Caitlin Deegan
Vice President of Sales | Tru Air Advisors
PH: (312) 792-8351 · E: caitie@truairadvisors.com
Welcome, as your dedicated charter advisor, I’m here for any private aviation need — one point of contact, not a call center. I bring the same hands-on, detail-first approach that defines how Tru Air Advisors works: full transparency, a straight answer, a fair price, and a trip planned like it’s my own. From your first request to wheels down, I’m the one handling every detail, so you always know exactly where things stand.
First Time Here? Let’s fix that. Learn More About Me
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Let’s Plan Your Trip
Tell me about your trip, and I’ll take it from there. Where you’re going, when, and how many — a few details is all I need to get started.
Rather Watch Than Read?
The Briefing
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Get the One-Ways in Your Inbox
Join my One-Ways list and I’ll send you a short roundup of available repositioning flights every couple of weeks. Private jets already heading somewhere, often at a discount to standard charter. Better yet, tell me where you’d love to go — there’s no shortage of these flights. The hard part is matching the right one to the right person at the right time, and that’s what I’m here for.
Let’s Plan Your Trip
Request a Quote
Tell me about your trip, and I’ll take it from there. Where you’re going, when, and how many — a few details is all I need to get started.
More About Caitlin
How I Work With You
A Bit About Me
With 20 years of experience in aviation and charter, I bring seasoned insight and a client-focused mindset to Tru Air Advisors. My aviation career began in Los Angeles at a renowned operator, where I spent five years in customer service while supporting the charter department — laying the foundation for my expertise in high-touch, high-stakes client relations.
I continued pursuing my passion for aviation by joining a worldwide aviation consultancy, where I spent 14 years refining my craft. My bespoke service approach, deep operational understanding, and ability to build lasting trust allowed me to serve elite clientele across major international markets including London, New York, and other global hubs. During this time, I also mastered the art of arranging flights for major music tours and A-list movie productions, managing complex logistics with precision and discretion.
My success in cultivating long-term relationships and growing new business ultimately led me to open and lead the company’s Chicago office, where I built and scaled a high-performing team from the ground up. I welcome a bit of humor and lightheartedness in what can be a complex but deeply rewarding industry — I’m fully committed to making each trip seamless, unique, efficient, and memorable.
Outside of aviation, I’m a proud Wisconsin native and lifelong Packers fan living in Chicago with my husband and our dog. I bring the same loyalty, competitiveness, and enthusiasm to my clients that a Packers fan brings to life in Bears territory.
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Things Worth Knowing
A few pieces we’ve written that answer the questions I get most.
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