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Like so many of the best travel anecdotes, this one will start at The Crotch. At least that's what some people are calling the six-corner intersection (Milwaukee, Damen and North Avenues) of the Chicago neighbourhood Wicker Park. On a typical day, a throng of people who care about progressive fashion, music, food and books, plus originality and Pabst Blue Ribbon, spill forth from that intersection, which, in all seriousness, you should really just call The Corners.

Along those three main drags, you'll find a caffeinated, high- and low-end mash-up of DIY creativity, $200 skinny jeans, $2 tacos, new and used books and respectable people watching.

In 1870, Charles and Joel Wicker (a pair of brothers-cum-developers) appropriated 80 acres of land and called it, after themselves, Wicker Park. The devastation following the great Chicago fire, one year later, inspired a real-state boom in their domain, as German and Scandinavian brewery tycoons built their mansions along Hoyne and Pierce Streets, a.k.a. "Beer Baron Row." (For more architectural eye candy, add Caton Street to your walking tour.)

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Poles arrived in the 1940s, adding a cultural imprint that remained strong for decades, even as the neighbourhood declined through the 1970s. (Division Street was known as the Polish Broadway.) Attracted to the low rents and light-drenched warehouse space, artists came next, setting up studios in the historic Flat Iron Arts Building and elsewhere.

Fast forward to the nineties, when an infamous wave of gentrification displaced lower-income residents and the artist pioneers who made the neighbourhood attractive to mainstreamers. Holdouts from those more bohemian days, include Earwax Café and Reckless Records, both icons you shouldn't miss.

For Chicagoans who were there when the neighbourhood was fringe, and even some who weren't, Wicker Park has become synonymous with Faustian-style gentrification. The Wicker-Park-has-sold-its-soul conversation persists to this day, although varied sources are adding nuances: Yes, the countercultural breeding ground is now a, gulp, "destination," but Wicker Park has hardly gone Wal-Mart. The truth is that the neighbourhood's early culture came in concentrated form. So while the forces of urban renewal might have added water (and a Starbucks), Wicker Park never lost its essence. Bottoms up.

Pretty sweet At Mojo Spa, creator and co-owner Amanda Kezios makes 250 all-natural skin-care products. "Call me the Willy Wonka of beauty," she says, referencing her cupcake- and candy-shaped soaps. Mani/pedis use her all-natural products, too. 1468 Milwaukee Ave.; 773-235-6656; www.mojospa.com

Batter up The Bongo Room turns the humble pancake into a culinary movement with flavours like Lemon Ricotta and Blueberry laced with gingersnap brown-sugar butter. Order them in stacks or individually and expect a long to extremely long wait. 1470 N. Milwaukee Ave.; 773-489-0690; www.thebongoroom.com

Free association Reigning purveyor of boho-chic apparel, Free People puts glamour and grunge in a blender and creates something better than either alone. Price points are more chic than boho but worth it. 1464 N. Milwaukee Ave.; 773-227-4871; www.freepeople.com

Starstruck Chef Paul Kahan has just the taco for you (fish, veggie, pork) at the new, honky-tonk inspired Big Star. Other crowd favourites (crowd is an understatement, go early): plantain fries and queso fundido. 1531 N. Damen Ave.; 773-235-4039

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South Asian invasion For a long time, Wicker Park had everything a young urbanite could want/need except for Indian food. Enter Cumin, a new Indian and Nepalese offering. Don't miss the signature drink: Fresh Jal Jeera, with cumin and mint. 1414 N. Milwaukee Ave.; 773-342-1414; www.cumin-chicago.com

Wax poetic Earwax Café's vegan/vegetarian fare is about choices: chicken or seitan, vegan cheese or cheddar. Enjoy it amidst the café's turn-of-the-century, three-ring circus décor. Sword throwers! Fire eaters! Delicious. 1561 N. Milwaukee Ave.; 773-772-4019; earwax-cafe.com

Lenny for your thoughts Brilliant displays make this vintage home store feel like a natural-history museum, only here the exhibits feature mid-century Americana. Lenny & Me Home also has a sister store with vintage clothing across the street. 459 N. Milwaukee Ave.; 773-489-5576

