July 23, 2025

18 Tactics for Booking Travel with Points & Miles

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18 Tactics for Booking Travel with Points & Miles

#238: Chris shares 18 tactics he’s used to get the best deals booking flights and hotels with points. Learn how to leverage flexibility, navigate transfer partners, use the right tools, identify “sweet spots,” avoid high fees, position flights, and so much more.

 

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Resources Mentioned

Chris' Airline/Hotel Transfer Partner Spreadsheet

Free Starter Guide to Points by Devon Gimbel

Award Search/Discovery Tools

Other Resources

ATH Podcast

 

Full Show Notes

(00:00) Introduction

(01:54) Quick Episode Overview

(03:25) Leveraging Flexibility to Unlock Travel Opportunities

(06:47) The Importance of Understanding Airline Partners

(07:15) Comparing Award Flight Deals

(09:51) Different Cancellation Policies Across Airline Programs

(12:37) Expiration Policies

(14:11) Understanding Schedule Opens and Booking Windows

(16:55) Award Search Tools

(22:13) When and Why You Should Buy Points on Sale

(23:35) Finding Award Sweet Spots

(26:20) Leveraging Transfer Bonuses

(29:00) Why You Should (Almost) Always Book One-Way Travel

(31:07) How to Strategically Position Long-Haul Flights

(34:40) Taking Advantage of Stopovers and Open Jaws

(40:30) Pros (and Cons) of Mixed Cabin Awards

(42:56) Setting Up Alerts to Find the Ideal Flight

(44:56) Booking Backup Flights

(46:25) Three Biggest Pain Points of Award Bookings

(48:31) Hidden City Ticketing

(52:16) Tips for Hotel Award Deals

(53:42) Airline Pricing for Lap Infants and Children

(55:39) Outsized Value from the Southwest Companion Pass

 

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