Chicago Kicks Off the Holiday Season With The Wintrust Magnificent Mile Lights Festival Nov. 19

Chicago will officially flip the switch on the holiday season this weekend during the Wintrust Magnificent Mile Lights Festival, kicking off the most wonderful time of the year in the Windy City. A 31-year tradition, the weekend-long holiday celebration includes family-friendly, free festivities from a ceremonial tree lighting to America’s third-largest parade, grand marshaled by Mickey Mouse and Minnie Mouse from the Walt Disney World Resort, and a spectacular fireworks finale. 

Photo by Brooke McDonald

Wintrust joins the festival this year as the new title sponsor; AT&T and Enjoy Illinois are presenting sponsors. 

“More than 30 years ago, we formed Wintrust as a community bank and it is fitting that we join The Magnificent Mile Association and district businesses to bring this thrilling and timeless holiday tradition to the many families who live in and travel to Chicago to start their own holiday celebrations together each year,” says Edward J. Wehmer, Wintrust Founder and CEO.

Known as “Chicago’s Community Bank” and voted Best of 2022 – “Best Bank” by Better readers year after year, Wintrust is the perfect partner for the iconic Chicago festival, says Wendy Schenker, Wintrust Vice President of Marketing and Chief Entertainment Officer.

Wendy Schenker, Wintrust Vice President of Marketing and Chief Entertainment Officer

“We’re Chicago’s bank, this is an iconic Chicago event — what a perfect partnership,” Schenker says. “They’ve been doing this for 31 years, we’re in our 31st year. Everything seemed to line up.”

On Saturday, Nov. 19, between 11am and 4pm, Lights Festival Lane hosts a variety of family-friendly activities including photos with Santa courtesy of Wintrust, special appearances by Enjoy Illinois’ Big Lincoln, and free cheesecake from Eli’s Cheesecake Company

“We love the fact that this is a community event that’s free and everyone can come down and enjoy it at no cost,” says Schenker noting other can’t-miss moments courtesy of Wintrust. “We’re excited to have the Pointer Sisters on our float. We’re going to be sponsoring the Crystal Lake Strikers. We’re going to have a bunch of our mascots from our partners around the city dancing in the parade. The fireworks spectacular at the end will be a real showstopper and we’re just really excited to be a part of all of this.”

The Wintrust Magnificent Mile Festival Parade

Kicking off at 5:30pm Nov. 19, Grand Marshals Mickey Mouse and Minnie Mouse from Walt Disney World Resort will lead the parade along The Magnificent Mile between Oak Street and Wacker Drive.  

Photo by Brooke McDonald

Raevon Redding, one of Walt Disney World’s 2022-2023 Ambassadors, also traveled to Chicago from Orlando to join Mickey and Minnie in representing the Most Magical Place on Earth.

“I have the honor of representing all 75,000 Cast Members that work at Walt Disney World Resort and we are thrilled to be here in Chicago because we make so much magic in Orlando that we just had to bring some of the magic here,” Redding says. “Mickey and Minnie love spreading the cheer and the holidays wherever they get the opportunity. This is their 27th year being here in Chicago, and they’ve brought some friends to help celebrate.”

Walt Disney World Ambassador Raevon Redding joins Mickey Mouse and Minnie Mouse. Photo by Brooke McDonald

Fans of Disney’s runaway hit film Encanto will be thrilled to see Mirabel traveling along the parade route in a horse and carriage. Goofy and Pluto will also keep it holly and jolly, representing EPCOT, and Chip and Dale will be on hand to help commemorate Disney World’s 50th Anniversary.

The parade will feature impressive floats, balloons and, in addition to The Pointer Sisters, more star-studded musical acts including The Spinners, Debbie Gibson, C&C Music Factory and cast from Broadway In Chicago’s The Lion King and Wicked, as well as Lookingglass Theatre’s The Steadfast Tin Soldier. 

The evening’s final two finale moments both come courtesy of Wintrust as well. Santa Claus will helm the grand finale float, presented by Wintrust. Then, at 7pm, the Wintrust Fireworks Spectacular will blast off over the Chicago River. 

“We’re thrilled that we’re going to be the title sponsor for several years to come and this kicks off the holidays,” Schenker says. “This brings economic growth to the city, which we’re happy for. The hotels are full, the restaurants are booked and we’re really happy to be a part of something so positive for the city.”

The Wintrust Magnificent Mile Lights Festival Schedule

Friday, Nov. 18: 4 p.m. – Tree lighting at The Wrigley Building (410 N. Michigan Ave.)

Saturday, Nov. 19: 11 a.m. – 4 p.m. – Lights Festival Lane (401 N. Michigan Ave.); 5:30 p.m. – The Wintrust Magnificent Mile Festival Parade Steps Off – (Oak St. & Michigan Ave. south to Wacker Dr.); 7 p.m. – The Wintrust Fireworks Spectacular (Chicago River and Wacker Dr.)

How To Watch From Home

ABC 7 Anchors Cheryl Burton and Alan Krashesky host this year’s festival, along with Hosea Sanders, who will cover the festivities at street level. The parade will air on ABC 7 Chicago on Sunday, November 20 at 6 p.m. CT, Saturday, Dec. 10 at 11 a.m. CT, and Christmas Eve at 4 p.m. CT. Additionally, The Wintrust Magnificent Mile Lights Festival® broadcast will air in 186 US markets throughout the holiday season, reaching nearly 100% of the country plus Toronto, Canada, with repeat airings in multiple markets.

The Lights Festival Parade will be available on demand and stream exclusively on and ABC 7’s Connected TV Apps. Find local broadcast times at or check local listings.

More from Better:

Brooke Geiger McDonald Better Disney

Brooke Geiger McDonald is the national content director for Make It Better Media Group. A Chicago native, she has worked for publications like O, The Oprah Magazine and SHAPE Magazine and her work has appeared in The Points Guy, Parents, TravelPulse, Attractions Magazine, MSN and more. Her favorite nonprofits to support include Give Kids the World Village and Shedd Aquarium. Follow her on Instagram @brookegmcdonald and Twitter @BrookeGMcDonald.


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