DiscoverAll the Hacks: Money, Points & Life18 Tactics for Booking Travel with Points & Miles
18 Tactics for Booking Travel with Points & Miles

18 Tactics for Booking Travel with Points & Miles

Update: 2025-07-23
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Description

#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



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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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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18 Tactics for Booking Travel with Points & Miles

18 Tactics for Booking Travel with Points & Miles

Chris Hutchins