Chicago’s most festive treasure hunt returns just in time for the holidays. The Randolph Street Holiday Market pops back up November 15–16, 2025, from 10 a.m. to 5 p.m. both days, transforming the West Loop into a sparkling wonderland of vintage scores, modern finds and one-of-a-kind handcrafted gifts. Long considered Chicago’s can’t-miss seasonal shopping tradition, the market invites style-seekers, collectors and holiday enthusiasts to explore 125 mini-boutiques bursting with fashion, décor, jewelry, art, entertaining essentials and unexpected delights you won’t find anywhere else.

This year’s edition promises a true holiday mood-lift: sip creative cocktails, sample fancy foods, and catch informal modeling while DJs keep the energy high. Families will find plenty to enjoy, from the

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