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

Read on for featured holiday highlights. Head back to The Festive Season on The Magnificent Mile landing page for more great ideas, and be sure to visit our Shopping, Dining and Events Calendar to see what else is happening around The Magnificent Mile district through the new year! 

  • Curling by the Lake

    Harry Caray's is proud to feature the only lakefront Curling Rink in Chicago. Groups of up to 6 may reserve our rink for 45 minutes for $5 per person. Warming Huts can be added to the reservation for a $100 deposit (which will be applied to the food and beverage bill) to keep everyone warm while dining and drinking between turns. Curling Cocktails featuring Glenmorangie X are served in large format heated thermos for the entire group to share. Reservations are available every day on the hour from noon until close.

    Book your reservation!

  • Skating at The Sky Rink

    The Peninsula Chicago opens their Sky Rink for its ninth 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

    Saturday, November 20 through Saturday, December 25, 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 and the students of the Culinary Arts Program (C-CAP) which is a nonprofit that provides culinary, job and life skills to over 20,000 middle-and-high school students in seven regions across the United States.

    Guests who ride the Gingerbread Express will be greeted by the sweet aromas of the season, celebratory holiday music and more than 1,200 gingerbread bricks made in-house.  It’s the most joyful ride of the season!

  • Holiday Afternoon Tea

    At Four Seasons Hotel Chicago, experience the ultimate joyful afternoon treat, perfect after a busy day of holiday shopping or as a special get–together of family and friends. Served in the Social Lounge, a vibrant art and gathering haven, the winter wonderland-inspired tea features delightful savoury treats including classic cucumber sandwiches, quiche Florentine​ and turkey bites from Executive Chef Tristan Baker and whimsical sweets courtesy of Pastry Chef Juan Gutierrez such as cherry Christmas tree cakes, snowflake vanilla choux profiterole​ and winter spice scones. Steeped in the art of the draw, tea service boasts more than twenty-five of the finest varietals from Chicago-based tea aficionados Rare Tea Cellar.

    Learn More

  • 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 26 to January 9, 2022, daily with seatings at 2:30 p.m. and 4:30 p.m.

    Learn More

  • Caroling at The Driehaus Museum

    Stop by The Driehaus Museum for caroling, roasted chestnuts, and holiday cheer on Saturday, December 18 from 3:00 - 6:00 p.m.

  • Celebrate the holidays at the Chicago Architecture Center!

    Oh what fun it is to discover Chicago's rich architecture with Chicago Architecture Center this Festive Season! Buy one adult admission ticket to the Chicago Architecture Center and get one ticket free with promo code NEIGHBOR this holiday season! Explore awe-inspiring exhibits on skyscrapers and the international race to build supertall, plus a large-scale interactive model of Chicago with over 4,200 buildings. Don’t forget to visit the reimagined CAC store to stock up on gifts for everyone in the family.

    Offer valid on full price adult tickets. Valid November 20, 2021 through December 31, 2021. Must be redeemed in person at the CAC Box Office. Not redeemable on CAC virtual programs, walking tours, or river cruises. Subject to availability. Not redeemable in whole or part for cash.

    Buy Your Tickets


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