Twinkling lights, cheerful music and a man in a red suit are rumbling along Chicago’s train tracks. It’s that time of year when the Chicago Transit Authority (CTA) holiday train and bus — officially known as the Allstate CTA holiday fleet — offer a sometimes unexpected dose of red and green joy.

Curious City listener Kristina Bittorf remembers her first ride on the holiday train. She was waiting for a Brown Line train after work. She says her mood instantly changed when the doors opened and out popped an elf to greet her with a candy cane.

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“We like to complain about the CTA,” Bittorf said. But when the holiday train or bus pulls up, “I’m like, ‘The CTA can do no harm.’”

Originally from the Philippines, Bittorf says her family celebrated Christmas heavily. So seeing how much the city holds the holiday train as a Christmas tradition was meaningful to her.

“It made me feel right at home, and it makes me really look forward to the holidays here in Chicago,” she said.

Bittorf has seen Santa Claus flying past on the tracks along the interstate, sometimes with rain and snow whipping around. Yet, he seems to always have a smile when he pulls into the L stations. It got Bittorf wondering about Santa, the elves and the history of the holiday train.

The CTA takes the holiday train and bus seriously. Planning starts as early as July, and assembly and mechanical work begin in September. In recent years, the CTA has been able to set aside six dedicated cars for the holiday train that are kept at a CTA shop in Skokie when they aren’t in use. But while the holiday train has become a big, glittery affair, the CTA’s longest-running holiday display started from humble beginnings.

‘Seasons Greetings from the CTA’

In 1992, rail maintenance workers on the Blue Line had an idea to deliver food to charities along the route. Jeannine Messina, senior manager of CTA’s infrastructure division, said they used an out-of-service O’Hare-bound train and put a sign out front that said “Seasons Greetings from the CTA.” The workers delivered about 50 food boxes that year.

“Employees would raise money, collect money throughout the year. And then around Christmas we would get together and purchase food, make boxes and give them back to the community,” she said.

The holiday train still makes those deliveries, but now it’s grown to more than 600 boxes delivered seasonally to charities like the Phoenix Outreach of Chicago and Nourishing Hope.

Messina said over the years more decorations were added to the train, including tinsel and lights brought in by CTA employees.

She said it wasn’t until 1996 that this decorated train started picking up passengers.

“We had the train decorated, and it would sit up on the overpass and people would see it on the expressway and we started getting inquiries about it,” Messina said. “That’s how it ended up turning into the holiday train that you see today where we pick up riders.”

The holiday train has had corporate sponsorships since 2015 to help cover the cost of decorating and running it each year.

But there were a couple of times when the train was in danger of coming to a halt.

Back in December 2004, with a budget deficit and pending layoffs, then-CTA President Frank Kruesi proposed cutting the holiday train.

News stories ran with headlines like “Santa gets the ax as CTA cancels holiday train.” It caused an uproar, both internally at the agency and among riders. Then-board member Sue Leonis was quoted in the Chicago Tribune saying, “Board members are pissed. [Staff] made a mistake, and they better find a way to fix it.”

CTA President Kruesi was labeled a Grinch. And a couple of days later, the CTA reversed course, announcing the holiday train was back on track.

The train was nearly diverted again in 2020, during the height of the COVID-19 pandemic. Officials questioned whether the CTA could in good conscience jam a bunch of people together when health officials were discouraging large gatherings at grandma’s house. In the end, the CTA went for it, but without passengers.

Messina remembers riding the empty holiday train and seeing people waving from afar.

“They would be down in their alleyways or in front of their house, and they’d be excited to see the train pass,” she said. “It really meant something to them that we still ran the train.”

Employees on the “nice list”

There are a lot of questions about the person riding Santa’s sleigh on the flatbed car. In the early days of the holiday train, before it actually started picking up passengers, “Santa” was a CTA employee dressed the part.

But today, CTA officials insist it is the real Santa Claus from the North Pole riding the train.

Santa stays outside on the flatbed car for each run. He doesn’t get to go inside between station visits.

“There are a lot of cross winds that can happen between the buildings and sometimes Santa can lose his hat,” Santa said. “But the elves that are very helpful always have a spare hat for me.”

He’s endured the rain, snow, wind — everything Chicago weather likes to throw in December.

Fortunately, a foot heater was added to the flatbed as well as a hand-warming bar behind the sleigh.

CTA officials say working as a CTA elf is a much sought-after role. Jeannine Messina says the elves are fully vetted.

“They can’t have anything naughty on their record at all,” she said.

While Santa and the elves might be great at their normal jobs, they get extra training for this special commute.

“So they can understand the ins and outs of our train and just to make sure they know how to welcome the customers aboard and they interact with them when they’re riding the train with us,” Messina said.

The holiday train has between 10-17 elves working at a time. They pass out about 150,000 candy canes over the course of the season and do a lot of crowd control. They make sure people are folding up strollers and moving down the aisles, and are responsible for turning people away once cars reach capacity.

Santa says he’s seen some risky behavior over the years, like people jumping on the flatbed car to give him a hug. The CTA discourages that — especially if the train is in motion and the emergency break needs to be engaged. The sudden stop can cause injury to other passengers. Santa warns people not to get pushy on the platforms.

“There are certain naughty parents who push in front of children to get a picture with Santa,” he said. “The key is to be nice, polite and wait your turn. The elves are there to remind people to do that, and sometimes CPD shows up to help.”

Amid long delays and a rail operator shortage, commuters and employees have legitimate gripes with the CTA. But Santa says the holiday train offers a bit of joy that’s hard for anyone to deny.

“There’s nothing like watching somebody kind of grumpy getting on the train and then leaving the train and waving and yelling, ‘Merry Christmas, Santa,’” he said. “It makes my heart full.”

More about our question-asker

Kristina Bittorf is the director of finance at a Chicago-based tech company. She lives in the North Center neighborhood with her husband and two young sons.

She says her first encounter with the CTA holiday train was by coincidence when she was waiting for the Brown Line train after work more than a decade ago.

“I was greeted with this magical, brightly lit train, and you can just hear the buzz from the platform as it was approaching,” she recalled. “They trick it out with all the lights. There are CTA employees that are dressed up waiting by the doorways to greet you and hand out candy canes. I was just transported.”

Kristina says she’s been a fan of the holiday train ever since, but she sees it through different eyes since having children. It’s become an annual tradition to check the holiday train schedule for a chance to catch a ride and snap a photo with Santa.

Susie An is Curious City’s editor. Follow her @soosieon.