By Josh March 10, 2018

For a long time, I avoided the whole world of travel hacking. I don’t know if it was the word “hacking” in the name, or if I was just OK with earning 1% cash-back or some points to spend at Best Buy (a former addiction) with all of my usual purchases. I didn’t shy away from it for the “Anti-Credit Cards” reasons that D.R. preaches, because I had already been responsibly using credit cards since 2005, when I first got out of college.

Once I made up my mind to try it, I fell down the rabbit hole. If you’re interested in starting, don’t open any cards until you’ve taken the free course at It will change your life! I also have a resources post here on the blog if you’re looking for more digestible information on some of the top cards on the market.

Once you have a stash of points burning a hole in your pocket, you might start making all sorts of travel plans. Confirmations for flights, hotels, and event tickets start to clog up your inbox. This is where TripIt can be a huge help. TripIt is a product of Concur, one of the largest travel and expense management service companies for businesses, and it feels like they’ve made this product for both leisure and business travelers.

I travel frequently for business, and I have a mixture of business and personal hotel reservations floating around in my inbox at any given time. I also get email confirmations on my parents’ travel plans, especially when they come here to Florida to visit me. Sometimes I will also reserve a hotel room *just in case* because it’s a busy time of year such as the Legislative Session in the state capital city. Once you link TripIt to your email inbox, they do all of the rest.

Take a look at the screenshot below. It shows all of my upcoming travel plans that involve a flight or an already-booked hotel and/or event ticket. The trip in September in Orlando is my first FINCON! 🙂


As you can see, I have some upcoming workshops and conferences already in my travel plans. If you click on any of the individual trips, it will show you an itinerary of all of your related travel confirmations, as shown below.


I upgraded to TripIt Pro in August 2017, and I am thankful that I did. They were running a special at the time, $34 for the first year, regular price $49. Now I receive “Go Now Alerts” which tell me when to leave for the airport, Terminal and Gate reminders (which help when traveling through an unfamiliar airport or when gates suddenly change), Check-in reminders (24 hours before on Southwest Airlines flights to get a good boarding position, amirite?), automatic trip sharing with your network that you set up in the app (great for work or for personal reasons), and best-of-all: Flight Refund Monitoring!

Last night, I received an email from TripIt at 9:18pm stating that my upcoming flight to Atlanta had decreased in price by $51, and they gave me the steps to follow to request that refund. I called Southwest and they were able to quickly make the change, and gave me a $51 flight voucher, good for one year from the purchase date of this flight. This one refund more than paid for my $34 annual fee on TripIt Pro! I’m totally sold.

In case you’re not quite sold, here’s a few more benefits:

  1. Point Tracker – once you get involved in the travel hacking game, you will have points spread across multiple hotel, airline and flexible bank point programs. This saves a lot of time spent manually tracking your various points.
  2. Seat Tracker – helps you find a better seat on flights
  3. LoungeBuddy – Comes with a free $25 airport lounge credit
  4. CLEAR – Not all airports have this service, but TripIt Pro comes with a 4 month free trial for the fastest way through airport security, even faster than TSA Pre-Check!
  1. Ah the very end of my free (won it as a prize) subscription to TripIt Pro, they alerted me to a price drop for our vacation flights. I’m trying to decide if it’s worth getting it again because we don’t travel near as often as we used to so the opportunities to make up the cost are fewer.

    1. As long as I am traveling for work, I think I will keep it, but I can certainly understand not wanting to shell out $49. Some of the features are still available with the free version, but not the flight price reduction!
      And thanks for being the FIRST EVER comment on my blog!!

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