How to Find the Best Flight Deals

Without jumping through reward hoops

For someone who travels relatively often, I’m remarkably bad at navigating travel rewards and points. I hate having to transfer points to partners or managing categories to maximize the return. Could I be saving a ton of money? Probably. But, I’m too lazy and I just want it to be simple.

Instead, I try to find the best deals possible without giving me a headache. And use my credit card points as a statement credit to reimburse my travel costs.

Here’s how I find a good deal without going crazy:

Stay Flexible

This is one of the best ways to save a buck on travel. Last minute deals, mid-week flights, and off-peak travel opens so many cost saving opportunities. However, I know not everyone has the flexibility in their work schedule to make this happen.

There’s a whole science to maximizing your PTO days, but holiday travel also tends to be pricier. If you can swing it, look for dates before or after holidays. Be open to traveling in shoulder seasons (more on that below) and be as flexible with dates as possible.

I use Google’s Explore feature to find the cheapest combination of dates within a set timeframe I know I’ll be able to travel.

Remember, flexibility applies to your destination, too. Consider going to a lesser traveled city or region. You’ll skip the tourist-y traps and save on a more local experience.

Try a Shoulder Season

Traveling in shoulder seasons (typically Spring or Fall) can save you hundreds without sacrificing the weather or activities you’re looking for. Find the most popular time of year for travel to your destination and go a month or so before or after.

Take Italy for example. It’s packed with tourists in the summer. It’s crowded and hot and expensive. But, the average temperature of the Amalfi coast is still 80°F in September. You can save on flights, hotels, and crowds by delaying your trip a few weeks. Very much worth it in my opinion.

So far, the cheapest month I’ve found for flights is January. No one seems to want to travel post-holidays, so it could be your opportunity to save.

Know When to Book

You can find all sorts of tips to try to game the algorithm. Only book on Tuesdays. Search incognito. While these sometimes work for me, I’ve found that it’s better to plan early and keep an eye on prices.

Google flights has a few handy features when it comes to price tracking. You can sign up for notifications when the price changes. Or, you can look at the price gauge to see it it’s a low, typical, or high price. The price grid helps you find the cheapest combination of days. And sometimes there’s a note about how far in advance to book to get the best deal.

Other flight search apps like Skyscanner or Hopper offer the same thing. I typically track the price with Google and Hopper. Usually, the prices are the same, but sometimes there’s a discrepancy you can take advantage of.

I also tend to book through the Capital One Travel Portal with my Capital One card (I know, I could probably save more transferring points). They also offer price tracking and if they tell you to book, you’ll be refunded the difference if the price drops again.

Act Fast

If you see a good deal, go for it. Could you save $15 by waiting? Maybe, but it’s far more likely to go up in price than down. For me, anything under $500 to Europe and under $300 domestically should be considered (depending on the destination—I would never spend $300 to fly to Florida).

I love travel newsletters like Pomelo that combine all these tips. They send daily flight deals to places all over the world. If you have a paid subscription, the deals are tailored to your home airport. If you can be flexible in dates, destination, and book fast, this is really the best way to save a ton of money on flights. I also use Pomelo for general travel inspo.

Switch Positions

My home airport isn’t a major hub. Almost every destination requires a layover and prices reflect that. However, I can easily drive to Toronto or take a less than hour flight to NYC. Especially for international travel, check out flights from major airports. Then, book yourself a cheap flight to that city or drive if it’s close enough.

A little extra travel time and the energy to coordinate your own itinerary could save you hundreds. Don’t be afraid to look outside your home airport.

Case-in-point: We flew to Dublin from Toronto in September 2023 for $497 each, and with my credit card points, it came to just $225 each. Even with offsite parking costs, we saved almost $200 each by flying from Toronto.

I booked my first flight of 2025 for a birthday trip to the Rocky Mountains this summer. I’ve also got my eye on a long weekend trip this spring (please send recommendations), a late summer adventure in Nova Scotia, and I’ll be in Mexico for work at the end of this month. Where are you headed this year? I hope you got a great deal.