My Process for Booking Travel with Points & Miles

Podcast: All the Hacks: Money, Points & Life (LS 60 · TOP 0.1% what is this?)
Episode: My Process for Booking Travel with Points & Miles
Pub date: 2026-04-01

Get Podcast Transcript →
powered by Listen411 - fast audio-to-text and summarization

#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: [email protected]

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

The podcast and artwork embedded on this page are from Chris Hutchins, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.