How I Enjoyed A 2-Night Stay At A 4-Star Hotel In Downtown Philadelphia For $42

Stacks of offers knowing how to look means there are deals to be had!

Happy New Year, everyone!

I know, it's already two weeks into the year, and Larry David would be upset that I'm past the "Happy New Year" window. But here we are.

My New Year's resolution this year was to try to win back some free time. One of my biggest challenges when it comes to finding the best points redemption or travel deals is not the search for the deal itself, but rather how time-consuming it can be. While searching for solutions, I found a brand new website that takes all my credit card, airfare, and hotel rewards and finds me the best value possible. I used this on my first trip of the year, where I stayed at my first-ever Choice Hotel brand hotel in Queens, New York. The Toronto Maple Leafs had a single game scheduled on Long Island and the best value for that stop was a two-night stay for just 8,000 points per night. I used my Amex points, which transferred at a 1:1 ratio, to redeem them. I rented a car for $45 from La Guardia and paid $100 in Aeroplan taxes. Adding another $10 for gas for the car, the three-day, two-night trip cost $155. Not terrible!

The site to find those deals is Daily Drop Pro.

Recently, the annual fee renewal on my US-based Amex Gold card was coming up. I was faced with a decision. I could renew it and enjoy some of the mid-level benefits with an annual fee of $325 per year. I could cancel it, or I could upgrade to the personal platinum card, which I've had before, for an increased annual fee of $695, but with a whole bunch of added benefits that I could exploit. I had the Canadian business platinum version of this card, which I had just canceled, so having a card that would get me back into the Amex Centurion Airport lounges was attractive. But I needed additional sweeteners. Here's how I made it work.