1,750 Miles To Chicago From the Caribbean Racing Severe Storms

Our Caribbean adventure comes to an end with one of the longest flying days we've ever had. The plan sounded simple: depart Turks & Caicos, clear U.S. Customs in Jacksonville, and continue home to Chicago. Instead, we spent the day racing severe weather, waiting out thunderstorms at an FBO, making major deviations around storm systems, and ultimately arriving back in Chicago nearly four hours later than planned after flying more than 1,750 miles. Along the way, we were treated to some incredible moments—including a stunning Caribbean departure, special routing over the Daytona 500, and an unforgettable flyby of the U.S. Air Force Thunderbirds. What started as a routine trip home turned into an unforgettable final day of our Caribbean adventure. 0:00 Departure from Provo, Turks & Caicos 3:11 Climb & Trip Plan 10:08 Bahamas Cruise & Daytona 500 Flyover 10:58 Approach into Jacksonville to Clear Customs 17:34 Taxi & Takeoff from Jacksonville 20:14 Climbing through Storms 25:06 Descent into Chicago 29:42 Landing at Chicago Executive Connect on Instagram at / brendan.m.egan *Video for entertainment only and not designed to be an instructional or educational video. Some of the most frequently asked questions I get asked: -What kind of plane? It’s a 2024 Cirrus SR22T. It’s an Xi which is Cirrus’ custom design program, so we were able to design the paint, colors, interior and truly customize the plane to be our own! -Where are you based? Presently based at KPWK, Chicago Executive Airport, which is about 7 miles north of O’Hare in the north suburbs of Chicago. -What do you do for a living? I own multiple businesses; my main business is a digital marketing agency where we help other businesses grow through digital marketing. -Why do you fly? I got into flying primarily for business. I was sick of dealing with airlines, their schedules, terrible service and delays. I primarily travel for business however also travel for leisure to some pretty amazing places! -When did you start flying? I started flying back in 2016 in a Sundowner; however I quickly realized I very much disliked the plane and didn’t jive with my instructor. I got back into aviation in 2023 and earned my private pilot then with my instrument and commercial the year after. -What do you think is next in your aviation journey? Writing this as of 2026, I’m a little under 1,000 total hours nearly all of which are in a Cirrus. I think there is a good chance a Vision Jet, TBM or similar are in my future but for now I am loving my current plane!