My Process for Booking Travel with Points & Miles

All the Hacks: Money, Points & Life

Chris Hutchins

Business, Society & Culture, Education, Self-improvement, Investing, Places & Travel

4.8 • 1.6K Ratings

🗓️ 1 April 2026

⏱️ 57 minutes

🔗️ Recording | iTunes | RSS

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Summary

#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 Partner Deals Gelt: ⁠Skip the waitlist on personalized tax guidance to maximize your wealth Bilt Rewards: ⁠Earn the most valuable points when you pay rent DeleteMe: ⁠20% off removing your personal info from the web Wispr Flow: ⁠Try effortless voice dictation for free Green Chef: ⁠50% off your first month + 20% off for two months with code 50ALLTHEHACKS For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals Resources Mentioned Award Search Tools AwardTool ($20 off annual plans with code ALLTHEHACKS) point.me (20% off annual plans with code ALLTHEHACKS20) PointsYeah Seats.Aero Points Path Browser Extension FlightConnections Credit Cards Best Cards Page CardTool App Marriott Bonvoy Brilliant® American Express® Card ATH Podcast Ep 166: Best Award Search Tools for Booking Flights with Points & Miles with Greg the Frequent Miler Ep 227: The Path to Becoming an Expert in Points & Miles with Devon Gimbel Ep 238: 18 Tactics for Booking Travel with Points & Miles Ep 244: How I Saved $10,000+ on Luxury Hotels Ep 258: My Top 5 Mistakes with Points & Miles Membership AMA: Submit A Question Leave a review: Apple Podcasts | Spotify 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 Connect with Chris ⁠⁠Newsletter⁠⁠ | ⁠Membership⁠⁠ | ⁠X⁠⁠ | ⁠Instagram⁠⁠ | ⁠LinkedIn⁠⁠ 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. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	If you had to fit the core principles of maximizing point redemptions on a three by five index card,
0:05.5	what would it say? Well, I got that question from a listener named Matt, and I loved it so much.
0:09.9	I'm going to build this entire episode around it. But I'm not going to just stop there,
0:13.7	because I'm going to take a dozen of your questions about booking travel with points and miles
0:17.7	and organize them into a walkthrough of the entire process end-to-end,
0:21.9	not just the theory, but the actual steps, answering your questions along the way,
0:26.9	so it's kind of like an AMA episode as well.
0:29.4	We'll cover why the same business class seat can cost 240,000 miles or 64,000 miles,
0:34.2	depending on how you book it, and what to do when a route looks impossible to find
0:38.2	availability. I'll share how my thinking on travel portals has evolved. We'll talk about domestic flights
0:43.7	and how things change there and whether it ever makes sense to use your points to upgrade. Whether
0:48.3	you've never transferred a point in your life or you're deep in the game, I really think there's
0:51.9	going to be something here for you. But fair warning, by the end, you might need a magnifying glass and very tiny handwriting to fit
0:58.6	everything we cover on one index card like Matt asked for.
1:02.0	I'm Chris Hutchins.
1:02.9	If you enjoy this episode, leave a comment or share it with a friend.
1:05.8	And if you want to keep upgrading your money points in life, click follow or subscribe.
1:14.5	All right, before we get any further, I think we need to understand the fundamental mechanic that makes this whole points of miles game worth playing.
1:18.4	I've talked about this before, but I'll just say briefly, there are two primary ways you
1:23.2	can use your credit card points for travel. Option A is kind of the easy mode, which oftentimes we get targeted to do is to just use
1:31.9	the travel portal.
1:33.1	You go to Chase Travel, Amex Travel, you search for a flight the way you'd search on Google
	...

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