With soaring skyscrapers, a world-class restaurant scene and internationally-renowned culture, you could be forgiven for thinking you’re in New York.
Chicago certainly has all the big city glamour and grandeur of the Big Apple but boasts a more laid-back ambience with plenty of outdoor attractions and a beach-fringed lake for swimming, fishing and paddleboarding.
When your private jet charter touches down in Chicago O’Hare International Airport, it’s just a 16-mile drive into the city.
Try the luxurious Peninsula Hotel, just off Chicago’s Magic Mile, which boasts a rooftop bar, exceptional Chinese food and a ‘spa’ button in the bathrooms which softens the lighting, plays a soundtrack and activates the ‘do not disturb’ sign on the door.
For a hipper boutique stay, try Soho House – the Chicago outpost of the globe-conquering English brand.The hotel and private club boasts a heated rooftop pool, boxing ring, 30-seat cinema and four restaurants.
For foodies, the Thompson Chicago is a treat as it boasts Nico Osteria, the hottest restaurant in the city.
In the Gold Coast area of town, packed full of excellent places to eat, the hotel has floor-to-ceiling windows to show off stunning views of the city skyline, the popular cocktail bar Salone Nico and a luxury car service for guests.
To enjoy a cocktail or two when you’ve relaxed after your private jet charter, sink into a chair by the fireplace at Scofflaw, a gin-based bar that also has plenty of unusual ingredients on the menu such as zucca (a rhubarb aperitif) and baijui (a pineapple-flavoured spirit from China).
While out on the town, you can try to solve the eternal question – does Chicago or New York have the best pizza? Locals are proud of their deep dish version, so tuck into a slice or two at Pequod’s Pizza.
Or for a more upscale experience, try Maple & Ash for seafood, a martini lounge and some of the best steak in the city.
For a Michelin-starred 13-course tasting menu, try Kasama. The venue transforms from a casual daytime brunch joint to a smarter venue in the evening, with dishes with a Filipino twist including wagyu beef and a croissant with black truffle shavings.
As well as the city’s thriving food scene, it’s also renowned for its art – both indoors at the Art Institute of Chicago and outdoors with Anish Kapoor’s world-famous reflective bean sculpture, Cloud Gate.
There are also plenty of museums and attractions. You can see a beluga whale at the city’s huge Shedd Aquarium in the morning and gaze at a skeleton of a T-Rex at the Field Museum in the afternoon, or if the sun is out, catch a Cubs game at Wrigley Field and an architecture cruise down the Chicago River.
Chicago winters are relentless (it’s not called the Windy City for nothing) and the height of summer has soaring temperatures but in the warmer months of April/May and September/October private charter flight visitors can enjoy the best of the city’s outdoors attractions.
Chicago may have the best of New York, but it has a story and attitude all of its own.
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