Private Jet to Chicago, Illinois

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Buckingham Fountain is one of the largest fountains in the world, and puts on dazzling displays both during the day and at night. There are two Chicago baseball teams- the White Sox and the Cubs. The White Sox play in Comiskey Park, but the more well known and historic stadium that tourists go to is Wrigley Field, on the North Side, where the Cubs play. The NFL franchise Chicago Bears play at Soldier Field by the South Side.

Windsor Jet Management is a global leader in private jet flights all over the world, including the US, Europe, Asia, Africa, the Middle East, and all of Central and South America. With a vast fleet of private jets, Windsor is on call and ready to fly you via jet charter to Chicago.

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Things To Do On A Chicago Vacation

After arriving in Chicago via private jet charter, get into town and enjoy lodging in one of these 5 star hotels.


Chicago is known for some big buildings- Sears Tower is probably the most well known. Although now known as the Willis tower, the Sears Tower was the tallest building in the world when it was completed in 1973, and remains one of the tallest in the world today.

sears tower - larry eiring

Credit: Larry Eiring

The Navy Pier was built in 1916 and is now a popular hub of shops, restaurants, museums, movie theaters, and a 150 foot Ferris wheel. The pier is 3300 feet long and extends into Lake Michigan.


Chicago has some major sports teams in baseball, basketball, football and hockey. Arguably the most popular team is the Chicago Bulls, who play in the United Center to sellout crowds 41 times a year. If you find yourself in Chicago sometime between October and May, you should definitely check out a game. The Bulls share the United Center with NHL team the Blackhawks, who turn the court into an ice rink for hockey games.

Credit: Eric Kilby

Credit: Eric Kilby

Food & Entertainment

Chicago has a ton of great restaurants to choose from, with some great steakhouses and wine bars to choose from. Check out a great list here.

The Adler Planetarium is fun spot for families in downtown Chicago, and has 3 full size theaters, which show off remarkable displays of the sky.

Chicago is a bustling, entertaining, and happening city to explore. Make sure you arrive there in comfort and style with one of Windsor Jet’s high class and luxurious jets, and get a private jet quote today!

Airports We Fly Into:

1) Chicago Midway International Airport (MDW) 9 miles to Chicago

2) O’Hare International Airport (ORD) 19 miles to Chicago

3) Chicago Executive Airport (PWK) 27 miles to Chicago

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