How Freebird Saved My Bachelor Party

April 20, 2018

I almost never buy trip insurance. I have a credit card that offers some travel benefits that help me get refunds during flight cancellations. But in November 2017, I booked a flight for February to my bachelor party in New Orleans, and I started to think that this could be the perfect opportunity to try out the new “Freebird” service I had heard so much about. I was worried about the risk of flying out of Boston in mid-January and this was not an event that I could afford to miss! So, I went to Freebird’s website ( and purchased coverage for my itinerary.

Fast forward to February, and the weekend of my bachelor party finally arrived. Honestly, I had totally forgotten that I had purchased Freebird coverage, but it turned out to be a very fortuitous decision. I was scheduled to leave around 2pm on a Friday, and my plan was to arrive at the airport by noon. Even though there were reports of heavy snow arriving in Boston that evening, no flight delays had been announced.

In the middle of my 9am Friday meeting, my phone buzzed with a personalized text from Freebird. “Hi Ananth, Freebird here! We see that your flight today has been delayed over an hour. We’ll continue to monitor your itinerary, and if the delay exceeds 4 hours we’ll rebook you on a flight of your choosing!” This was the first I had heard of any flight delay. I couldn’t believe I had been alerted by Freebird  before hearing from my airline!! Sure enough, when I checked the Spirit website my flight had been pushed back by an hour. Freebird continued to text me as the delay on my flight grew significantly. Finally, the delay exceeded four hours, and I immediately received options to book a new flight directly on my phone. Hani, the support representative handling my situation, introduced himself and let me know he’d do his best to get me to NOLA with as little delay as possible when I told him about my bachelor party weekend plans.

Within 15 minutes, he had already sent me multiple flight options on several airlines– there were no direct flights available, but he saw flights connecting through Atlanta, Chicago, Philadelphia, Dallas… all he needed was my approval and he could get me booked. When I left my meeting about half an hour later, most of the original Freebird options had sold out. I spoke with Hani personally on the phone, and he told me to head directly to the airport while he researched additional options.

Sure enough, by the time I arrived at the airport Hani had three different flights on three different airlines reserved and ready for me to choose from. I picked a Southwest Airlines flight going through Nashville because it was the farthest away from the storm and had the shortest layover — I’d still be able to make it to New Orleans by 9pm that night. The rebooking process was quick and easy and I had a new ticket within a few minutes. I felt even better about purchasing Freebird when I found out my initial itinerary had been canceled altogether as I was going through security.

Once I was at the gate, I messaged my friends to let them know that my original flight had been canceled but I would be arriving a few hours later. They immediately started offering to cover the change fee and new tickets cost for my flight… they were amazed when I told them it hadn’t cost me anything because I was covered by Freebird! I boarded the plane, had an in-flight beer, and settled into a nap to rest up for the big weekend ahead. As I woke up upon descent into Nashville, I received notifications that my connecting flight had ALSO been canceled due to “unforeseen weather conditions.” I looked out the window and saw snow on the runways. I thought I was going to be stranded in Nashville!

Upon exiting the plane, the airport was in total chaos. The blizzard had suddenly hit Nashville while we were in flight, and nearly all outbound flights had been canceled. Every gate agent was dealing with long lines of confused and angry customers, and nobody had any idea when things would be back to normal. I tried my luck with a  Southwest rep, only to learn that he next flight to New Orleans wouldn’t depart until 9am the next morning, didn’t have any available seats, and would probably be canceled anyway. At this point things looked pretty dire. I had no idea what to do and started to grapple with the possibility that I’d be spending my bachelor party weekend alone in Nashville.

I updated my anxious friends in New Orleans, and my stomach continued to sink. I felt I’d never reach my destination. Fortunately, my decision to purchase Freebird continued to pay off!, Hani was right there with me, messaging me that he had other options that were available. Hani quickly found an alternate route for me that got me into New Orleans early the next morning. When I arrived, my friends and I had an incredible weekend.

Overall, Freebird seriously saved me from a travel nightmare and turned what could have easily been a total disaster into a great experience. The service was so personal and helpful that I’ll be providing it to all my wedding guests! Thanks, Freebird!