18 Tactics for Booking Travel with Points & Miles
Author: Chris Hutchins
July 23, 2025
Duration: 54:44
#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.
Link to Full Show Notes: https://chrishutchins.com/18-tactics-for-booking-award-travel
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Resources Mentioned
Chris' Airline/Hotel Transfer Partner Spreadsheet
Free Starter Guide to Points by Devon Gimbel
Award Search/Discovery Tools
point.me: 20% off annual plans with code ALLTHEHACKS20
Seats.Aero: Lufthansa First Class Finder | Qatar Qsuites Finder | JAL First Class Finder
PointsYeah: Daydream Explorer
AwardTool: $20 off annual plans with code ALLTHEHACKS
Awayz: $10 for ATH listeners and 50% off for ATH members
MaxMyPoint
StayWithPoints
Rooms.Aero
Points Path Chrome Extension
FlightConnections
Skiplagged
Other Resources
Award change/cancel policies by airline
The best programs for lap infant award tickets
Frequent Miler Podcast: How to Save Miles by Flying More
ATH Podcast
Ep #166: Best Award Search Tools for Booking Flights with Points & Miles with Greg the Frequent Miler
Ep #167: Best Tools for Booking Hotels with Points & Miles with Greg the Frequent Miler
Ep #227: The Path to Becoming an Expert in Points & Miles with Devon Gimbel
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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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