My Process for Booking Travel with Points & Miles

#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-2026Partner DealsGelt: ⁠Skip the waitlist on personalized tax guidance to maximize your wealthBilt Rewards: ⁠Earn the most valuable points when you pay rentDeleteMe: ⁠20% off removing your personal info from the webWispr Flow: ⁠Try effortless voice dictation for freeGreen Chef: ⁠50% off your first month + 20% off for two months with code 50ALLTHEHACKSFor all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/dealsResources MentionedAward Search ToolsAwardTool ($20 off annual plans with code ALLTHEHACKS)point.me (20% off annual plans with code ALLTHEHACKS20)PointsYeahSeats.AeroPoints Path Browser ExtensionFlightConnectionsCredit CardsBest Cards PageCardTool AppMarriott Bonvoy Brilliant® American Express® CardATH PodcastEp 166: Best Award Search Tools for Booking Flights with Points & Miles with Greg the Frequent MilerEp 227: The Path to Becoming an Expert in Points & Miles with Devon GimbelEp 238: 18 Tactics for Booking Travel with Points & MilesEp 244: How I Saved $10,000+ on Luxury HotelsEp 258: My Top 5 Mistakes with Points & MilesMembershipAMA: Submit A QuestionLeave a review: Apple Podcasts | SpotifyEmail for questions, hacks, deals, and feedback: [email protected] 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 CardConnect with Chris⁠⁠Newsletter⁠⁠ | ⁠Membership⁠⁠ | ⁠X⁠⁠ | ⁠Instagram⁠⁠ | ⁠LinkedIn⁠⁠Editor’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.