Episode Details

Our Trip Fell Apart (But Our Points Didn't) — Plus How to Travel for Free with Kids

A Southwest delay killed our Charleston beach trip — but because it was booked on points, we walked away without losing a dime. Here's exactly how we unwound three different award bookings, plus a full breakdown of how to earn and use points to travel with kids for free.

Melissa was supposed to be recapping a family beach getaway to Wild Dunes, a Hyatt resort near Charleston. Instead, a cascading Southwest delay forced a last-minute cancellation — and this episode walks through how to cancel an award flight, an award hotel stay, and a rental car booking without eating the cost. Then it's a deep dive into the credit card and points strategy that makes free family travel possible in the first place.

In This Episode

• How to cancel an award flight and get every point back
• What really happens when you cancel a hotel award stay inside the cancellation window
• Two ways to avoid a last-minute hotel cancellation fee
• Why rental car bookings through travel portals (Capital One, Chase, Priceline) can get complicated
• Why earning points is harder for families than solo travelers
• The fastest way to earn points: credit card sign-up bonuses
• Best starter cards for family travel (Chase Sapphire Preferred, Ink Business)
• How to search and book award flights (Google Flights, PointsYeah, AwardTool, airline alliances)
• What a repositioning flight or drive is, and when it's worth it
• The Southwest Companion Pass strategy for families
• Hotel points strategy for families (Hyatt, IHG, Hilton, Choice)
• Practical tips for booking flights and hotel rooms with kids

Chapters

00:00 Intro & catching up 
01:00 The Wild Dunes trip and the cancellation cascade 
03:00 Unwinding the points: flight, hotel, and rental car 
08:30 Why points are harder to use for families 
09:30 Earning points: sign-up bonuses and transferable points 
13:00 Booking award flights (tools, alliances, repositioning) 
18:30 The Southwest Companion Pass 
20:30 Hotel strategies: Hyatt, IHG, Hilton, Choice 
25:00 Practical tips and wrap-up

Chase Sapphire credit cards
Best Travel Credit Cards for Families
Southwest Companion Pass
Four Reasons I LOVE Award Travel
How to get discounted rental cars
Chase Freedom credit cards
Chase Ink Business credit cards
Capital One Venture X credit card

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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