Start your shopping trip at American Girl Place, where grandmothers, moms and daughters alike will be enchanted by the collection of historical and contemporary dolls. Each doll has a story, told through the accompanying books written for preteens. Girls can have a photo shoot with their dolls, take their doll to a hair salon or even brunch with th... Moreeir dolls at the American Girl Place Cafe. Buying new outfits and accessories for the dolls can quickly add up though, so be careful not to spend everything at your first stop!
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American Girl Place
835 N. Michigan
Chicago
877-247-5223
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Hours
Monday-Thursday 10am-7pm
Friday-Saturday 9am-9pm
Sunday 9am-7pmLess

Adjacent to American Girl Place is the Water Tower Place shopping center. Check out CUSP, Neiman Marcus' fresher, hipper sister boutique. Other specialty stores include Betsey Johnson for funky fashion, Lacoste for classic sportswear, lucy for yoga clothes and Francesca's Collection for affordable trends. AKIRA is the resident local Chicago boutiqu... Moree.

Of course, you can also shop at the tried-and-true national chains like Abercrombie & Fitch, Banana Republic, Nine West and Ann Taylor. Or freshen up with a makeover and beauty essentials at Sephora or Bare Escentuals.
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Water Tower Place
835 N. Michigan
Chicago
312-440-3166
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Hours
Monday-Saturday 10am-9pm
Sunday 11am-6pmLess

Cross the street for some bargain designer finds at Filene's Basement. Pick up designer department store brands like Armani, Gucci, Via Spiga, Guess and Hugo Boss for up up to 75 percent off the original retail price. When your friends ask, you can say you bought your trendy handbag on the Mag Mile in Chicago—without mentioning that it came from an... More off-price retailer.

For even more bargain shopping, Brit fast fashion favorite Topshop will be moving into the old Borders space next door in fall 2011.
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Filene's Basement
830 N. Michigan
Chicago
312-482-8918
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Hours
Monday-Saturday 9am-9pm
Sunday 10am-7pmLess

Keep walking north along the Mag Mile and you'll reach an even more upscale shopping center—Shops at 900 N. Michigan Ave.

Anchored by a Bloomingdale's department store, this mall caters to the high-end shopper, with Michael Kors and MaxMara boutiques. Space591 is an eclectic boutique worth visiting, with women's and men's clothing as ... Morewell as home furnishings and other fun accessories.

And stop by the tiny Fogal boutique on the first floor, the luxury Swiss hosiery company's only U.S. location outside of New York City.
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Shops at 900 North Michigan
900 N. Michigan
Chicago
312-915-3916
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Hours
Monday-Saturday 10am-7pm
Sunday Noon-6pmLess

At this point, your feet may be getting tired. So take a break and freshen up at one of the top powder rooms in the world at the Drake Hotel, straight out of a 1940s movie. As you enter the Palm Court tea room, the powder room is directly to your left. Each stall has its own sink, stool and mirror.

When you're camera ready, step out t... Moreo enjoy afternoon tea, served 365 days a year with live harp music. Countless celebrities and heads of state have stayed at the Drake, including Princess Diana, Elizabeth Taylor and Frank Sinatra. You'll feel like nobility yourself as you munch on French pastries and sip your tea—pinkies out!
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The Palm Court at the Drake Hotel
140 E. Walton Place
Chicago
312-787-2200
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Hours
Daily 1-5pm
Less

If tea and pastries doesn't quite cut it and you're looking for a more substantial meal, simply cross the street for the best Italian food in the city.

Spiaggia is President Obama's favorite date-night restaurant, but it can be pricey. You can get the same food cooked in the same kitchen for a fraction of the price at the less-formal ... MoreCafe Spiaggia. The two are located in the same building, right at the corner of Michigan and Oak.
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Cafe Spiaggia
980 N. Michigan
Chicago
312-280-2750
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Hours
Lunch
Daily 11:30am-2:30pm
Dinner
Monday-Thursday 5:30-9:30pm
Friday-Saturday 5:30-10:30pm
Sunday 5:30-9pmLess

After a delicious meal, it's finally time to turn onto Oak Street—the ritziest shopping street in town.

Stop in at Sofia Vintage for a one-of-a-kind selection of vintage designer clothing. Nicole Richie, Gossip Girl's Leighton Meester and Juliette Lewis are all big fans of this independent boutique. The selection is small but constant... Morely changing, and there is a nice sale section in the back of the store. Don't be intimidated— the owner is quite nice and not at all pretentious.
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Sofia Vintage
72 E. Oak
Chicago
312-640-0878
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Hours
Monday-Saturday 11am-7pm
Sunday Noon-5pmLess

Hopefully you've saved room for dessert. Stop by Sarah's for a decadent treat and the only affordable shopping on Oak Street. Her wedding cakes have appeared on the cover of Brides Magazine and both Oprah Winfrey and Martha Stewart love her chocolates and brownies.

Try the chocolate raspberry brioche and ask to have it microwaved for ... Morea few seconds so the inside becomes properly gooey.

On a hot day the fresh-squeezed lemonade here really hits the spot.
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Sarah's Pastries & Candies
70 E. Oak
Chicago
312-664-6223
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Hours
Monday-Saturday 8am-6pm
Sunday 10am-6pmLess

The Denim Lounge was voted the best denim store in Chicago by Time Out Chicago Magazine.

Get a glimpse of your backside in high definition with the famous HD butt cam as you try on more than 20 designer brands of men's and women's denim like Citizens for Humanity and Seven for all Mankind. No need to ask your shopping companions how y... Moreour butt looks in your jeans—just check it out yourself on the big screen above the mirror.

The stylists here will be straight with you too—with the store's huge selection of brands and styles, there's something for every body type.
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The Denim Lounge
43 E. Oak
Chicago
312-642-6403
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Hours
Monday-Saturday 10am-6:30pm
Sunday Noon-5pmLess

You may want to do a little plastic surgery (cutting up your credit card) before entering Hermès' new 6,000-square-foot flagship store on the corner of Oak and Rush.

Hermès may be most famous for its beautiful silk scarves and handcrafted Birkin handbag, made famous on "Sex and the City," but you'll also find ties, jewelry and small l... Moreeather accessories galore. If you're likely to purchase a Birkin, just ask one of the sales associates if they have any in stock. The rumored multiyear waiting list for the coveted handbags is just that—a rumor.

This location opened in 2010 and the interior is designed after the original Hermès in Paris.
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Hermès
25 E. Oak
Chicago
312-787-8175
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Hours
Monday-Saturday 10am-6pm
Sunday ClosedLess