Aircraft Purchasing & Sales

What's the right airplane for me? How can I tell if the price is right? What are the tax and liability concerns? How do I avoid being stuck with a lemon? What benefits / concerns are there if I lease it back to a flying club or flight school?

With more than 14 years in the business, we've helped more than 100 aircraft owners find the right answers to these questions. We work for you as consultants to help you navigate through all the issues. And when you're ready to move up to the next one, we'll help you sell the one you have.

Experts in Aircraft Purchases

If you’re one of those pilots that has always wanted to own your own airplane but never really understood how the whole thing works - look no further. We’ve played matchmaker with almost every owner and aircraft in our fleet. Most of these proud pilots learned how they could afford to own a plane by letting the club (or Windy City Charter) offset their costs through its revenue stream. The extensive records we’ve collected on over 100 managed aircraft helps us forecast revenues and expenses.

Informational Seminars

From time to time Windy City Flyers hosts seminars on this subject for small groups. We explore important topics including: forms of ownership, leaseback agreements, operational budgets, FAA compliance, maintenance and taxes. There is also the issue of new vs. used aircraft. You'll need to know where to look for aircraft, what to do about pre-purchase inspections, financing and closing. For those of you that are ready to start shopping, call the office (847) 808-1188 and ask for Dean or email us at dean@windycityflyers.com.

Buying Used Aircraft

Locating a used aircraft isn’t as difficult as it used to be thanks to the Internet, but finding the right used plane is an altogether different story. Our ability to understand the log books, recognize quality avionics and make accurate appraisals are just a few of the ways we can help you. After more than a decade in the business we've gained the experience you need to know the difference between a diamond-in-the-rough and a pig-in-lipstick. We’ll show you how to steer clear of the shady sellers and direct you towards reputable dealers instead. Most of all, we will be able to help you wade through your choices before you spend the time (and money) traveling across the country to go see them.

Leasebacks and Management

Owners of aircraft that are leased or managed by Windy City Flyers have been able to enjoy a pride in ownership, hassle-free maintenance and the benefit of a revenue stream to offset their costs. The reason we are continually adding planes to our fleet is because of the symbiotic relationship we have developed through our club members, renters and owners. As more students and pilots come in to fly with us, the need for more aircraft grows to meet the increased demand: a perfect opportunity to own your own airplane at greatly reduced costs.

Most of our owners have been able to realize significant tax deductions through a club or charter leaseback. Situations vary from person to person and there are plenty of variables and details to discuss. Even if you have determined that the aircraft you seek is for your exclusive personal or corporate use only, we are still here as a resource for you.

Corporate Aircraft

Windy City Charter offers you a special opportunity to own (or share ownership) in larger, more capable aircraft that are professionally flown. Our FAR part 135 air taxi company has been operating successfully form more than 10 years.