Recently I have been planning and booking travel for a trip out to Indianapolis from Philadelphia; then from Nashville back to Philadelphia using as little money and as few points as possible. The plan was to fly out to Indianapolis from Philadelphia on Frontier airlines (get excited for that review!). The next day I’d drive with friends from Indianapolis to Nashville, stay in Nashville for a few days, then fly back on Southwest to Philadelphia.

During the process, I ran into a few snags that showed why it’s so important to diversify your points. The original plan was to use a free night certificate at the Hyatt Place in downtown Nashville and then use points for the next night. When I went to book the one night I got the dreaded, “The special offer/rate you have selected is unavailable during the dates you have selected, or it is not offered at this property.”

The worst thing to see on Hyatt’s site when trying to redeem points.

Ugh! This is the worst thing to see, but it’s my fault for taking too long to book. Luckily I have a fair amount of Hilton points and was able to book a room for one night at the Hilton Nashville Downtown and the other night at the Hyatt. So, besides remembering to book trips early, it’s also important to diversify your points so you have a backup option when things go wrong.

Southwest points

Even though I was getting two tickets for my Southwest flight from Nashville to Philadelphia, I always look up tickets for just one person. Why would I do that? Well, as I have learned, sometimes the points shown for two people are higher.

For example, if you search for two tickets on Southwest’s website for the date I needed and fly nonstop from 9:45 a.m. to 12:45 p.m. you see:

Points needed for two people

18,444 points per person for the 9:45 a.m. flight. Not the best redemption ever, but beggars can’t be choosers. Then when looking up a ticket for the same flight for one person, this was the point redemption:

Points needed for just one flier

Points needed for just one flier

All the point redemption values are the same except for the 9:45 a.m. flight! If I booked just one ticket first it would be just over 2,000 points cheaper. If I booked the tickets at the same time, Southwest doesn’t offer the one ticket at the lower value.

You have two options here. First, you can book one ticket at a time and get one for 15,757 points and the other for 18,444. Second, you can book both tickets for 18,444 each, then use Southwest’s free flight change feature to get reimbursed the 2,000 some points.

So remember, always diversify your points and when searching for flights, check for just one person then for two people and see if there are any point discrepancies.