Some folks chase Santa during the holiday season. Others chase sales. This week, Chicago bookworms are chasing tickets for the inaugural Chicagoland Bookstore Holiday Trolley like it’s the Polar Express for introverts. With special swag, 10 unique routes and promises of can’t-miss deals and seasonal surprises, it’s the kind of festive outing that reminds you why books still make the best gifts—especially the ones you buy for yourself.
The Chicagoland Bookstore Holiday Trolley is a an endeavor by the Chicagoland Independent Bookstore Alliance, which is comprised of 43 indie bookstores across Chicago and its neighboring bookish suburbs. In hopes of driving sales and promoting a sense of community among book lovers this holiday season, the trolley offers 10 different routes to choose from; and each route includes stops at four to five bookstores. Adding to the variety, each route has a unique starting location and duration.
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This initiative couldn’t have better timing: WTTW reported earlier this month that local businesses are experiencing revenue drops akin to pandemic-era sales slumps. Factors including the onset of “Operation Midway Blitz,” increased ICE presence throughout the city and whispers of a possible recession have all negatively impacted local businesses throughout the city.
“This work serves as a reminder that community third spaces like indie bookstores—and the people who support them—will always have more to offer than big box stores and online giants like Amazon,” a spokesperson for the Chicagoland Independent Bookstore Alliance says. “It’s important to support independent bookstores and other small businesses during the holiday season. Especially if you want to see us around next year.”
The trolley rides will take place on weekends throughout December, and each trolley will be equipped with a unique host aboard to emcee the experience. Each bookstore will be stocked with a wide selection of handpicked reads, unique gifts and a few holiday-themed surprises. Some of the bookstores on the routes include: Hyde Park mainstay Seminary Co-op, Spanish language and bilingual bookstore Los Amigos Books, horror-centric book and record shop Bucket O’ Blood Books and Records, and Andersonville’s theater-themed book shop The Understudy.
“Bookstore workers are coming up with such fun ways to sprinkle in holiday magic for the trolley participants on their routes,” the Chicagoland Independent Bookstore Alliance spokesperson says. “And I think it’s safe to say that we’re all looking forward to the joy and connection that this event brings, especially as things have been really challenging for many of our communities in Chicago.”
By the end of the trolley ride, everyone will surely be carrying to many books and promising themselves in vain they won’t buy any more until the New Year. But that’s the point: for one blissful winter afternoon, Chicago readers get to feel like kids at the Scholastic Book Fair again—just older, colder and slightly better read.
As of publication, tickets for all trolley dates are available here and cost $52 per person. Bibliophiles are advised to act fast, though: According to the Chicagoland Independent Bookstore Alliance, within 48 hours they’ve so far sold 250 tickets across 10 trolley routes. Learn more about the Chicagoland Independent Bookstore Alliance here.