Robin's nest Robin Richman shops Paris and New York to stock her eponymous boutique with haute, hard-to-find selections: Marc Le Bihan's architectural garments, inimitable pieces from Japan's Share Sprit and leather goods by Lebanon's Johnny Farah. 2108 N. Damen Ave.; 773-278-6150; www.robinrichman.com

Retail thera-p.45 P.45 has supported Chicago designers since it opened 13 years ago (when 45 was Michael Jordan's jersey number). Among the more recent designers to appear in the women's boutique: Abigail Glaum-Lathbury, whose sculptural clothing (intricate pleats, origami-like folds) is museum-worthy.1643 N. Damen Ave.; 773-862-4523; www.p45.com

Una Mae I help you? If the gang from the seventies sitcom Rhoda had the chance to stock a 21st-century boutique, they might come up with something like Una Mae's, which mixes incredible vintage finds (with 1970s leanings) and brands on the vanguard, like BB Dakota for women and Free Gold Watch for men. 1528 N. Milwaukee Ave.; 773-276-7002

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Cusack muzak Nick Hornby's 1995 novel High Fidelity took place in London's Reckless Records, but when the movie's script migrated to Chicago (and starred native John Cusack), the beloved Wicker Park branch of the new-and-used music store served as inspiration. 1532 N. Milwaukee Ave.; 773-235-3727; www.reckless.com

Local letters Myopic Books, neighbourhood institution, buys and sells the tomes Wicker Parkians digest. Lose yourself in stacks labelled art, music, film, philosophy, "geek" (comic books) and more. 1564 N. Milwaukee Ave.; 773-862-4882; www.myopicbookstore.com

Drink in the atmosphere Filter's exit from the Flat Iron Arts Building in 2007, when a bank took the spot, caused a period of mourning. Three years later, the coffee shop and all it represented (i.e., the neighborhood's alternative spirit) is back. Drape yourself across a piece of vintage furniture and stay all day. Everyone else does. 1373-75 N. Milwaukee Ave.; 773-904-7819

Triple threat AKIRA, Chicago's newest fashion empire, has three Wicker Park storefronts: men, women and shoes. The vibe is Forever 21-ish, only you won't see everyone and their sister in your new dress. 1814 W. North Ave., 773-489-0818 (women); 1910 W. North Ave. (men); 1849 W. North Ave. (shoes). www.asraigarden.com

Neighbourhood perennial Breathe in the dewy air at Asrai Garden and your whole body smiles. The florist offers hand-tied bouquets to swoon by, plus home goods and fragrant lotions and potions - such as from Florentine perfumery Santa Maria Novella. 1935 W. North Ave.; 773-782-0680; www.asraigarden.com

On a foodie's bucket list No waiters, no hostess, no wine list. It's just chef Michael Carlson at Schwa, plus his kitchen staff and eight tables. The food (and experience) is legendary, challenging and unforgettable to the few who get reservations. Most talked about: quail egg raviolo with truffle butter. Carlson mans the phone. 1466 N. Ashland Ave.; 773-252-1466; www.schwarestaurant.com

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Special to The Globe and Mail

WHERE TO STAY

Wicker Park is close to downtown Chicago, where hotels abound. But the neighbourhood has some of its own options, too.

The Ruby Room Adjacent to her holistic spa, salon and boutique, Ruby Room owner Kate Leydon offers eight guest rooms stocked with Aveda products, spa robes and REM-inducing pillow-top mattresses. Guests can also bliss out in a healing garden in the back. Rates from $159 per night. 1743-45 W. Division St.; 773-235-2323; www.rubyroom.com.

The Wicker Park Inn Five guest rooms offer a bed and breakfast experience (private bathrooms, mind), while three apartments suit the longer-term traveller. The Provence Room is bathed in golden hues, while the Wicker Park Room offers the neighbourhood's signature exposed brick. Rates: $143 (rooms) to $204 (apartments) per night. 1329 N. Wicker Park Ave.; 773-645-9827; www.wickerparkinn.com.

T.M.

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