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There's Nothing Like the Big City: Chicago

When was the last time you wore heels? The last time you went dancing—other than at a wedding? The last time you ate at a restaurant without crayons on the table? The last time you stayed up past midnight?

Shops You Can't Find Everywhere
Lori's Designer Shoes: This flagship of a five-location chain stocks Aerosoles along with more niche designs like Castañer espadrilles and 100% boots.

Lili Boutique: Great service and a selection of upscale women's clothing. Highlights include Twinkle tops and dresses, edgy accessories like Dolce Vita shoes and Rebecca Minkoff bags, and designer denim by Earnest Sewn.

Akira: Fun, funky clothes, from designer jeans to $20 blouses, with a wide range of prices and labels, including Hudson, Free People, and Frankie B.

Vive la Femme: For the latest looks exclusively in sizes 12-24, including dresses, jackets, pants, tops, and skirts by Jessica Svoboda and Anna Scholz.

Lenny & Me: An unpretentious consignment shop that's especially good for sexy retro dresses, screen-printed tees, and decades-old accessories.

You Gotta Do at Least One…
Gawk at 50 landmarks during the Chicago Architecture Foundation's 90-minute river cruise.

Catch a show at Second City, the comedy club that launched the careers of Tina Fey, Mike Myers, and Amy Sedaris.

Watch the Cubs from Wrigley Field's bleachers, where fans buy each other rounds of beers--making it like the world's largest singles bar.

What's for Dinner?
Rick Bayless cooks authentic Mexican at his world-famous Frontera Grill.

The innovative and mostly vegetarian menu at Green Zebra consists of small plates such as crispy sweet-potato dumplings with water chestnuts and dandelion miso broth.

Japonais is a dimly lit French-Japanese restaurant and lounge. Good for sharing: Le Quack Japonais, a take on Peking duck.

After a kitchen fire in 2006, Pequod's traded its neon signs and White Sox mural for hardwood floors, exposed brick walls, and plasma TVs. Luckily, its thin-crust and deep-dish pizzas stayed absolutely the same. They're served atop whale-shaped boards.

 
Note: This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.
 

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