Upcoming Events

Upcoming Events at Pioneer Court


Wintrust Magnificent Mile Lights Festival

Saturday, November 22

11AM – 7PM 

America’s Holiday Season Begins Here! From 11:00am to 4:00pm, families can enjoy a day full of festive fun at Lights Festival Lane in Pioneer Court. Highlights include free activities like Wintrust Photos with Santa, cheesecake decorating with Eli’s Cheesecake, live performances, and more! The 2025 parade down the Magnificent Mile will feature Grand Marshals Mickey Mouse and Minnie Mouse of Walt Disney World® Resort, fabulous floats with beloved friends from Walt Disney World® Resort, marching bands from across the country, musical celebrities, Santa Claus, The Wintrust Fireworks Spectacular, and one million lights illuminating The Magnificent Mile’s 200+ trees.

Holidays Start Here

Passport to Santa

Saturday, November 29 – Wednesday, December 31

Step into the North Pole with Passport to Santa, an interactive holiday adventure where every child becomes a traveler on a festive quest! Along the way, they’ll toss snowballs with Frosty, train with Rudolph, decorate cookies in Mrs. Claus’ Kitchen, strike toy soldier poses in Nutcracker Kingdom, write wishes with the Christmas Angel, and build sweet creations in Gingerbread Grounds. Each completed activity earns a stamp in their passport, which can be redeemed at Santa’s Workshop for prizes and a personal visit with Santa himself. Join the waitlist today for Passport to Santa in Chicago!

Come Aboard

Santa's Secret

Friday, November 28 – Wednesday, December 31

Get on Santa’s Naughty List – Slip through seven of Santa’s secret immersive holiday installations to find his hidden speakeasy—then toast the season with festive cocktails, delicious dining, Santa’s live band, and a jaw-dropping variety show including ballet, burlesque, aerial acts and more as Santa’s secrets are revealed…Shhh… don’t tell Mrs. Claus.

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