ATC Said We’d Never Get Into Oshkosh… We Did

We were determined to make it to EAA AirVenture Oshkosh, but Canadian wildfire smoke had reduced visibility at KOSH to just one mile—turning our planned VFR flight on the Fisk Arrival into an IFR operation. Our IFR flight plan from Chicago Executive was rejected because we didn’t have an arrival reservation, so we departed KPWK VFR and tried to find another way in. Chicago Approach warned us there was almost no chance of getting a popup IFR clearance into Oshkosh, and Allison was convinced we would be spending the weekend somewhere else. I promised her I would find a way, despite having no real plan beyond begging ATC. When we reached Milwaukee Approach, we tried one more time—and somehow received a popup IFR clearance. We were vectored onto the RNAV Runway 27 approach, descended through the wildfire smoke, and landed at the world’s greatest aviation celebration. Come along for the flight, the smoky IFR approach into Oshkosh, and an incredible few days at EAA AirVenture. Connect on Instagram at / brendan.m.egan 0:00 Departure from Chicago Executive KPWK 3:55 Takeoff & Climb 7:40 Getting Denied Again To Oshkosh - Discussing Alternatives 12:04 Miracles Do Happen 17:28 RNAV 27 KOSH 22:12 Welcome To Oshkosh *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!