#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
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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
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