Girl Time in the Windy City

Chicago Athletic Association

Until a couple years ago, the “Forever Marilyn” statue, a 26-foot-tall statue depicting Marilyn Monroe in her iconic pose from the 1955 film Seven Year Itch watched over Chicago’s Magnificent Mile. Always a perfect backdrop for tourist photos, the giant Marilyn with her billowing, white dress has always been a little provocative and frequently elicits some fascinating political discussions.

For those of us who love Marilyn, pleated white dresses, and old movies, it’s impossible to resist standing beside her for a quick photo or two. Sadly for those who plan on a trip to the Windy City, the installation has moved on, and now lucky fans in Australia have the privilege of looking up Giant Marilyn’s dress. Chicago has plenty of other opportunities for ladies on the go, but keep in mind that it really is “the windy city,” so leave the white dress in the closet in favor of something a little less likely to blow upwards.

In the hit show “Sex and the City,” Carrie and her gal pals had their favorite restaurants, cafes, bars and nightclubs in the trendiest parts of Manhattan, where they sipped cosmos and talked about their impossibly unrealistic lives. Seriously, a freelance writer with a cute Manhattan apartment and a habit of buying $500 shoes? In real life she would be sharing a run-down flat in Queens with six other people, wearing cheap sneakers from the dollar store and eating macaroni and cheese from a box.

The show is pure fantasy, although it is a good one, but Chicago may be a little more realistic for ladies who want to live that glamorous lifestyle. There are plenty of trendy places where it’s possible to enjoy those cosmo drinks with your best friends, and enjoy the best ladies’ day out ever. And despite the breeze that comes off the lake, the city is famous for its elegant rooftop bars.

A cocktail should never be just a cocktail, and at Upstairs at The Gwen, the cocktail menu is inspired by some of the city’s finest art. It’s the perfect destination after spending an afternoon at the Chicago Institute of Art! Thanks to mixologist Freddie Sarkis, your afternoon in Chicago can start with looking at Picasso, and end with drinking Picasso. The “Chicago Picasso,” that is, a wonderful drink that includes amontillado sherry in a smoked glass.

The Chicago Picasso, an art-inspired cocktail from Upstairs at the Gwen

The upstairs, outdoor venue has a tremendous cityscape view, and The Gwen itself is located in the McGraw-Hill building, an architectural delight with Art Deco styling which preserves much of the history of the building.

And speaking of the Chicago Institute of Art, one of the best places for a short-term rental is at the Manilow Suites North Harbor Tower, right on the lake, close to the museum and only a short walk to Navy Pier. A winner of this year’s HotelsCombined Award of Recognition for the best big city hotel in Illinois, Manilow is right in the heart of the action.

If you love rooftop restaurants – and the weather is right — Right by Lake Michigan, Cindy’s has a wonderful rooftop venue on top of the historic Chicago Athletic Association hotel with a great view of the lake and Millennium Park. It’s a glass-enclosed space that looks like a Great Lakes beach house with casual picnic-style seating. The bar program, under the creative guidance of Spirit Guide Nandini Khaund, offers potions and elixirs, whimsical cocktails that are inspired by travel, science, and classic apothecary.

Cindy’s, where you can find some of the city’s most creative cocktails


Some of the more creative concoctions are the Reanimator, which is an inky black drink that uses activated charcoal (it tastes better than it sounds!), and the Foot in Mouth, a nod to the Caribbean roots of rhum Agricole. It includes “sugarfoot syrup,” which is devised of a heritage pig hoof. Let your friends try it before you tell them what’s in it! It’s a wonderful and tasty delight, and Cindy’s has so many other wonders to sample, you’ll need to come back to try everything on the menu. A must-have is the “Kick in the Daisy” margarita.

Chicago’s only Japanese rooftop bar is Noyane, which just opened in May. Noyane, which means “hidden roof” in Japanese, is on top of the Conrad Chicago, and the drink to try there is the delicious Lychee Martini. The cocktail menu there is inspired by cocktails that you might typically find in a Japanese karaoke bar. The Lynchee Martini features an edible flower garnish, and is made with Tito’s vodka, Carpano Bianco, and Giffard lychee liqueur.

Noyane’s famous Lychee martini

The seasonal rooftop destination is as serene as you would imagine, and features a central bar with a retractable roof, a sculptural fire feature, and a bar-height fire pit table that’s just perfect if the weather is starting to get a little cool.

If you’ve ever wanted to eat a butterfly, Chicago’s Apogee, located on the rooftop of the boutique dana hotel and spa is the place to do it. This rooftop bar has the most ornate cocktails in the city, with some of the most exciting garnishes you’ll ever see – including the edible butterfly that decorates the Nymph cocktail.

The Nymph cocktail at Apogee, at Chicago’s dana hotel and spa

Bring your smartphones with you, each drink is definitely worthy of a photo or two.

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