Shivering on a Chicago Blue Line elevated train platform, I tug my parka tighter around me. My son and our family friends are at the Forest Park station to see Santa aboard a decorated train pulling his giant sleigh (atop an open-air flatbed car). Today the festive train starts here before heading into the Loop, its skyscraper skyline shrouded by lake-effect snow.
For more than 20 years, Santa has ridden the Chicago Transit Authority’s Holiday Train. On select weekdays and all weekends in December, Santa dashes through the Windy City on eight train lines, making scheduled station stops to pose for free photos, and, on some days, drop off food baskets to charitable groups. Jolly conductors dressed as elves volunteer to work the Santa shifts, handing out candy canes and taking family photos. You can go for a ride (for the standard $2.25) or just take a free peek inside the peppermint-and-cinnamon-scented passenger coaches decked out with twinkling lights, garland, big bows and Christmas-patterned upholstered seats. Holiday tunes play over the train’s speakers.
“All aboard the Santa Express!” the elf conductor announces before the train departs the station. The boys wave good-bye to Santa until the twinkling train disappears around the curve. “I ho-ho-hope you have your long underwear, Santa!” they shout. The conductor smiles. “Don’t worry, kids. Santa knows how to dress for Chicago winters,” he says.
Imagine that. How many times have I asked my son, “Do you have your hat and gloves?” I never thought my constant reminders about dressing for the weather sank in—until now. And knowing that my son is listening might in fact be the best Christmas gift ever.
Want to go? Check out the CTA Holiday Train schedule and track Santa’s rail travel: (312) 836-7000; transitchicago.com 
See a short video  of Chicago holiday fun, including the CTA Holiday Train.
(Photos courtesy of Chicago Transit Authority.)
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