How to find the best flight deal for your vacation

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Organizing a trip is complicated! You have to think about hotels, getting around, activities, and most importantly, flights.

Booking a trip can be particularly hard if you have specific dates in mind. While Max and I typically try to take vacations based on flight deals we get through Scott’s Cheap Flights or similar email list-servs, there are times when we have specific dates and locations that we need to be somewhere. It can be intimidating to look at the prices and decide what options are best for your needs. Here are our tips for booking those types of flights:

Google Flight Alerts

The easiest way to keep an eye on the best to buy your flight is by checking Google Flights and setting up an alert. Google Flights aggregates flights from the majority of airlines and displays them in order of price. When I start the adventure of booking flights, I always start at Google Flights.

When searching for the destination and dates, you can view a calendar that displays the best prices in green. If you have any flexibility on dates of travel, I highly recommend checking out the best days to fly.

Once you’ve locked in your dates, you’ll have the option to “track prices”. This will send you an email anytime the price changes:

Unless I see an outrageously good deal, I tend to track the prices for my dates for a week or two to see if they change at all. The best booking days that I have found are Tuesdays, Wednesdays and Thursdays. I typically avoid booking Friday-Monday as the prices tend to be a bit higher.

What to do if prices are out of your budget

Sometimes, the flights just seem outrageous (like our recent attempts to fly with cash from SFO to Curacao in the Caribbean). We couldn’t find any tickets under $900 USD, which is the same price of a ticket we found through a flight deal from SFO to the Maldives…like…seriously?? It seems outrageous to book ourselves to the Caribbean with that kind of price tag. Our next mission was checking transfer partners on AmEx points or booking using the Chase Ultimate Rewards portal with our Sapphire Reserve.

AmEx Platinum

The American Express platinum card allows you to transfer your points to partner airlines or hotels brands. Sometimes, you can get lucky and get a great deal by transferring points. For instance, transferring to Etihad or Singapore Airlines, can often get you cheaper points tickets than if you were to book elsewhere. Depending on your destination, this could be a great option if you have a chunk of points to spend. For instance, I found 35k points tickets from SFO to Singapore in Economy. Plus, with the AmEx platinum, you have access to their vast lounge network so your journey will be half of the fun. Check out our blog post here, for more information.

Chase Ultimate Rewards Portal

An option we often default to when booking flights is booking through the Chase Ultimate Rewards portal. The Chase Sapphire Reserve card makes it easy to rack up points with their 3x points per dollar on dining and travel. That means any purchase at Starbucks, airlines, hotels, parking etc gives me valuable points that sure seem to add up quick. Booking through the portal also increases the point’s value. Each 1 point is actually worth 1.5 points when you’re booking directly in the portal, giving you 25% more value. This means that if the points ticket price is 20,000, you will only be paying 15,000 points for the same booking.

I have booked many flights through Chase’s portal and have been really happy doing so. While some points fanatics will argue that you can get a better value elsewhere, the ease of booking and value you get is worth it to me. Want to learn more about the Chase Reserve? Check out our article, here.


While you sometimes have to suck it up and bite the bullet for the expensive flights, these are our favorite tips for saving some money when booking travel. Tracking the prices for cash tickets or using points can be a great way to plan your trips when you have specific dates in mind. Rest easy knowing you can enjoy the rest of your trip and save money for the fun stuff!

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