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Private Aircraft Charter in Chicago Mastering All Aspects of Private Travel

Planemasters, one of the Midwest’s largest executive charter operators, can transport you to and from your destination quickly, safely, and in the comfort of our world-class aircraft. Our exceptional blend of owning and operating our own fleet of aircraft, while also being able to act as an Authorized Agent for our clients in sourcing outside aircraft for their trips.

We are committed to offering you freedom from canceled flights, inconvenient connections, and general airport chaos by providing direct access to locations around the globe.

Our dedicated, 24-hour scheduling department is available to help you choose the appropriate aircraft to meet your travel and budget needs. Whether you’re planning a corporate meeting or arranging a family getaway, we have the right aircraft for you.

Elegant man with headphones sitting inside private jet airplane and holding digital tablet

We Take Pride in Delivering More Than Just an Aircraft

We offer beautiful and luxuriously appointed aircraft, heated indoor parking, tasteful reception lounge, and a professional and skillful concierge team. These are only a few of the amenities we offer at Planemasters. Our dedication to superior service is unparalleled and has been since 1970.

Booking Private Charter

From start to finish, your private charter experience is seamless with Planemasters. Our seasoned scheduling and concierge staff will guide you through the process and take all the stress out of travel. Here’s what you can expect when booking with Planemasters.

Cabin crew of a private airplane at the airport looking at the camera smiling

Requesting a Quote

You’re going on a trip and decided to fly private, great! First things first, you reach out to Planemasters and request a quote. Someone from our scheduling team can answer any questions you may have and will email a personalized quote. We also have a helpful aircraft guide to aid in your selection.

Two adult couples sitting inside private jet airplane and enjoying their flight, cockpit is in the background

Confirming Your Trip

After receiving your quote and looking over all the details in the attached contract, you’ll return to us the signed paperwork and Planemasters will add your trip to the calendar.

Woman with credit card and laptop


There are several different options available here to help make this as convenient as possible. Full payment is required 24 hours prior to your departure.

  • Wire Transfer or ACH – This is the preferred method. All banking information and instructions will be provided and there are no additional fees associated with either method.
  • Credit Card – After providing your information, our Accounting team will run a pre-authorization for the amount. The credit card will then be charged no later than 24 hours prior to departure. There is a 4% fee associated with this method.
  • Check – Personal and cashier’s checks are both acceptable. Drop the check in the mail or feel free to stop by our office, if time allows. We’d love to see you before your trip! There is no additional fee associated with this method.
Two businessmen reading documents on private plane


Through phone calls and emails, we will work together to go over every last detail of your trip. From departure and arrival times, passenger list, catering, assistance with ground transportation, and any other special requests, we’ll cover it all. You’ll receive a finalized itinerary no later than 24 hours prior to departure.

Mature professional couple travelling by luxurious private jet

Travel Day(s)

Simply show up at the departure location. Passengers typically arrive approximately 15-30 minutes prior to take-off. There is no need to arrive hours in advance like with commercial flights. Our pilots will handle any baggage and get you on your way.

Close-up of a jet-plane parked inside a hangar

Our Guidelines

An aircraft within our fleet may be unavailable, or perhaps the client has requested an aircraft that is not operated by Planemasters. As an Authorized Agent, we have the ability to obtain the appropriate aircraft for that trip. Planemasters will only select carriers that are certified by the Federal Aviation Administration and register with the U.S. Department of Transportation. We ensure that the carrier meets or exceeds our same level of safety standards and possesses all the necessary liability insurance. Planemasters evaluates each carrier for reputation, crew experience, and third-party affiliations.

What It Means for You

The best part is there are no extra steps for you, the client. You simply need to submit your quote request, contact form, or give us a call, and Planemasters will do all the rest. Based on the information you provide, we’ll be able to present you with the best aircraft to meet your needs. You can also view our Fleet when looking into your options. This helpful breakdown will give you a better idea of the various types of aircraft with regard to their passenger capacity, flight times, and baggage volume.

Wherever You Want to Go, We’ll Take You There