Upscale Activities for Chicago Gentlemen & His Courtesan

When visiting new cities, I love to explore with a local gentleman! These are a few suggestions of luxurious activities I would love to enjoy with you in the Windy City. 


Fine Art

The Art Institute of Chicago holds the world’s largest collection of impressionist paintings outside the Louvre in Paris. Lets make it a date! The Art Institute has a variety of art mediums, audio tours, as well as accommodations such as a cafe. There’s even a direct exit to the scenic bridge that connects to millennium park. Perfect spot for views and romantic engagements!



Admiring the architecture in Chicago is a breath taking encounter all in itself. Architecture tours, or even just personal strolls in Chicago can provide a lot of inspiration and romantic vibes. If you’re a fan of architecture, let’s check out the Gold Coast! Home of multimillion dollar homes, and beautiful historical architecture, as well as the home of the original Playboy mansion! 

Speaking of scenic places to visit, not many know that the Ferris Wheel was invented in Chicago. The Ferris Wheel at Navy Pier offers romantic views of the city, especially beautiful at night with all of the city lit up. Grab a warm pretzel and drinks, and enjoy the view at the top with me! Navy Pier offers a variety of accommodations and activities, ranging from boat tours and cruise nights in the summertime to year round indoor shopping and entertainment whenever the city is chilly. 

If Navy Pier’s Ferris Wheel isn’t your thing but you’d still like to encounter the beautiful views, The Signature Room on The 95th Floor atop the John Hancock building is perfect. They have cocktail and dining accommodations to enjoy the view with while we enjoy each other. Perfect time for this kind of date is right before sunset. I’ve heard it is truly an unforgettable sight!


Sports Events 

Chicago is home of the famous Cubs team, when they are playing at home you can find them at Wrigley Field. Wrigleyville is a small neighborhood within the heart of Lakeview, infused with; sports bars, summer events and active nightlife. Additionally, if ball games aren’t your cup of tea there are several other sporting events within the beautiful city. 



Nightlife in Chicago is always popping! Prism as well as several other scenes always have something fun going on. Whether we venture out to Wicker park for casual bar outings or go to a luxurious River North club like Prism, we’re bound to have a great time. Chicago being as diverse and unique as it is there’s something for every occasion. Everything between Burlesque cabaret shows & cocktails at Bordel, comedy shows at Laugh Factory, improv at The Playground Theatre, to Hookah lounges and middle eastern dancing at Masada or Alhambra Palace, it’s all on the menu.



Of course you can’t forget shopping! From Prada to Chanel to Burberry, The Magnificent Mile has it all. There’s sure to be something for everyone ;)


Fine Dining

Chicago has several Michelin starred restaurants and other fine venues for the perfect dining experience. A few recommendations I’ve received range from the smaller but equally charming cuisines, such as the romantic French Vietnamese restaurant in Uptown, Pasteur. Or many of the surrounding cuisines from local businesses. If you’re looking for a Michelin top starred restaurant, I have been lusting after the idea of visiting Alinea by Grant Achatz. 

Let’s make memories that will last a lifetime ♡



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