Over the past few weeks, I’ve had quite a few questions about how I go about booking my trips, both for flights and hotels. Before I get into it, keep in mind that my big [international] trips have all been solo travel, so I haven’t had to consider additional people which could impact prices and feasibility.

Flying over Miami, Florida

Flights

Let’s face it, booking flights sucks and isn’t for the faint of heart unless you’ve got gobs of money to spend. However, for the rest of us, it usually includes a ridiculous amount of research along with the daily checking of prices.

Search All [Nearby] Airports:

When I start looking for flights, sure, I’ll look at the cost from all the airports in Montana, but I don’t hold my breath because they’re usually way more expensive than anywhere else in the country. [One day I’ll live near a major airport!] Sometimes, you get lucky though, like I did with my flight to Iceland out of Bozeman. Excluding that flight, what I’ll typically do is look for flights leaving from larger airports that are fairly easy to get to from Montana such as Salt Lake City, Denver, Minneapolis, Seattle, and even Calgary! Once I find a decent flight based on price and time frames, I usually jump on it and figure out how to get to the departing city later, whether I drive or fly. When I went to Portugal, I drove to Calgary, and when I went to Curacao, I flew to Salt Lake City.

Book Multiple Round Trips:

A little trick I learned from a friend, especially when flying to Europe, is to find the cheapest flight you can to anywhere in Europe regardless of if it’s your destination or not. Once you get to Europe, the flights are way less expensive, so you can book another round trip to your destination. I did this when flying to Portugal. My initial flight was a round trip from Calgary to London, then I had a roundtrip flight from London to Porto. Had I flown directly to Portugal, even from Calgary, I would have spent anywhere from $1,200-1,700. Instead, breaking it up into multiple roundtrips, I spent $600 for the flight from Calgary to London, and $250 for the flight from London to Porto. For those that struggle with math, I spent a total of $850 on all my flights, which ended up saving me anywhere from $350-850. I’m doing this same thing with my trip to Norway. My first roundtrip is Bozeman to Iceland, and I’ll book another Iceland to Norway. My estimated savings for this trip will be nearly $800 by choosing not to fly directly to Norway to begin with. If this isn’t a win in and of itself, I’ll also get to spend some time in Iceland, and no one’s going to complain about seeing an extra country!

Where to Search:

So, where do I search for my flights? Here’s a list of my favorite spots:

1. Google Flights
2. Skyscanner
3. Directly through the airline(s)
4. AirFare Watchdog
5. Kiwi.com
6. Momondo
7. CheapOair

Google Flights and Skyscanner are awesome when you don’t necessarily have dates set in stone as they allow you to search over time periods and generalized locations. However, for many of these, note that they are searching numerous websites for the cheapest flights. This means you may end up booking through a third-party website.

Another thing to note on most of these sites is that the cheapest price is often going to be for basic economy, so if that’s what you’re after, great! However, if you’d like to be able to select your seats and have carry-on baggage, you’ll need to upgrade to the main economy.

Hotels

Airport Hotel in Amsterdam
I’m not sure the picture does the room justice. This picture was taken through the window in the door. The room had everything you need in the smallest amount of space. The bed was built into the wall (for lack of better description), the desk folded up out of the wall, and the toilet, shower and sink all shared the same condensed space to the left (not pictured).

Now, onto where to stay. For all my international travel, I’ve booked my rooms through Booking.com and it’s been wonderful. I’ve stayed in some pretty cool places! They usually have a variety of places to stay including hostels, hotels, bed and breakfasts, and even some apartments. When looking, they advertise all prices as a total instead of a per night rate, so you know exactly what you’ll be spending. On their site, you can select specific rooms, see what’s included in the rate, and either pay right then [nonrefundable] or pay when you stay. For planning purposes, especially when you don’t have all the details entirely planned out, the free cancellation/pay when you stay option is the best! However, I should throw out that typically the rooms with free cancellation are priced slightly higher than the nonrefundable rooms.

Studio Apartment in Sintra, Portugal

Added bonuses for using booking.com:

• They have a Genius Loyalty Program, so once you book (and stay) 5 times, you unlock an extra 10% off at most of their popular properties. For me, I had my 5 bookings complete all during my stay in London and Portugal, and now I have the added benefit all the time!
• You can get rewards back for you and a friend by using referral links! If you want, you can use mine here. If you book by using this link, we each get $20 back once you complete your stay. Why not get money back?

Planning a trip of any kind really shouldn’t be such a stressor, so hopefully some of these ideas save you some time and money. It’s not full overview, but it’s a start, so if you have any questions, let me know!