parents with the finest resources and experiences our community has to offer.


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