Passport To Chic: Chicago

Passport To Chic: Chicago

April 20162957Views

Shopping, tea, and sailing in the Windy City

I am going to be a bridesmaid in a friend’s wedding and ever since I received this invitation I’ve been on a mission to book a flight, arrange accommodations, find the perfect dress—she graciously let us pick styles befitting our look and style—and discover all there is to know for an excursion to the Windy City.

From an afternoon tea at a historical hotel to a river boat cruise to see the city’s architecture—there’s so much to explore, and from all the intel I’ve been gathering, it looks like Chicago might be one of the best vacations spots for shopping, dining, and sight-seeing. Here’s what you can put on your radar if you plan to visit Chicago.

What to Pack: Make sure you bring along essentials for the season. It’s quite hot in the summer and can be humid, while the winter is the polar opposite—extremely cold and snowy. A must have for Chicago or any other travel destination is comfy, yet chic shoes. Perfect for this vacation are the Burberry London leather and canvas brogues. These two-tone kicks are reminiscent of what prohibition era gangsters might have worn—every girl needs a little haberdashery-inspired gear in closet.


Where to Stay: Chicago is known for its historical hotels and The Drake Hotel, which opened on New Year’s Eve in 1920, is at the top of that list. During the Roaring Twenties, the elite hotel was the “it” place for high-society and a few decades later newlyweds Marilyn Monroe and Joe Dimaggio would carve their iconic initials into the bar’s world famous wooden counter. Today, the iconic hotel offers afternoon tea in their Palm Court (below) and a 10-floor tour of the historical hotel. This is definitely on my radar!


What to do: Known for its architecture, a great way to see the Windy City and its beautiful buildings is by boat on Chicago’s First Lady. The 90-minute daily river tours are in collaboration with the Chicago Architecture Foundation, so you’re sure to see the best of what the city has to offer.


Where to shop: For an artsy shopping experience, you might want to check out Ikram, who’s known for carrying an eclectic mix of designer fashions from around the world. The boutique has a brilliant red storefront and features designer brands from Moschino to Valentino. There’s even an art gallery and cafe on site!


Image source:,, and

Mignon Gould

Mignon Gould

Mignon Gould is a multimedia publisher and the Agent-in-Chief of She is a style enthusiast, who views fashion as an art form that anyone can master. In our Culture column, she shares her musings on the latest happenings in the world, from diversity in fashion to pop culture controversies. Mignon has also interviewed celebrities and insiders including actress Emma Stone, 70's supermodel Pat Cleveland, and Audrey Hepburn's son, Luca Dotti.

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