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Quimby's
The epicenter of Chicago's comic and zine worlds, Quimby's is one of the linchpins of underground culture in the city. You can find everything here from crayon-powered punk-rock manifestos to slickly produced graphic novels.
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Reckless Records
Chicago's best indie-rock record and CD emporium allows you to listen to everything before you buy. If you're looking for CDs by local bands like Tortoise or Gastro del Sol, come here first.
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Red Balloon Co
When hipsters get good jobs and start having kids, this is where they outfit the li'l pups. Adorable clothes, classic children's books and '50s-ish toys prevail in the cozy space.
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Renegade Handmade
This store sprung up out of a popular local craft fair. Rather than just selling their goods for two days per year, participants thought it would be a swell idea to have an outlet to sell from year-round. Bravo! The reasonably priced merchandise veers toward mod, such as bo-ho tops, graphic-print guitar straps, journals reconstructed from vintage hardback cookbooks and shadow puppets (why not, eh?).
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Rock Records
Don't let the sometimes surly staff scare you away from this well-stocked independent record store, which has a good number of listening stations and a wide selection of pop, indie rock, hip-hop and country.
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Sam's Wine & Spirits
Cavernous Sam's carries Chicago's largest selection of imported vino. It's easy to spend hours chatting with the informative staff and loading up for future dinner parties. Tastings occur a few times each month, usually on Tuesday or Wednesday evenings. Beer, spirits, champagne and cheese are sold en masse, too.
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Self Conscious
Chicago Bears players, Bulls players and rappers browse through the hoodies, track jackets and T-shirts in this converted West Loop warehouse. The bling-y, limited edition Adidas and Nike shoes are the main attraction, such as the crocodile-and-Italian-leather Nike Air Force Ones, complete with an 18-karat gold shoelace bauble.
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Seminary Cooperative Bookstore
This is the bookstore of choice for several University of Chicago Nobel Prize winners, including Robert Fogel, who says, 'For a scholar, it's one of the great bookstores of the world'. The shop is owned by the same folks as 57th St Books.
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Shops at North Bridge
The newest of the classy Michigan Ave malls, Shops at North Bridge appeals to a less aggressively froufrou demographic with stores like the Body Shop, Ann Taylor Loft and the LEGO Store. The multilevel mall connects anchor department store Nordstrom to Michigan Ave via a gracefully curving, shop-lined atrium.
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Sports Authority
In a classic rags-to-riches story, Morrie Mages got his start in his family's store in the old Maxwell St Jewish ghetto, where some of the city's leading retailers launched their careers by selling clothes between WWI and WWII. Mages built this into the world's largest sporting goods store, eventually moving it from Maxwell St into its own renovated eight-story warehouse here.
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Sports World
This store across from Wrigley Field overflows with - that's right, Sherlock - Cubs sportswear. It carries all shapes and sizes of jerseys, T-shirts, sweatshirts and ball caps, plus baby clothes and drink flasks. Surprisingly, the prices aren't bad given the attraction-side location.
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Strange Cargo
One of the coolest stores in Chicago for retro T-shirts and thrift-store-esque hipster wear, Strange Cargo also sells wigs, clunky shoes and leather jackets. Buy a vintage-style T-shirt, then use the iron-on machine to enliven it with a message or decal of your choice. There's an excellent selection of kitschy ones featuring Mike Ditka, Harry Caray and other local sports heroes, which make top souvenirs.
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T-Shirt Deli
They take the 'deli' part seriously: after they cook (aka iron a retro design on) your T-shirt, they wrap it in butcher paper and serve it to you with potato chips. Choose from heaps of shirt styles and decals, of which Mao, Sean Connery, Patty Hearst and a red-white-and-blue bong are but the beginning.
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Ten Ren Tea & Ginseng Co
Ten Ren is the place to buy green, red, white and black teas, plus the teacups and teapots to serve them in. They also sell thirst-quenching bubble teas at the counter.
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Threadless
Threadless has a unique business plan. First, it runs an ongoing t-shirt design competition on its website, in which designers submit ideas and consumers cast votes (750,000 weekly). The company then releases the seven winning styles in limited quantities of 1500, and they're only available for two weeks. The new designs appear in-store on Fridays, before they're posted online on Mondays.
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Tommy's Rock & Roll Café
Located at the edge of Ukrainian Village, Tommy's is hands-down the most rawkin' guitar store in town. So grab a doughnut or a Polish sausage at the tiny front café, then strum (after you wash your hands!) the vintage axes in all their polka-dotted, snake-skinned, heart-shaped and Darth Vader-painted glory. Elvis impersonator photos, letters from Tom Petty, big-ass amps and a whole lot of handcuffs ratchet up the entertainment.
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Una Mae's Freak Boutique
It's unlikely that the solid suburban women who once wore the pillbox hats and fine Republican cloth coats on sale here would ever have thought of themselves as freaks. Along with the vintage wear, Una Mae's has a growing collection of new accessories like scarves, hats and cosmetics.
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Uncle Dan's
The smell of leather hits you in the face as you walk into this outdoor gear store, offering a big selection of hiking boots and equipment, plus camping supplies and many brands of backpacks. It's a relaxed place to buy outdoor gear, without the derisive looks of lurking sales dudes who consider anything less than a frontal assault on K2 to be for wimps.
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Uncle Fun
This weird toy and novelty shop is one of the best spots in Chicago for goofy gifts, kitschy postcards and vintage games. The shelves are overflowing with strange finds like fake moustache kits, 3-D Jesus postcards and Chinese-made tapestries of the US lunar landing.
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Us #1
From the outside this place looks like a dump. Inside, however, you'll find rack after rack of affordable, vintage '70s bowling, Hawaiian and western-wear shirts, as well as towers of old Levis jeans.
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Vive La Femme
Plus-size shops for women are often woefully lacking in style. Not so at Vive La Femme, where larger women can find sassy and classy designs in sizes 12 to 24.
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Vosges Haut-Chocolat
Owner/chocolatier Katrina Markoff is making a huge name for herself by whipping up truffles, ice cream and candy bars with exotic ingredients like curry powder, chilies and wasabi. They sound weird but taste great, as the abundant samples laid out along the back counter prove (though the simplest concoction of the bunch - the dark-milk-chocolate-and-sea-salt Barcelona Bar - remains the sweet to beat).
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Water Tower Place
Featuring the coolest fountain in all of Chicago mall-land (you'll see it on your ride up the main escalator), Water Tower Place launched the city's love affair with vertical shopping centers. Many locals swear this first one remains the best one. The mall houses 100 stores on seven levels, including Abercrombie & Fitch, Sharper Image, the Limited, Express and Macy's.
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Wikstrom's Gourmet Foods
Scandinavians from all over Illinois flock here for homemade limpa, herring and lutefisk. It sells over 4000lb of Swedish meatballs around Christmas time.
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Windward Sports
One-stop shopping for sporty gear, whether you're into windsurfing, in-line skating, snowboarding or the see-it-to-believe-it 'flowboarding' (kind of like a cross between skateboarding and snowboarding). Ask at the store about various beach rentals of windsurfing equipment during the summer.
