16 Best Places to Shop in The Loop, including the West Loop and South Loop, Chicago

This century-old store is a Loop institution. It's stacked to the rafters with cameras and darkroom equipment at competitive prices.

Twice a year, 200-odd stalls selling clothing, furniture, jewelry, books, and more get treasure seekers' adrenaline flowing. The top-rated event also includes an Indie Designer Fashion Market, showcasing one-of-a-kind wearables by up-and-coming local designers. Weekend admission is $15 at the gate ($12 in advance), and children under 12 get in free.

This boutique’s location in the historic Monadnock Building complements the vintage-inspired clothing, shoes, and accessories it carries.

Travel back to antiquity amid this wondrous trove of classical Greek, Roman, and Byzantine coins and artifacts. Don't miss the gallery rooms in the back.

Iwan Ries didn't just jump on the cigar bandwagon; the family-owned store has been around since 1857. Cigar smokers are welcome to light up in a designated area, which also displays antique pipes. Almost 100 brands of cigars are available, along with 15,000 or so pipes, deluxe Elie Bleu humidors, and many other smoking accessories.

The largest concentration of wholesale and retail jewelers in the Midwest has been housed in this building since 1921, and it's open to the general public. Roughly 190 retailers span 13 floors, offering all kinds of jewelry, watches, and related repairs and services.

This family-owned business, the former Chicago Watch Center, has one of the city's most outstanding inventories of used luxury watches.

The Chicago flagship on State Street, formerly Marshall Field’s, is known for the beloved Walnut Room and iconic holiday traditions like the Great Tree and their magnificent holiday windows as well as for its position as a National Historic Landmark. Macy’s State Street is well known for its architecture and ornamentation; it has a Louis Comfort Tiffany vaulted ceiling, two "Great Clocks" on State Street at Randolph and Washington, the Burnham Fountain, and more. 

Museum reproductions in the form of jewelry, posters, and Frank Lloyd Wright–inspired decorative accessories, as well as books and toys, fill the Art Institute's gift shop. If you're keen on one of the museum's current big exhibits, chances are you'll find some nifty souvenirs to take away.

One of the last establishments of its kind, Optimo makes high-end custom straw and felt hats for men in an atmosphere that evokes 1930s and 40s haberdashery. It also offers a complete line of related services, including cleaning, blocking, and repairs.

Browse through an extensive collection of contemporary art with a special emphasis on folk and outsider pieces at this gallery, which is run by well-known local owners Aron Packer and William Schopf.

Find ethnic and tribal art, including textiles, furniture, and jewelry, at this longtime Chicago favorite.

An enormous warehouse chock-full of leaded glass, garden ornaments, fireplace mantels, bathtubs, bars, and other architectural artifacts draws creative home remodelers and restaurant designers from around the country.

Board of Trade types who like special attention and the perfect fit come to this legendary clothier for brands like Giorgio Armani and Ermenegildo Zegna. Home and office consultations are available.

Live, usually themed, auctions occur on Saturday mornings about once a month. Preview items are also displayed on the floor for immediate sale at a set price. Preview hours are typically Monday through Saturday 10–5 the week before the auction.

This local fave hit the big time by becoming a staple in Academy Awards gift bags. Try exotic chai-infused, peppermint pistachio, and lavender-vanilla toffee—or stick with the irresistible almond-and-pecan McCall's Classic, named for owner Terry Opalek's grandmother, whose recipe inspired the entire operation. There's a second location on the first floor of the Galleria (5247 N. Clark Street).