Part 2: Swept Away in the Windy City

Part 2: Swept Away in the Windy City

Chicago feels truly cosmopolitan. In some ways, like being back in Athens. The locals are impeccably dressed (a BIG plus in our book!) and you get the notion that they're really, really living. The city streets are vital and alive late into the night, the restaurants are crowded, the sky bars across the city are raging and the cocktails are flowing. Summer is in full swing. As is always the case - there was much to see, and not enough time! We hope our favorite picks serve as ideas for planning your next great adventure...



Chicago is known for deep-dish pizza. And we almost had deep-dish, before happening upon something just a little more delicious – that's right... MORE DELICIOUS. We spent our first evening at Ristorante Quartino a local pizzeria and wine bar. We ordered a D’Anitra pizza (think: thin crust, duck prosciutto, onions and wild arugula) and Beef Filets with broccoli rabe. I’m sorry, are we making your mouth water?! Oh...


Small, simple and tasteful. Enolo wine bar could easily be classified as every urban fashionistas watering hole. Enolo boasts a 25 bottle wine list featuring a wide selection of wines including some that are exclusively sourced from micro vineyards worldwide. The ambiance is elegant with crystal chandeliers, patterned black walls and a grand gold ceiling and bar. On a side note salads were fabulous! 


Dreamy PB&J macaroon from Alliance Patisserie


Can you say gluten free crepes with fresh berries, bananas and walnuts? Oh don’t forget the side of whipped cream. This chic spot is an extension of the Dana Hotel and Spa but definitely can stand on its own. Tastefully decorated with an indoor space and a quaint outdoor patio Freestyle food+drink is the perfect spot to brunch with your soul sisters. And for a woman who likes bubbles with her breakfast – there were four different variations of mimosas. 


Every fashion forward woman knows that good fashion is always accompanied by chic fare and there is no fairer food then the French macaroon. Where can you get this sweet treat? Alliance Patisserie is our pick! The flavors range from traditional pistachio, Madagascar vanilla and raspberry to contemporary, peanut butter & jelly, strawberry shortcake and lemon poppy. French trained Executive Pastry Chef Peter Rios gives us something sweet to dream about long after we've savored it!


Panoramic views from our balcony at the Dana Hotel & Spa



On this trip, we can only really report on one place to stay and it sure as hell got our stamp of approval. The Dana Hotel and Spa is as fabulous as you would expect a boutique hotel in downtown Chicago to be. It is modern, avant garde, and trendy. The rooms are comfortable and minimalist with panoramic views of downtown. The hotel also boasts a day spa that offers a wide variety of massages, skin care and full body treatments and nail care.  All in all it is a fashionista’s dream spot for rest and relaxation. And it's just down the street from a Pure Barre studio and Fly Wheel! Amen.





Located on the 18th floor of the Raffaello hotel, Drumbar is a speakeasy-esque rooftop bar located in Chicago’s Gold Coast neighborhood. Cocktail focused, this bar will make you want to let down your hair and have just one more! The bar not only has a prohibition era intimate indoor space, with low lighting and leather couches right out of the roaring 20s but an exotic outdoor terrace with a views of the Hancock building and lake Michigan. Girls who like bubbles – there is a wide selection available on the bar menu. Women who like cocktails, do yourselves a favor and try the Sunset Tan -- it has enough Gay Black Barrel Rum, Pineapple Gum and Tawny Port to start any party. 


This bar was created to set standards. Located on the 26th floor of the Dana Hotel and Spa, Vertigo Lounge and Sky Bar is setting the bar high – 26 stories high to be exact. Maybe it is the crystal clear view of the entire Chicago skyline, the modern and state of the art furnishings or the custom crafted cocktails in the indoor lounge area. Or perhaps it's the fire pit, lamps and plush robes offered on the outdoor patio. Whatever IT is, the Vertigo Lounge and Sky Bar makes all cares drift away. It's just that fabulous.


If you're short on time, but want to squeeze in a little sightseeing, set Cloud Gate (better known as The Bean) as your destination. This mirrored sculpture in Millennium Park will have you stretching, bending, stooping, twisting and turning - all in pursuit of the perfect selfie!