Skiplagged.com. This is a new one to me and I haven’t tried it out yet. They’re in the middle of a lawsuit with Orbitz and United Airlines right now that could change the service, but for now it seems like a great way to find and setup alerts for cheap fares. In particular it seems like it could be a good tool for scouting out those cheap, one-way tickets that are generally kind of a crapshoot.
Hipmunk. Truthfully, I’m not sure their airfare search capabilities offer much more than some of the options below, but what I do think is very cool is their hotel search. I hadn’t used their site in a long time but someone recently wrote to me and pointed out that you can now search Airbnb listings alongside regular hotel listings there. Airbnb is almost always the cheapest (And most fun!) option, but there have been situations where that wasn’t always viable. It’s cool to be able to search and compare to hotels in the area.
Kayak. Not always the cheapest but a good place to establish a base price and perform your search across multiple services. It helped my find a last-minute ticket from Rio de Janeiro to New York for about $800 at about 2am after missing my earlier flight. Their Explore page is my favorite thing about them these days.
Spirit Airlines. Good for cheap, domestic flights. Their low fares come from heir draconian baggage policies but if you’re the type to avoid checking bags at all cost like me then it’s worth a look.
Ryanair. If you’re in Europe and looking cheap air to other European destinations I hear this is good. Recommended by a friend in Austria.
AirTreks. For continent-hopping and big adventures spanning many miles in a relatively short amount of time I highly recommend their service. For my year of traveling (2013) I mostly went this route buying two groups of tickets about six months apart. They took me to about 18 countries in all and nearly every continent. Twenty-plus flights came in averaging about $370 a ticket as I recall.
Airbnb. I basically lived off Airbnb for a year. It’s a really neat way to meet people who are actually from the place you’re visiting. The prices I find are generally between a hostel and a hotel but so much nicer than both off those options.
Couchsurfing. If you’re only staying somewhere a short amount of time then this can be a great option though I’m sure more adventurous people than me have leaned on it as heavily as I leaned on Airbnb. It’s also a good avenue for finding activities to do in the place you’re visiting — maybe think Meetup but with a little bit more of a travel-angle. I remember finding a some expat yoga in Sofia, Bulgaria when I was there.
See my note on Hipmunk under Airfare.
Koryo Tours. This is the tour company I went through when I participated in the Pyongyang Marathon in Spring of 2016. People ask me about this one a lot. I wrote a little bit about my adventures in North Korea and plan on writing more.
Modern-Day Nomads. Their newsletter is really fantastic. I frequently find myself taking a break to peruse the opportunities and daydream a bit.