Holidays @ Skydeck Chicago!

What Holiday Events Are Happening at Skydeck Chicago in 2026?

This season brings Santa Photo Sessions, Santa on The Ledge, Holiday Pie in the Sky family lunches, The Skydeck Express (a holiday-decorated L train replica), live student performances, a giant gingerbread Chicago skyline, and a Holiday Market at Willis Tower, plus festive décor from The Chicago Museum to the 103rd floor.

• Holiday Décor & Photo Ops: November 13, 2026 to January 4, 2027
• Santa Photo Sessions at Skydeck: November 14 to December 24 (daily times)
• Santa on The Ledge: December 5 and 12, 10:00 a.m. to 1:00 p.m. (event details)
• Holiday Pie in the Sky Family Lunch: December 5 and 19, 12:00 p.m. seating (menu and pricing)
• Buddy the Elf Visits Skydeck: December 8, time to be announced
• Willis Tower Holiday Market: December 8 to 10, 11:00 a.m. to 2:00 p.m., plus an evening session on December 10 from 4:00 to 6:00 p.m. (market details)
• Merit School of Music String Student Performances: December 9 and 16, 10:00 a.m., in Catalog at Willis Tower
• Mitchell Elementary School Choir Performance: December 11, 10:30 a.m.
• Choose Chicago Dance on Broadway Performance: December 12, 3:30 p.m., on the 103rd floor
• Holiday Jam Pajama Promo: December 21 to 26. Visit in your favorite holiday pajamas and receive a complimentary 6×8 printed photo on The Ledge.
• Willis Tower Gingerbread Display: On display throughout Holidays @ Skydeck

Event dates and times are tentative and subject to change.

Step aboard The Skydeck Express and pose at festive photo ops throughout The Chicago Museum. In December, catch Merit School of Music string students performing in Catalog at Willis Tower, plus a Mitchell Elementary School choir performance. Then head up to the 103rd floor, where The Ledge puts you 1,353 feet above a city dressed for the season.

When Can You Get Santa Photos at Skydeck Chicago?

Santa Photo Sessions run daily from November 14 to December 24, with no sessions on Thanksgiving Day. Times shift throughout the season, so check your date before you go:

Santa may also make informal “Selfies with Santa” appearances during the season.

Can You Meet Santa on The Ledge at Willis Tower?

Yes. On Saturday, December 5 and Saturday, December 12, Santa will be on The Ledge from 10:00 a.m. to 1:00 p.m. Say hello and snap a photo with Santa in the glass boxes, 1,353 feet above Chicago, with the city as your backdrop.

What Is the Willis Tower Gingerbread Display?

Among this year’s planned holiday highlights is a large-scale gingerbread scene depicting the city, created in collaboration with Chicago chef and restaurateur Chris Teixeira and acclaimed cake artist and pastry chef Miko Kaw Hok Uy. The display is anticipated to be up November 13 – January 4.

The design will feature Chicago icons including the Wrigley Building, the Hancock Building, the Bean, a Ferris wheel, and bridges over the Chicago River, with lights, moving elements, and a snow effect. Most pieces will be made from edible bakery creations, with the two largest towers built by Willis Tower carpenters.

Why Visit Skydeck for Christmas in Chicago?

Skydeck gives you a holiday view of Chicago you can’t get anywhere else: up to 50 miles across four states from the highest observation deck in the United States, without the winter chill.

• Step out on The Ledge: Glass balconies extending 4.3 feet from Willis Tower, 1,353 feet above the city.
• Explore a festive Chicago Museum: Holiday photo ops, twinkling lights, and the decorated L train replica on your way up.
• Make it a celebration: Pair your visit with Pie in the Sky, Giordano’s Chicago-style pizza served 99 or 103 floors up.

Make it your family’s highest holiday tradition. Holidays @ Skydeck is a warm, indoor celebration high above the city, and there’s more to see at Willis Tower, from the giant gingerbread Chicago skyline to the Willis Tower Holiday Market, December 8 to 10.

Can You Have Lunch with Santa at Skydeck?

Yes. Holiday Pie in the Sky is a festive family lunch 103 floors above Chicago, with Santa stopping by every table to say hello and pose for photos. Seating is at 12:00 p.m. on Saturday, December 5 and Saturday, December 19.

• For the kids: A gingerbread decorating station and kid-friendly holiday movies on a 96-inch projector screen.
• Adult menu: The full Pie in the Sky menu of salad, pizza, and dessert.
• Kids’ menu: Chicken tenders or mac and cheese, a side, and dessert.
• Holiday dessert: Peppermint Cheesecake, made from scratch with crushed peppermint candies and a chocolate cookie crust, finished with a border of whipped cream.

Pricing: $149 per adult and $25 per child under 10. A child ticket is required for each child under 10, and space is limited.

When Is the Willis Tower Holiday Market?

The Willis Tower Holiday Market is scheduled for December 8 to 10, 2026, from 11:00 a.m. to 2:00 p.m. each day, with an added evening session on Thursday, December 10, from 4:00 to 6:00 p.m. It’s an easy add-on to a Skydeck visit for gifts and seasonal shopping.

What Can You Do at Skydeck Between Christmas and New Year’s?

Holiday décor and photo ops stay up through January 4, 2027, so the week after Christmas is still a great time to visit. Santa Photo Sessions end December 24, but the twinkling lights, holiday L train, and festive Chicago Museum remain, along with the views from the 103rd floor and The Ledge. Through December 26, guests who visit in their favorite holiday pajamas also receive a complimentary 6×8 printed photo.

Can Groups Perform at Skydeck During the Holidays?

Yes. Holiday performance opportunities are available for groups. Email sales@theskydeck.com to book your group’s holiday performance. Planning a visit instead? Learn about group tickets and visits.