18 Tactics for Booking Travel with Points & Miles

All the Hacks with Chris Hutchins

Chris Hutchins

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

4.7 • 1.4K Ratings

🗓️ 23 July 2025

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

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Summary

#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 Partner Deals MasterClass: Learn from the world's best with 15% off Trust & Will: Get 20% off personalized, legally binding estate plans Vuori: 20% off the most comfortable performance apparel I've ever worn Superhuman: Free month of the fastest and best email with code ALLTHEHACKS Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals 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 Newsletter: Subscribe here Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: [email protected] 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 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	Traveling for free isn't just about earning points.
0:05.0	It's about using them smartly.
0:07.0	But if you've ever searched for a ward space and come up empty,
0:10.0	burn more points than you should have,
0:12.0	or run into other roadblocks getting the most out of your points in miles,
0:16.0	don't worry, you're not alone. It's something we all face.
0:19.0	So today I'm going to share 18 of my favorite
0:21.7	tricks for actually redeeming those points for flights and hotels, including how to find the best
0:27.1	deals, navigate airline rules, and make sure you're never stuck paying more than you should.
0:32.2	I'm Chris Hutchins. If you enjoy this episode, please share it with a friend or leave a comment or
0:36.4	review. And if you want to
0:37.8	keep upgrading your life, money, and travel, click follow or subscribe. Now let's get into it right after
0:43.5	this. This episode is brought to you by Masterclass. There is nothing like gaining fresh
0:50.4	perspective from experts who've seen it all and have the wisdom to prove it.
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0:59.7	negotiate.
1:00.5	I know it did for me.
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1:07.2	taught by the world's best business leaders, writers, chefs, and more.
1:11.6	You can unlock investing fundamentals straight from Wall Street Titans, learn how to leverage
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1:21.6	Bob Iger, Howard Schultz, and more, all through Masterclass.
	...

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