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While the Windy City may be known for its chichi shopping along the Magnificent Mile, aka Michigan Avenue, those young and in the know go off Chicago's beaten path to the trendy Bucktown/Wicker Park neighborhood for a truly edgy, urban experience. Gritty and glam, Damen and Milwaukee Avenues and off-shoot Division Street are teaming with small, eclectic boutiques and new specialty shops that sprout up seemingly every month.
A shopping trip to Bucktown would not be complete without visiting p.45 at 1643 North Damen Avenue. Pioneering both in its location and its fashion, p.45 introduced Rebecca Taylor to the city when it opened in 1997. Now, it champions local talent, selling innovative pieces by School of the Art Institute grads Lara Miller and Shane Gabier as well as beloved Splendid T-shirts and Michelle Mason dresses. Up the block lies Hejfina, at 1529 North Milwaukee Avenue, a new haven for everything modern, from books, art, shoes and women's and men's apparel to custom-made furniture by local designers. Further south, fun fuses with fashion at Penelope's, 1913 West Division Street, where shoppers can check out youthful frocks from Built by Wendy and tailored basics by A.P.C. while hanging with the owners' two pugs or playing an old Ms. Pac-Man video game.
After all that shopping, slip into the sleek surroundings at Japonais, at 600 West Chicago Avenue, and keep your eyes out for stars: Cameron Diaz, Eva Longoria, Sharon Stone, Zac Posen and Narciso Rodriguez have all enjoyed the Asian restaurant's rich, deep red- and gold-accented ambience as well as its sake and sushi. Make sure to visit the breezy, candlelit, outdoor terrace overlooking the Chicago River. Later, consider cocktails at reserve. Part club, part lounge, the nightspot is equal parts warm and exotic, marked by bamboo, brushed copper, dark wood accents, leather daybeds and a theatrically lit back bar. Rest rooms feature complimentary champagne in the women's lounge and a waterfall in place of urinals in the men's room.
For the young and fun, the W Hotels are the place to stay. Most opt for the W Chicago-Lakeshore, at 644 North Lakeshore Drive along Lake Michigan, with its lake views and proximity to Oak Street beach and Michigan Avenue shopping. The W Chicago-City Center, at 172 West Adams, boasts a dark, dramatic entrance with intimate alcoves for late-night rendezvous. For more lush surroundings, the Peninsula Hotel, at 108 East Superior Street, offers expert service, upscale accommodations and delectable dining options, as well as Friday afternoon teas with a fashion theme. Don't miss the Peninsula spa, a favorite among locals and visitors, and the top-floor pool surrounded by floor-to-ceiling windows providing a striking view of the city.