As America’s third city, there is much to delight in the Windy City. Chicago originally got its name from the Native American shikaakwa – the word for spring onions or wild garlic – and although these are indeed native to the area today any visitor will be more struck by the city’s towers and buzzing day and night life.
 
The Pritzker Pavillion in Millenium Park, Chicago - Image courtesy of City of Chicago
 

With more visitors than ever, it is unsurprising there is so much to do to keep the millions who flock entertained. From exploring downtown to the Millennium Park with dramatic art works by Anish Kapoor, Jaume Plensa and Frank Gehry’s Pritzker Pavilion, there are also numerous cultural attractions, most notably the city’s vibrant nightlife and improvisation scene.
 

If comedy is your thing a must is The Second City. With regular shows at their Mainstage Theater, E.T.C Theater and Up Comedy Club, catch the freshest comedians, who follow in the footsteps of some very famous alumni, including Dan Aykroyd, the Belushis, Tina Fey, Joan Rivers and many, many more.
 
The PrivateBank Theater - Image courtesy of Broadway in Chicago
 

If you prefer a stage show with music make your way to the hit musical Hamilton at The PrivateBank Theater, though you will need a stellar concierge to manage to get tickets. If all else fails return to the comedy scene at the Apollo Theater where improv group Baby Wants Candy will be performing their improvised take on the Broadway sensation with Shamilton.
 
Dessert at Alinea - Image courtesy of Business Insider
 

For one of the best dining experiences in the city, and beyond, be sure to book Alinea, Grant Achatz’s 3-Michelin-starred restaurant which featured at number 15 on the world’s 50 best restaurant list for 2016. Choose from private dining for groups of 6 at the kitchen table, the first floor gallery’s 16-to-18 course menu, or the second floor’s 10-14 course tasting menu. After, head to the Green Mill for a nightcap and a night of jazz, from the traditional to the avant-garde.
 
Charter a yacht on Lake Michigan
 

For outdoor pursuits head to the lake in the warmer months and charter a yacht to see the city’s stunning skyline from the water, taking in the twice weekly summer fireworks to add some further sparkle. In the summer also try the Ravinia music festival in Ravinia Park which runs from June to September. Mixing classical with contemporary, last year saw Tony Bennett, Train and Yo-Yo Ma amongst many others. A walk along the lake is also a great way to spend a lazy afternoon, as is the 1,700 acre Morton Arboretum.

A trip to Chicago is not complete without art and architecture. Visit Frank Lloyd Wright’s house and studio in Oak Park or take a boat or walking tour with the Chicago Architectural Foundation. The Art Institute of Chicago could fill up many trips with its 300,000 plus art works, and just as interesting is the Museum of Contemporary Art with its sculpture garden and excellent gift shop. For something quirkier check out the International Museum of Surgical Science on N. Lake Shore Drive.
 
Museum of Contemporary Art - Image courtesy of Curbed Chicago
 

Mixing great dining, music, comedy, architecture and a stunning shoreline Chicago is a city that has lots to see and lots to do. Whatever time of year you want to visit, this is a city that will certainly keep you entertained, and entice you back for more. Book your private jet to Chicago O’Hare, Chicago Executive, or Chicago Midway International and get to the Windy City in no time.