The Chicago Transit Authority’s holiday El—a train bedecked with decorations, cinnamon fragrance piped through the air vents and a flatbed in the middle carrying a sleigh-bound Santa for the ride—took its inaugural trip in 1992. It started with a simple “Season’s Greetings from the CTA” sign on the front of an out-of-service train that delivered food to reps from various charities, who would meet it on designated platforms. It started carrying passengers in 1996, and has grown in popularity since to become a beloved city tradition.
The holiday El runs on each of the CTA’s eight train lines. For a complete schedule, go to 008000, but we suggest taking it along the newly improved Green Line from downtown to the westernmost stop at Harlem, then returning to the Loop with these stops along the way to maximize the good cheer.
Get in some holiday shopping at the charming Magic Tree Bookstore (141 N Oak Park Ave, Oak Park; 708-848-0770), a children’s bookstore that’s been a destination for young bookworms from all over the state since 1984. Besides seasonal classics like an illustrated edition of Dickens’s A Christmas Carol, look for locally inspired titles such as Steve Smallman and Robert Dunn’s Santa is Coming to Chicago ($10) or Gina Bellisario’s Twelve Days of Christmas in Illinois.
Conservatory/Central Park Drive
Though it’s still repairing damage from last summer’s nasty hailstorm, Garfield Park Conservatory (300 N Central Park Ave, 312-746-5100), just steps from this stop, is going on with a scaled-down version of its annual winter flower show, this time officially called a Holiday Flower Display in Horticultural Hall. Expect a burst of nature’s holiday color from plants such as unusual varieties of poinsettias and paperwhites. November 24–January 6.
Hop off to check out the West Loop’s shiny new station, which opened in the spring. Then take a short stroll to fuel up at Glazed and Infused (813 W Fulton Mkt, 312-226-5556), where doughnut varieties like maple-bacon long johns and crème brûlée Bismarks intermingle with a rotating roster of seasonal specials, including chocolate peppermint and gingerbread old-fashioned.
Make downtown your final stop, ending the day at the iconic Christkindlmarket (Nov 21–Dec 24 at Daley Plaza, 50 W Washington St, 312-494-2175; free) to eat German delicacies such as schnitzel and strudel, peruse the holiday wares including hundreds of stunning glass ornaments, and maybe persuade Junior to sit on Santa’s lap over at his house by the big tree. This year, there’s also a new Kinder Korner with art-and-crafts activities and passports for kids to take throughout the market to get stamped by vendors, then turned in for prizes.