18 Tactics for Booking Travel with Points & Miles

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 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: podcast@allthehacks.com 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

Ever feel like there's a smarter, more efficient way to navigate your finances, your travels, and your daily routines? That's the core question driving All the Hacks: Money, Points & Life. Hosted by Chris Hutchins, this podcast is built on a simple, powerful idea: maximizing value doesn't mean sacrificing enjoyment. Instead, it's about the strategic choices that free up resources-both money and time-for what truly matters. Chris approaches life as a series of systems to be optimized, drawing from his own experience saving millions through meticulous analysis. The conversations here are practical and wide-ranging, moving seamlessly from credit card points strategies and investment philosophies to the less tangible hacks for personal fulfillment. You'll hear from a diverse roster of experts and icons, including Tim Ferriss, Tony Hawk, Codie Sanchez, and Gary Vaynerchuk, who all bring their unique perspectives on building wealth and designing a compelling life. Each episode feels like a focused workshop, offering actionable advice you can use immediately, whether it's planning a luxury vacation for a fraction of the cost or rethinking your approach to career and leisure. This isn't just about frugality; it's about unlocking freedom and excitement through smarter decisions. Tune in for a consistently insightful blend of tactical moves and deeper conversations that challenge the conventional trade-offs between spending, saving, and living well.
Author: Language: English Episodes: 100

All the Hacks: Money, Points & Life
Podcast Episodes
The Custom Everything Era with Kevin Rose [not-audio_url] [/not-audio_url]

Duration: 1:07:14
#275: Chris and Kevin dig into how they're actually using AI tools in their daily lives right now. They explore real-world AI use cases, the tradeoffs of sharing personal data, the collapse of trust online, and what all…
The Surprising History of Points and Miles [not-audio_url] [/not-audio_url]

Duration: 42:25
#274: Chris walks through the complete history of points and miles and breaks down the $140 billion machine behind them, so you can get more out of every point you earn. He covers the legal accidents that made credit car…
Stop Overthinking and Start Deciding with Derek Sivers [not-audio_url] [/not-audio_url]

Duration: 1:52:11
#273: Learn to stop overthinking and make better decisions. Chris and Derek discuss how optimizing can go wrong, a coin flip trick for making decisions, journaling as a superpower, how your actions might reveal what you…
My Process for Booking Travel with Points & Miles [not-audio_url] [/not-audio_url]

Duration: 54:29
#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…
How to Actually Live the Life You're Optimizing For with Sahil Bloom [not-audio_url] [/not-audio_url]

Duration: 56:41
#271: Learn why over-optimizing your life can quietly destroy the things you actually care about. Chris and Sahil explore the doorman fallacy, why big life decisions should happen fast, how to use AI as a thinking partne…
Ski Trip Mishaps, AI Interior Design, Reflecting on Life and More [not-audio_url] [/not-audio_url]

Duration: 1:08:15
#270: Chris and Amy discuss lessons from three ski trips with kids, using AI to redesign rooms on a budget, their favorite new gadgets, navigating high-deductible health plans, and more. Link to Full Show Notes: https://…
Credit Cards: What's in My Wallet for 2026 [not-audio_url] [/not-audio_url]

Duration: 1:14:45
#267: Chris reviews his credit card lineup for 2026, sharing which cards he's keeping and canceling and why. He also covers how to evaluate annual fees, the best cards across major spending categories, and the apps he us…
Why Change Is Hard and How to Make It Your Advantage with Maya Shankar [not-audio_url] [/not-audio_url]

Duration: 45:22
#266: Chris and Maya break down the science-backed tools that make change easier and more intentional. They explore why most people misunderstand change, how to anchor your identity to your deeper “why,” and practical to…