Chicago Initiatives The Sky Rink Chalet

Festive Experiences

Explore The Magnificent Mile this winter for a multitude of festive experiences for the whole family! Put your skating abilities to the test at Chicago's only rooftop skating rink, fixate your eyes on the million twinkling lights that line Michigan Avenue, or find yourself nibbling on petite finger sandwiches and sipping traditional afternoon tea. This season, continue cherished traditions and create new ones on The Mile!


Featured for The Festive Season

Book your stay, enjoy world-class shopping, sweet treats, and great eats; now is the time to discover and delight, all season long. Let's get festive, together. 

  • Skating at The Sky Rink

    The Peninsula Chicago opens their Sky Rink for its tenth season this year! Tucked into a pine tree winter wonderland on The Terrace, the Sky Rink is surrounded by Chicago's skyscrapers and the million twinkling lights from Michigan Avenue. Festive music and snowflake lighting creates the perfect winter activity for the family. Pair your time skating with the rink's outdoor menu featuring a selection of hot beverages and snacks including hot chocolate, hot cider, treats, and more! 

    View the Sky Rink Calendar Dates

  • Gingerbread Express Elevator

    Starting on Friday, November 18, guests and visitors will be transported to a holiday wonderland in Trump Hotel Chicago’s Gingerbread Express. The property has designated one special elevator traveling up to the hotel’s signature restaurant, Terrace 16, that will be decked in everyone’s favorite holiday indulgences – gingerbread, candy canes and more sweet treats. 

    Envisioned by the hotel’s Executive Pastry Chef, Roberto Hernandez, guests who ride the Gingerbread Express will be greeted by the sweet aromas of the season, celebratory holiday music, and more than 1,300 gingerbread bricks made in-house. 100% of donations made will go to the children of St. Jude Children’s Research Hospital. It’s the most joyful ride of the season!

  • Light up The Lake

    Light up The Lake, Chicago's largest indoor winter wonderland returns this holiday season at Navy Pier! Experience the magic of the season by getting lost in interactive light displays, a skating rink, an illuminated Winter Wonderfest Forest, visits with Santa Claus, and much more. 

    Explore Light up The Lake
  • The Peninsula Chicago

    Festive Holiday Afternoon Tea

    Join The Peninsula Chicago this festive season for their traditional Festive Afternoon Tea. The favorite tradition shared by many families is served under their 20-foot Christmas tree accompanied by a variety of finger sandwiches and petite seasonal pastries. This spectacular holiday activity is the perfect outing for friends and family to get in the festive spirit. Festive Afternoon Tea is offered November 25 to January 8, 2022, daily with seatings at 2:30 p.m. and 4:30 p.m.

    Learn More
  • Lookingglass Theatre Company

    The Steadfast Tin Soldier

    Chicago's beloved holiday tradition returns to Lookingglass Theatre Company this holiday season, a classic the whole family will treasure! Based on Hans Christian Andersen's story about a little tin soldier who never gives up, Ensemble Member Mary Zimmerman's production is a gorgeous spectacle of music and movement that the Chicago Tribune calls " A treat for all ages! It's transformational, truly. Barely more than an hour-long, this is one holiday experience you don't want to miss.”

    Purchase Your Tickets

  • Broadway in Chicago

    Now Playing at Broadway in Chicago!

    Disney's The Lion King

    Giraffes strut. Birds swoop. Gazelles leap. The entire Serengeti comes to life as never before. And as the music soars, Pride Rock slowly emerges from the mist. This is Disney’s THE LION KING, making its triumphant return to Chicago!

    More than 100 million people around the world have experienced the awe-inspiring visual artistry, the unforgettable music, and the uniquely theatrical storytelling of this Broadway spectacular – one of the most breathtaking and beloved productions ever to grace the stage.

    Winner of six Tony Awards®, including Best Musical, THE LION KING brings together one of the most imaginative creative teams on Broadway. Tony Award®-winning director Julie Taymor brings to life a story filled with hope and adventure set against an amazing backdrop of stunning visuals. THE LION KING also features the extraordinary work of Tony Award®-winning choreographer Garth Fagan and some of Broadway’s most recognizable music, crafted by Tony Award®-winning artists Elton John and Tim Rice. There is simply nothing else like THE LION KING.

    Purchase Your Tickets

    Dear Evan Hansen

    A letter that was never meant to be seen, a lie that was never meant to be told, a life he never dreamed he could have. Evan Hansen is about to get the one thing he's always wanted: a chance to finally fit in. DEAR EVAN HANSEN is the deeply personal and profoundly contemporary musical about life and the way we live it. DEAR EVAN HANSEN has struck a remarkable chord with audiences and critics everywhere, including The Washington Post who says DEAR EVAN HANSEN is “Theatrical magic. One of the most remarkable shows in musical theatre history.” The New York Times calls it “a breathtaking knockout of a musical. "And NBC Nightly News declares the musical “an anthem resonating on Broadway and beyond." DEAR EVAN HANSEN features a book by Tony Award winner Steven Levenson, a score by Grammy®, Tony® and Academy Award® winners Benj Pasek and Justin Paul (La La Land, The Greatest Showman), and direction by four-time Tony Award nominee Michael Greif (Rent, Next to Normal).

    Purchase Your Tickets

    A Magical Cirque Christmas

    Use code MAGMILE to unlock $20 off a pair of tickets for A MAGICAL CIRQUE CHRISTMAS valid for December 6, 7(mat/eve), & 8 performances in front/rear balcony seating. The world's greatest entertainers unite for a spell-binding and incredible holiday production – A MAGICAL CIRQUE CHRISTMAS! Experience the enchantment of Christmas as Magical Hostess Lucy Darling takes you through an evening of dazzling performers and breathtaking cirque artists, accompanied by your favorite holiday music performed live. Get into the spirit of the season with this merry treat that's perfect for the entire family.

    Purchase Your Tickets

    The Twenty-Sided Tavern

    Use code MAGMILE to unlock $35 tickets for all Thursday and Sunday Evening performance of THE TWENTY-SIDED TAVERN through December 18. Embark on a journey that might involve dungeons, might involve dragons, and is guaranteed to be unlike anything you've ever experienced. Dive into this raucous comedic explosion full of riddles, puzzles, combat and more — the story’s in your hands and YOU must decide our heroes’ fate. Laugh along and choose between over thirty playable characters as they explore dozens of different rooms and race toward an incredible, one-of-a-kind ending based on your actions and decisions. At The Twenty-Sided Tavern, you are not merely an audience member; you are an adventurer ready to change the fate of the world around you, and the story will never be the same again.

    Purchase Your Tickets


    WICKED, the Broadway sensation, looks at what happened in the Land of Oz…but from a different angle. Long before Dorothy arrives, there is another young woman, born with emerald-green skin—smart, fiery, misunderstood, and possessing an extraordinary talent. When she meets a bubbly blonde who is exceptionally popular, their initial rivalry turns into the unlikeliest of friendships…until the world decides to call one “good,” and the other one “wicked.” From the first electrifying note to the final breathtaking moment, WICKED—the untold true story of the Witches of Oz—transfixes audiences with its wildly inventive story that USA Today cheers is “a complete triumph! An original musical that will make you laugh, cry, and think.”

    Purchase Your Tickets



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