My Process for Booking Travel with Points & Miles

My Process for Booking Travel with Points & Miles

Author: Chris Hutchins April 1, 2026 Duration: 54:29
All the Hacks: Money, Points & Life
BusinessCultureEducationInvestingPlacesSocietySociety & CultureTravel
#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 vs. transfers, plus the mindset shifts that make the whole process work. Link to Full Show Notes: https://chrishutchins.com/booking-travel-with-points-and-miles-2026 Partner Deals Gelt: ⁠Skip the waitlist on personalized tax guidance to maximize your wealth Bilt Rewards: ⁠Earn the most valuable points when you pay rent DeleteMe: ⁠20% off removing your personal info from the web Wispr Flow: ⁠Try effortless voice dictation for free Green Chef: ⁠50% off your first month + 20% off for two months with code 50ALLTHEHACKS For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals Resources Mentioned Award Search Tools AwardTool ($20 off annual plans with code ALLTHEHACKS) point.me (20% off annual plans with code ALLTHEHACKS20) PointsYeah Seats.Aero Points Path Browser Extension FlightConnections Credit Cards Best Cards Page CardTool App Marriott Bonvoy Brilliant® American Express® Card ATH Podcast Ep 166: Best Award Search Tools for Booking Flights with Points & Miles with Greg the Frequent Miler Ep 227: The Path to Becoming an Expert in Points & Miles with Devon Gimbel Ep 238: 18 Tactics for Booking Travel with Points & Miles Ep 244: How I Saved $10,000+ on Luxury Hotels Ep 258: My Top 5 Mistakes with Points & Miles Membership AMA: Submit A Question Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com Full Show Notes (00:00) Introduction (01:10) Two Ways to Use Points for Travel (06:30) Define Your Flexibility Before You Search (11:42) Clarify What You Actually Want From A Trip (15:00) When to Start Planning (and Why Earlier Is Almost Always Better) (18:48) How To Find Award Availability (19:55) The Best Award Search Tools & How to Use Them (21:17) How Award Tools Work (23:30) Using Alerts To Find Better Flights (26:15) What To Do When You Can’t Find Availability (28:31) How to Book for a Group When Availability Is Tight (31:32) Why You Should Book One-Way Flights (32:27) How To Use Points For Domestic Flights (34:38) The Best Tool For Domestic Award Searches (35:05) Why Diversifying Your Points Unlocks More Domestic Options (36:36) Should You Ever Use Points to Upgrade Seats? (39:00) Are Travel Portals Worth It? (39:36) The Case Against Using Travel Portals (42:09) The Case For Using Travel Portals (45:17) How To Think About Chase Points Boost (48:26) When Using Points For Hotels Makes Sense (50:50) The Best Ways to Earn Hotel Points (53:54) The Award Booking Index Card 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

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All the Hacks: Money, Points & Life
Podcast Episodes
Deep Dive on Bilt Rewards and New Bilt 2.0 Cards [not-audio_url] [/not-audio_url]

Duration: 1:15:43
#264: Learn how the Bilt ecosystem works, from earning Bilt Rewards to the new cards, transfer partners, perks, and where the real value is. Whether you’re new or already earning, this is a practical guide to using Bilt…
How to Earn Millions of Points and More Listener Q&A [not-audio_url] [/not-audio_url]

Duration: 1:04:43
#263: Chris breaks down exactly how he’s earned millions of points and miles, and why simplicity matters more than optimization. He covers signup bonuses, spending strategies, credit score impacts, business cards, cash-b…
Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose [not-audio_url] [/not-audio_url]

Duration: 1:09:45
#261: Chris and Kevin reflect on 2025’s biggest wins and lessons, then dive into how they're planning 2026. They share their goals, the tools they're using, and why they're designing a year that’s easier, not just more o…
Top 10 Takeaways from 2025 [not-audio_url] [/not-audio_url]

Duration: 37:24
#260: Chris distills the most powerful lessons from over 50 episodes in 2025 into 10 actionable takeaways that changed how he thinks about money, time, health, relationships, purpose, and more. Link to Full Show Notes: h…
Choosing the Problems Worth Struggling For with Mark Manson [not-audio_url] [/not-audio_url]

Duration: 59:44
#259: Learn how to pick the challenges in life that actually matter. We break down how to stop optimizing for the wrong things, why values trump goals in decision-making, practical strategies for building real friendship…
My Top 5 Mistakes with Points & Miles [not-audio_url] [/not-audio_url]

Duration: 54:54
#258: The 5 biggest mistakes Chris has made in his points & miles journey. He dives into the hidden cost of status, the math behind point values, the power of opportunity cost, and why hoarding points quietly destroys va…
End of Year Checklist for Your Taxes, Points and Miles [not-audio_url] [/not-audio_url]

Duration: 1:13:17
#257: We break down essential tax and financial decisions to make before year-end. Learn how to maximize deductions, optimize charitable giving, manage investment gains and losses, and take advantage of retirement and ho…
2025 Holiday Gift Guide and Top Ways to Save This Season [not-audio_url] [/not-audio_url]

Duration: 1:24:30
#255: Here are 100+ holiday gift ideas across tech, kitchen, home, clothing, fitness, kids, and games. I’ll also share tools and tactics to help you find deals and spend less this holiday season. For all the products, li…

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