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A Little Holiday Market Magic

Shop local this holiday season at Wintrust Community Markets! Discover unique, handcrafted finds from Chicago-area artists, makers and small businesses, featuring art, jewelry, apparel, home décor and specialty foods.

Presented by Wintrust, with participating vendors selected from Wintrust and Navy Pier’s Small Business Accelerator Program, supported by BMO, the markets offer a chance to meet local entrepreneurs, explore their work and find one-of-a-kind holiday gifts.

Explore Our Small Business Initiatives

Wintrust Community Markets Schedule

169 NavyPier SlightlySpookyOctober 2026 Markets

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147 NavyPier SlightlySpookyOctober 2026 Markets

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258 NavyPier SlightlySpookyOctober 2026 Markets

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Photo Sep 25 2025, 1 56 58 AM (84) Markets

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Table with colorful jewelry and bracelets

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woman in purple sweatshirt shopping for art

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Sunglasses vendor stall with frames on display at Navy Pier market

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A vendor and customer at Lolita's Bodega Artisan Market.

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A couple observing artwork for sale at Lolita's Bodega Artisan Market.

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