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Shopping the Magnificant Mile and Oak Street

Where to save and splurge in this high-end shopping area
Difficulty: Easy
Length: 0.5 miles
Duration: Half day

Overview :  Start at the corner of Chicago and Michigan avenues so you can snap a few photos in front of the historic Water Tower. Built in 1869, ... more »

Tips:  Parking in this area is expensive, so taking public transportation or walking may be your best bet. And after a long day of shopping, ... more »

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Points of Interest

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... More

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... More

3. Filene's Basement

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... More

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 well as... More

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 to enjoy... More

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 Cafe... More

7. Sofia Vintage

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 constantly changing... More

8. Sarah's Pastries & Candies

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 a few... More

9. The Denim Lounge

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 your butt... More

10. Hermès

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 leather... More