My Process for Booking Travel with Points & Miles
All the Hacks: Money, Points & Life
Upgrades Usually Aren't the Best Value
Chris Hutchins says mileage upgrades rarely pencil out and suggests alternatives for travelers whose employers only cover economy tickets.
#272: Learn how to turn your points into significantly better travel experiences by following a simple, repeatable system. We cover how to plan, find award availability, choose the right tools, and decide between portals vs. transfers, plus the mindset shifts that make the whole process work.
Link to Full Show Notes: https://chrishutchins.com/booking-travel-with-points-and-miles-2026
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Resources Mentioned
Award Search Tools
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AwardTool ($20 off annual plans with code ALLTHEHACKS)
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point.me (20% off annual plans with code ALLTHEHACKS20)
Credit Cards
ATH Podcast
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Ep 166: Best Award Search Tools for Booking Flights with Points & Miles with Greg the Frequent Miler
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Ep 227: The Path to Becoming an Expert in Points & Miles with Devon Gimbel
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AMA: Submit A Question
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Leave a review: Apple Podcasts | Spotify
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Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com
Full Show Notes
(00:00) Introduction
(01:10) Two Ways to Use Points for Travel
(06:30) Define Your Flexibility Before You Search
(11:42) Clarify What You Actually Want From A Trip
(15:00) When to Start Planning (and Why Earlier Is Almost Always Better)
(18:48) How To Find Award Availability
(19:55) The Best Award Search Tools & How to Use Them
(21:17) How Award Tools Work
(23:30) Using Alerts To Find Better Flights
(26:15) What To Do When You Can’t Find Availability
(28:31) How to Book for a Group When Availability Is Tight
(31:32) Why You Should Book One-Way Flights
(32:27) How To Use Points For Domestic Flights
(34:38) The Best Tool For Domestic Award Searches
(35:05) Why Diversifying Your Points Unlocks More Domestic Options
(36:36) Should You Ever Use Points to Upgrade Seats?
(39:00) Are Travel Portals Worth It?
(39:36) The Case Against Using Travel Portals
(42:09) The Case For Using Travel Portals
(45:17) How To Think About Chase Points Boost
(48:26) When Using Points For Hotels Makes Sense
(50:50) The Best Ways to Earn Hotel Points
(53:54) The Award Booking Index Card
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Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.
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