I love booking travel – miles and points have helped our family travel in ways that we would have never been able to do otherwise. Starting off with my very first trip booked with miles and points, we’ve gone all across the country and even to various countries across the world. I am usually the one in our family that books the travel, and while I have a pretty good record of getting it right, I do manage to screw it up occasionally.
Booking a college trip
I love to use Award Wallet to track not only my miles and points balance (like when I found an extra 159,000 Hilton points the other day) but also my trips. I like it because it gives me one place where I can see all of my trips. That lets me make sure there isn’t anything going on and also lets me
One of my kids is off at college and I had booked a trip for him to come home for Christmas. I used 21,000 Delta points one way and 16,000 Southwest points to fly back in January. I even thought to set myself weekly reminders to check on the flight prices since I could cancel and rebook the flights if the price went down
(SEE ALSO: The Southwest Cancellation Policy Helped My Family Book a Free Flight)
(SEE ALSO: The One Time I Was Happy My Flight Was Cancelled)
I’ve been checking on both of those flights for probably 2 months now. As you might expect for flights around the holidays, the price has NOT gone down 🙂
But this morning as I was checking Award Wallet I noticed that the return trip was listed in my Trips section, but the outbound Delta trip in December was not. I wasn’t initially concerned, since many times I forget to load the trips. Sometimes AwardWallet will automatically add reservations from my email, but it doesn’t catch 100% of them.
So I looked through my emails, and my online Delta account and… I couldn’t find the reservation. I’m not sure what happened but it looks like I never ACTUALLY booked the flight! I’m going to check with my son when he wakes up to see if he has any record of it but otherwise I will have to rebook it (at a now higher price). Looking at Delta, the flight is now 26,000 Delta miles, so it will cost me a few extra thousand SkyMiles.
(Almost) screwing up the dates on a flight
But wait… there’s more!
We went to Hawaii awhile ago thanks to the Turkish Airlines 7,500 miles sweet spot to Hawaii. This was one of my COVID-cancelled trips and we went at the end of February. We flew into Maui (OGG) and flew out of Honolulu (HNL). It had always been my plan to just book a cheap Southwest intra-island flight – they run several per day
But because I had February on my mind as when we’re going, I initially tried to book it for FEBRUARY 4th, even though we actually need to fly on MARCH 4th. Thankfully, I caught that before I actually made the booking. Even this mistake wouldn’t have been that big of a deal thanks to the amazing Southwest Airlines cancellation policy.
The Bottom Line
Sadly, this isn’t the first time that I’ve screwed up a travel booking.
(SEE ALSO: The worst feeling in the world: Screwing up a travel booking)
(SEE ALSO: The HUGE mistake I made by not booking my hotel early)
Aaaaand it probably won’t be the last one. At least in this case, I was able to immediately fix one mistake (well, catch my mistake before it became a problem) and one of the beauties of having a bunch of miles and points is that the other one is fixable too.
What about you? Do you have any memorable travel booking screwups? Share them in the comments
Featured post image from Justin Jackson on FlickrÂ
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Dan Miller travels with his wife and 6 (SIX!) children. He loves to help families travel for free / cheap, especially larger families. If you are looking for help, drop him an email at 
Only mistake I made was getting to the airport way too early for our flight going home . I had forgotten about it getting changed… Two less hours at Disney…