One of the questions I get most often these days is “how do I book a cheap flight from a to b?” It’s an interesting question and one that I typically can’t answer. I wish the answer was simple. I wish I could simply say “book on Tuesday” or “book 3 weeks before your scheduled departure,” but I can’t. I’ve booked inexpensive flights 6 or 7 months before traveling and I’ve booked cheap flights the day before traveling. Every situation is unique, but hopefully this example will help you understand the methods I use to book cheap flights.
Traveling From Chicago To Denver For Labor Day
Labor Day weekend is less than two weeks away and I need to be in Denver that weekend for a wedding. I’ve known about this wedding for several months (as you typically do), but I’ve avoided booking until today for a few reasons.
First, I know what you’re thinking, “for a busy travel weekend, like Labor Day, it’s best to book several weeks or months in advance.” That logic is absolutely wrong! The airlines know demand for a holiday weekend is high. As a result, the airlines set high initial prices for high demand routes and times. Sure enough, that’s what they did for the Chicago to Denver route during Labor Day. Flights from Chicago to Denver on American cost well over $300 for the holiday weekend.
I’m fairly familiar with this route since it routinely comes up as a decent mileage run opportunity. In months past I’ve typically found prices of $200 or less for a weekend round trip. That number became my benchmark for getting a good deal for my Labor Day Weekend flights. Since I now had a goal in mind I decided to wait for prices to fall before booking. For months I watched prices move up and down slightly. At one point round trip prices for economy hit $400.
I started to wonder if I’d ever find a $200 round trip on American for the Labor Day Weekend wedding. At one point I even contemplated booking a first class ticket for $500 since at least I’d get a big seat and a few beers. In the end, I continued to wait until just a few weeks before Labor Day to book these flights.
Checking Prices Three Weeks Before Traveling
In the months leading up to Labor Day Weekend round trip prices from Chicago to Denver on American ranged between $300 and $400. Then, about 3 weeks prior to the Friday of Labor Day Weekend, things started to get interesting. The round trip price for the flights I wanted dropped to $264! Since I’d been watching prices stay above $300 for weeks I immediately tried to book. Then at the last-minute I instead decided to put the itinerary on hold. Something just didn’t feel right. I figured I could get an even lower price. Sure this is a fairly bold strategy, but a risk I’m willing to take to save a few bucks.
Buying American Airlines Gift Cards For American Express Airline Credit
Three weeks before my scheduled departure date I remembered I still hadn’t used my Airline of Choice credits from my American Express Platinum card. I quickly decided to purchase two $100 American Airlines gift card to earn the $200 of credits owed. Within 48 hours the airline of choice credits posted and I now had $200 of AA gift cards to help offset the final price of my flights to Denver. Keep in mind Gift Cards typically take 48-72 hours to use once purchased. With that hold period in mind I figured I’d wait at least a week before trying to book again.
I purchased the gift cards as an insurance policy. The $200 in gift cards would reduce my out of pocket total significantly if prices jumped back above $400. Since I now had the gift cards in hand (my inbox), I had a safety net just in case prices moved significantly in the days leading up to my departure to Denver. Obviously I’ve already spent this $200 on my Amex Platinum annual fee, but mentally these gift cards help put my mind at ease.
Booking Two Weeks Before Labor Day Weekend
Finally, this morning I once again began my day as I always do. I woke up, had a cup of coffee, and began looking at Google Flights. Then I found it, the price I’ve been searching for. The price for the flights I wanted finally dropped to $218! Without a second thought I clicked through to American’s website, applied my gift cards, and booked. In total the “out of pocket” cost of my Labor Day Weekend flights to Denver is just $18. Waiting this long to book was a huge risk, but in the end it worked out, as it almost always does.
I just checked the prices again and the price is once again up to $315 ($365 for the flights I booked). Clearly in the end my plan worked and I saved nearly $100 by waiting to book at what I believe is just the right time. That being said, who knows if the price will drop even lower in the future, but I’m happy with the price I paid for my flights.
Final Thoughts
I’m glad I waited to book this trip. In the end I saved about $100 from when I first started looking at flights nearly four months ago. Over the years I’ve used this strategy time and time again. I can’t remember a time this plan failed me. If it has I’ve chosen to forget about it…
In some cases it means booking just a few days before my departure, in others two to three weeks before. In the end, for this to work you have to check prices frequently. Potentially it means checking prices several times a day or setting price alerts on google flights. Obviously this strategy isn’t for everyone, but if you and your travel companions are flexible it’s the best way I know to save money when traveling.
