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 treasure you didn’t know you needed, offered by someone who is genuinely glad you walked through their door.
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The Center of Order and Experimentation
1727 W Grand Ave
If Wes Anderson designed a cafe-meets-gift shop, it would probably look a lot like the Center of Order and Experimentation. Step inside and you’re greeted by a velvet-upholstered counter, sticker-covered clipboards and sleek, futuristic-font signs declaring the space is “not a cult.” Along with niche items—like cake-shaped candles, fluorescent tea boxes and handmade ceramics from local makers—COE is hosting a slew of holiday activations, including custom foil embossing, stunning gift wrapping options and extended hours for the procrastinators among us.
Homegrown Studio
1011 W 18th St
Open for just a few months so far, Pilsen’s Homegrown Studio is already making headlines for its eclectic curation and locavore sensibilities. Stocking wares from over 30 local curators and makers, Homegrown’s inventory covers every possible interest and hobby, including wearable art, skincare, sourdough starter kits and art prints. What’s more, there’s no consolidated register at Homegrown: Customers purchase items by paying the artists directly via electronic payment. Follow Homegrown’s Instagram to stay updated on holiday offerings, like product roundups and workshop announcements.
Festive Collective
2643 N Milwaukee Ave
Chicago entrepreneur Angela Wator opened Festive Collective to sling her own line of party supplies, but it didn’t take long for the colorful space to transform into a retail destination for all things nostalgic, niche and, yes, festive. For the past decade, the Festive Collective has transformed its space for a themed holiday shop. This year’s theme is Tinseltown: Colorful garland hangs from the ceiling like weeping willow branches, eccentric ornaments are available for purchase (think the Beatles’ yellow submarine and blushing kewpie doll heads) and plenty of other gifts that will induce oohs, ahhs and jealousy from family members are available.
Bon Femmes
4917 N Damen Ave
Omotola Akinbiyi began with a blog where she interviewed women artists and creatives. Soon, she realized these artists needed a brick-and-mortar space to reach new audiences, leading her to open Bon Femmes in 2021. An added bonus: The shop also prioritizes sustainability, with 95% of its packaging being recyclable. Bon Femmes’ holiday shop is stocked with perfect gifts for the fashionista or creative in your life, including nail art stickers, ceramic ornaments and cozy wool socks ideal for the oncoming chill of winter.
Ándale Market
5232 N Clark St and 725 W Wrightwood Ave
For the foodie in your life, Ándale offers the perfect gift. The shop, which is a “love letter to the bodega,” stocks all things food and drink, from preparation to execution. Inventory includes rainbow-hued cutting boards, cookbooks, Ibérico ham chips and premium CBD drinks. For the ultimate holiday gift, pick up an Ándale Market Box. These pre-packed gift boxes are curated with fun themes like “Fishy Faves” (a cigar box packed with tinned fish sourced from across the globe) and “Pizza Night” (a bundle of artisanal pizza ingredients complete with a recipe card).