Holiday shopping is supposed to be joyful in the same way that assembling Ikea furniture is supposed to be quick and easy: theoretically true, but rarely confirmed in practice. The pressure to find the perfect gift can drive even the most thoughtful person to doomscrolling gift roundups at 1am, convinced that nothing less than a hand-carved, ethically sourced heirloom will properly convey affection. Add in cryptic shipping deadlines and a litany of discount windows and suddenly buying presents feels less like an act of endearment and more like an endurance sport.

This guide aims to simplify your holiday shopping while supporting stores within Chicagoans’ reach (and most of them offer online options, too). Because shopping local shouldn’t feel like homework; it should feel like finding a t

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