Chicago shopping runs far past the Magnificent Mile. Three days here move from Randolph Street's flea stalls and Milwaukee Avenue resale to Andersonville's Swedish-rooted independents, the Merchandise Mart's design floors, and small-batch makers packing everything from Malört to Marshall Field's Frango mints.
Indoor-outdoor antiques and vintage fair on the Plumbers Hall grounds at 1341 W Randolph, running one weekend a month roughly May through October plus winter indoor editions. Around 200 dealers sell mid-century furniture, costume jewellery, vinyl and Americana signage.
Year-round indoor market hall under the Ogilvie Transportation Center at 131 N Clinton, open weekdays about 07:00-19:00 and Saturdays until 17:00. Around 30 stalls: Pastoral cheese, Fumare pastrami, Delightful Pastries kolacky and City Fresh produce.
Factory shop at 600 W Kinzie beside the plant whose cocoa smell has scented River North since 1939. Open weekdays only, roughly 09:00-17:00, selling bulk baking chips, bars and broken-batch chocolate at wholesale prices you won't find in any downtown gift shop.
German-founded pharmacy at 4716 N Lincoln, trading since 1875, with dark wood cabinets holding European soaps, badger shaving brushes, Klar seifen, herbal tinctures and hard-to-source scents. Open until about 18:00 most evenings, Sundays shorter.
The densest resale corridor in the Midwest between North and Division: Kokorokoko for 80s-90s neon, Una Mae's for curated denim, Buffalo Exchange for trade-in racks and Knee Deep Vintage nearby. Most doors open 11:00-19:00, some at 12:00.
Three floors of used books at 1564 N Milwaukee, open since 1991 and running until 21:00 or later most nights. Around 80,000 volumes, strong in philosophy, poetry and Chicago history, with creaking stairs and a no-mobile-phone-conversation policy.
The 4.2-million-square-foot Art Deco block at 222 W Merchandise Mart Plaza, built 1930 and once the world's largest building. Floors 1-2 are open retail plus LuxeHome kitchen and bath showrooms; upper trade floors open to the public during design fairs.
Vast furniture and objects store at 1885 N Clybourn mixing new upholstery with European antiques, garden urns and seasonal florals. Open to about 18:00 weekdays. The rear vintage room is where Chicago interior designers actually source one-off pieces.
Historically Swedish stretch of N Clark between Foster and Bryn Mawr with one of the country's highest concentrations of independent shops: Wikstrom's Scandinavian goods, Scout for salvage decor, Brimfield for wool blankets. Doors open 10:00-11:00.
The former Marshall Field's flagship at 111 N State, opened 1907, with its Tiffany Favrile glass ceiling and clocks. The seventh-floor Walnut Room and the ground-floor Frango mint counter are the two things worth the trip inside.
Shop at 111 E Wacker stocking skyline-print textiles, Frank Lloyd Wright reproduction glass, terracotta fragments cast from demolished buildings and the best selection of Chicago architecture books anywhere. Open daily, roughly 10:00-17:00.
Sprawling liquor warehouse at 1132 S Jefferson stocking the full range of Chicago-made spirits: Jeppson's Malört, Koval whiskey, CH Distillery vodka and Half Acre or Revolution beer in cans that survive a suitcase.