Turning the Tables: My Approach to Points, Miles and Travel

#295: Chris shares the strategies he actually uses to earn, spend, and maximize millions of points and miles. He breaks down how many credit cards most people really need, his approach to booking award travel for a family, the rise of massive card-member flight discounts, when to pay cash vs. points, and some of his favorite—and most unusual—redemptions. Meghan Coyle and Sally French are the hosts of NerdWallet's Smart Travel podcast, a weekly show on travel news, loyalty programs and travel credit cards that helps listeners travel more and pay less. Link to Full Show Notes: https://chrishutchins.com/award-flights-card-strategy-nerdwallet Partner Deals Gusto: ⁠Free 3-month trial of the #1 payroll software Gelt: ⁠Skip the waitlist on personalized tax guidance to maximize your wealth LMNT: ⁠Free sample pack of my favorite electrolyte drink mix Wispr Flow: ⁠Try effortless voice dictation for free Bilt Rewards: ⁠Earn the most valuable points when you pay rent For all the deals, discounts and promo codes from our partners, go to: ⁠chrishutchins.com/deals Resources Mentioned NerdWallet Smart Travel podcast Meghan Coyle Sally French Award Search & Points Tools Seats.aero PointsPath (15% off with ALLTHEHACKS15) PointsYeah Shopping Portals, Gift Cards & Offers Rakuten Capital One Shopping Rove GCX SavenDeals ATH Podcast #290: The New Rules of Points & Miles in 2026 with Brian M Chris' Credit Card Optimizer Hotel Upgrade Program Best Cards Page Gift Cards Page Newsletter AMA: Submit Questions Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com Full Show Notes (00:00) Introduction (02:06) How Chris Got Into Points & Miles (05:01) When Chris Became a Points & Miles “Expert” (07:25) Paying for a Wedding Video With Delta Miles (13:38) Why Chasing an Extra Point per Dollar Doesn't Move the Needle (15:34) The Optimal Two-Card Strategy (16:50) Maximizing Points Without Overspending (19:52) Should You Buy Gift Cards to Earn More Points? (22:36) Booking Award Travel for a Family (25:06) Chris’ Strategy for Finding Award Flights (27:34) Leveraging Flexibility and Award Search Tools (31:45) What to Do With Points If You Don't Want to Play the Game (34:30) Setting Alerts and Picking One Award Search Tool (37:01) The Huge Discounts Hidden Behind Airline Credit Cards (39:21) The Risks of Speculative Bookings (41:08) When Chris Breaks His Own Transfer Rule (45:15) The Easiest Way to Redeem Points When You Don't Want the Hobby (47:17) Are Hotel Redemptions Easier Than Flights? (51:07) The Real Math Behind Cash vs. Points (55:02) Chris's Rule of Thumb for Comparing Cash and Points (56:12) A Trick for Getting Refunds on Flights You Need to Cancel (59:03) Chris’ Take on the New Southwest 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