How A Travel Blogger Flew From Miami To Chicago On A Gulfstream 5 Private Jet For Free, No B.S.

The world of travel hacking fascinates me: You churn a bunch of miles using credit cards points and traveling. The more strategic you are at seeking out great deals, the more you reap in terms of benefits. Travel blogger Sam Huang over at Top Miles is very good at that, often time figuring out how to take flights that would normally cost thousands of dollars for pennies, if at all.

In his most recently adventure, he figured out how to use his airline status to book a private flight on a G5 Gulfstream jet from Miami to Chicago. Here’s how he did it…

A few weeks back, JetSmarter, a startup that bills itself as an Uber of private jet charters, briefly offered a status match for frequent fliers with over 1,000,000 miles or hold top tier elite status.

Those who qualified would receive complimentary Simple Membership for three months, which allowed you to book two seats on any empty leg flight (Jet Deals) or a seat on a certain regularly scheduled private charters (Jet Shuttles).

He just needed to prove that he was a million-miler in terms of credit card points or status. The total acquisition cost of that many miles to receive said flight? I don’t know. He doesn’t reveal how much he’s spent to be in million points club.

Thanks to the promo,  Jetsmarter eventually said “sure, come on in…” for his free membership. Once in the program, he ended up using an app called Jet Shuttle to fly him from Miami to Chicago on a Gulfstream G5 owned by the Bank of Utah.

Go read the whole breakdown of how he did it on his website, Top Miles. In the meantime, he got to take one of those totally-smug “I’m-living-the-rich-dude-dream-even-though-I’m-not-rich” pics we all dream of taking. Good for him.

Brandon Wenerd avatar
BroBible's publisher and a founding partner, circa 2009. Brandon is based in Los Angeles, where he oversees BroBible's partnership team and other business development activities. He still loves to write and create content, including subjects related to internet culture, food, live music, Phish, the Grateful Dead, Philly sports, and adventures of all kinds. Email: