Nov. 23, 2022

Booking Flights with Points and All Things Award Travel

#89: Award travel pro Tiffany Funk joins Chris to talk about booking flights with miles, the advantages of having travel flexibility, the ins and outs of transferring points, ways to put your points and miles to good use, and the best sites/tools for booking award travel.

Tiffany Funk (@tebfunk) is the co-founder and president of, a one-stop tool for maximizing points and miles. She's also the Executive Director for the premium travel site One Mile at a Time. Having visited over 80 countries and written more than 300 travel blog posts, Tiffany ​​is one of the world’s top experts on airline award travel and loves sharing her passion with travelers on frequent flyer programs, earning and redeeming miles, and maximizing points.


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Selected Links From The Episode

Connect with Tiffany Funk: Twitter | Website | LinkedIn

One Mile at a time (first month for $1 with code ALLTHEHACKS)

Expert Flyer


Google Flights

Loyalty Programs


Full Show Notes

Introduction to Tiffany Funk  (00:00)

Award flights vs. redeeming points for cash back (01:31)

General guideline to aim for when redeeming points through loyalty programs as opposed to a credit card portal (03:47)

Determining the best value of your points (05:44)

Tips for using points to purchase multiple tickets (09:12)

Transferring points: where to start (15:18)

Flexible points (20:46)

The sweet spot for when to book a trip (25:01)

The best use of points when you have flexibility (26:55)

Things you can do with miles that you can’t do with money (27:58)

Advantages of having a destination, itinerary, or dates that are flexible (29:19)  

Amazing trips with better availability for someone with points (33:30)

Using points on airlines vs. hotels (39:06)

Why technology has made it difficult for people to use points for flights, and what to expect in the future (43:32)

The secret to’s success (45:33)

How works (51:09)

How to save money on your first month of membership (53:46)

Chris’s airline search advice (55:04)

Listener suggestion: find flights using (56:08)

Tiffany’s tool recommendations for reward travel (58:12)

Married segment itineraries (59:47)

How to get a good sense of how much a trip may cost (1:01:35)

Hacks to reach your mileage goals (1:03:30)

Chris addresses the issue of the difficulty in combining points for a trip and provides tips for getting around certain obstacles (1:06:26)

Tiffany Shares Her Opinion on the Best Use of Your Points (1:11:59)

How can teach users to build better reward travel booking skills? (1:13:11)

Tiffany’s Travel Recommendations (1:15:27)




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