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Windy City chic

Looking for a weekend escape or girlfriend getaway? Along with sleek architecture and a sparkling lakefront, Chicago boasts stunning hotels, inventive restaurants and world-class shopping — making it one of the most vibrant North American cities today.

Chicago, known as the “Windy City” and the “Second City,” is perfect for a quick weekend jaunt that requires less than five hours travel by plane from major cities like New York, Miami and Los Angeles. From restaurants to shopping, here’s a list of our best picks.

Where to stay

JW Marriott Hotel

The landmark downtown JW Marriott Hotel is designed by renowned architect Daniel Burnham, and guests will immediately notice its elegant decor. The hotel includes a wellness center and indoor pool, or for a truly relaxing experience, visit Valeo spa, home to the only Clarity Chamber in the U.S. For the ultimate girlfriend getaway, book a weekend spa package including two 60-minute spa treatments. The package ranges from $429 to $879; daily night rates without spa treatments start at $174 per night.

Hotel 71

Perhaps the coolest boutique hotel in the city, Hotel 71, is both modern and charming. The guestrooms and suites (which include free Internet) offer views of the city or the Chicago River. Luxury details include oversized marble bathrooms in the guestrooms, some with rainforest showers. Deluxe City View rooms start at $139 per night, while Premier City View rooms start at $159 per night. For gals seeking major retail therapy, why not consider the Hotel 71 Shopping Package, which includes a $50 gift card per every two nights of stay and a $20 food and beverage credit per day.

Where to eat

Henri - Chicago
You’ll feel like you’re in Paris when you dine at Henri. The French-influenced and seasonal menu, overseen by Executive Chef Dirk Flanigan, offers a $25 three-course lunch menu ideal for ladies who lunch and travelers alike (think foie gras and croque monsieur). The stylized decor reflects the building’s turn-of-the-century roots with mohair settees and velvet-covered walls.
Foodies will love Lockwood, which is known for farm-to-table dining. The restaurant is situated in the historic Palmer House Hilton. What to expect? Executive Chef Greg Elliot focuses on seasonal and regional products, even growing his own fruits, vegetables and herbs on the rooftop garden. The ever-changing menu recently featured house-made ricotta ravioli and organic Shetland salmon.
GT Fisher
GT Fish & Oyster continues to draw the socialite and celebrity crowds as chef Giuseppe Tentori creates a menu that deliciously walks the line between traditional and contemporary cuisine. The menu items range from French Osetra caviar and clam chowder to fish tacos and braised short ribs.

Where to shop

Shopping bag

The options in Chicago are endless — from the famous Magnificent Mile, home to major stores like H&M and Macy’s, to boutique shopping in ultra-hip neighborhoods. Here are our must-have visits:

Seeking serious fashion? Visit Ikram, featuring the most impressive selection of designer clothing, from Chanel and Comme des Garcons to Givenchy and Jason Wu, this side of the Atlantic. The store also has a farm-to-table restaurant, with light fare — perfect to ease the hunger pains that arise from starvation shopping.

Head west to Damen Avenue, where Bucktown is home to a plethora of brand-name shops. These include Nanette Lepore, known for pretty and feminine styles; Cynthia Rowley, featuring fun clothes and accessories; Alexis Bittar, creator of fabulously modern earrings, bangles and earrings; and Marc by Marc Jacobs, where you’ll find a large collection of accessories, shoes, and handbags and collection pieces.

Where to cocktail


No girlfriend getaway is complete without a cocktail break. Rebar, situated in the mezzanine level of Trump International Hotel & Tower Chicago, is known for its outstanding cocktails. Sip on a Red Dragon or Kiwi Kick, while taking in the breathtaking views from the 30-foot floor-to-ceiling windows. But do dress up — this see-and-be-seen lounge attracts a bevy of well-heeled locals, hotel guests and socialites.

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