Eight hours, three airlines: Getting to Iceland

In March, my friend Ben texted me to ask if I would be interested in going on a trip in early May. We immediately started throwing around ideas, but didn’t really land on anything. “What do you think about Iceland?” Ben asked 10 days before our trip. We kicked around the idea for another two days, debating the weather, before we bought our tickets. 
Round trip tickets from Houston to Keflavík typically go from $750-$1100 on traditional airlines. With the short notice, they were all on the higher end of the spectrum, and there was nothing that fit my schedule. 
I had to present at a meeting all morning on the day before I wanted to get to Iceland. The meeting was held at a hotel in Galveston, an hour away from Hobby Airport. Hobby’s not my favorite or the most popular airport in Houston, but it’s significantly closer than Bush Intercontinental. The only way to get to Iceland by Tuesday morning was to airline jump my way across the US: 

Houston —> New Orleans on Southwest Airlines
New Orleans —> New York on JetBlue
New York —> Keflavík on WOW Air

​My first flight from Houston was scheduled to land in New Orleans at 6:15 pm and boarding was set to close on my flight to New York at 6:30 pm. Obviously I was super nervous. There was an identical flight leaving Houston an hour earlier than the one I’d booked, and I called the night before to make sure there were seats open on the off chance I made it to the airport early. I rushed through my meeting, changed out of my business casual clothes in the bathroom of the hotel and hopped in my car.
Luckily, I made it to the airport with time to spare, so I called Southwest from the parking lot and changed my ticket. The difference was about $100, which is a lot less than I would've had to spend if I had missed my flight to New York. It turned out to be a really good move because I had to leave the terminal and go through security again in New Orleans to get on my JetBlue flight to JFK. 
Once I got to New York I had to leave the terminal and go through security one more time before I could get on my WOW Air flight to Keflavík. The airline is so small it isn’t even labeled on airport signs, and security didn’t recognize the name. A quick Google search told me it was in Terminal 1, a hodgepodge of cheaper, internationally-based airlines. I had the whole row to myself and slept through the entire five + hour flight. Through WOW Air, I paid $360 including taxes and fees for a roundtrip flight from New York to Keflavík. The fare probably would’ve saved me a ton if my schedule beforehand had been more flexible. As it was, this was not at all the cheapest route to Iceland, but I got there by Tuesday morning well rested and ready to start the day. 

tl;dr

If you’re forced to piece together an itinerary with multiple airlines, make sure to leave plenty of time between your flights. ​