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1923 W. Division St.; 773-772-9088
SAVE This store’s jumbled mix of men’s and women’s clothing can be difficult to parse. But we love Public I’s luggage, seemingly picked for compactness, durability, and thoughtful design features. No run-of-the-mill Samsonite wheelie bags here; instead, you’ll see International Traveler’s semi-hard-sided polycarbonate cases in sunny colors—such as turquoise, red, and lime green—that are perfect for kids (also available in more adult-friendly black and silver). The 21-inch suitcase goes for $98.
1133 N. State St.; 312-944-1001
SPLURGE This New York City–based travel boutique opened on the Gold Coast last year and quickly took its place as the go-to spot for travelers who love elegant design. The brands sold here are mainly imports from design-obsessed countries such as Italy, Germany, and Japan, goods that you would otherwise have to hunt for around town. Our favorite find? The 30-inch Work trolley by the Italian bag maker Mandarina Duck (pictured; $465), which has a partially removable suiter with three hangers and two zippered pockets inside.