You’ve probably seen plenty of Disney guides online already. On sites like Mafengwo and Qyer, travel experts have written page after page of incredibly detailed tips, which really shows just how deep the Disney rabbit hole goes. A few days ago, I also spent four days at Disney in Orlando. Naturally, as someone who knows a bit about credit cards and airline miles and points, I look at trip planning from a slightly different angle. This series is mainly divided into: using points to book flights and the actual itinerary, booking hotels and the actual stay, and choosing ground transportation. These are all planning ideas that can be applied to travel in other destinations as well. Next, I’ll cover money-saving strategies specifically for Disney, a rough itinerary overview, my impressions of the various attractions, and a few thoughts on Disney overall.

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Trip Planning

To be honest, I’ve always been the kind of person who lets someone else plan the trip and then just tags along. This was the first time I had to plan everything myself for a trip with my wife. Fortunately, it all worked out pretty well, and we had a great time. In fact, planning a trip for two is actually pretty simple: just lock down a few key points, and then you can play the rest by ear. There’s no need to plan every hour or every single step in exhausting detail.

The most important pieces are: flights, hotels, and transportation. Flights should definitely be booked first, because cheap cash fares or award tickets often don’t give you much flexibility on timing. Once the flights are set, you can match the hotel and ground transportation accordingly and minimize time spent on the road.

Because of our itinerary, I needed two flights: ORD (Chicago) to MCO (Orlando International Airport), and then Orlando area airport to a small city. The goal, of course, was either to redeem miles in the best possible way or simply spend as little cash as possible.

Flight: ORD-MCO

Here are a few options I considered (all prices are per person):

  • UA award ticket: 12,500 + $80 (because the booking was made within 21 days of departure, there was an additional $75 ticketing fee)
  • AA award ticket: 12,500 + $80 (because the booking was made within 21 days of departure, there was an additional $75 ticketing fee)
  • BA booking an AA award: 7,500 + $5.6 (using BA to book an AA award avoids the within-21-days ticketing fee, and taxes are very low)
  • Cheapest cash ticket: $139 (AA), found via Google Flights
  • Book with TYP and Prestige: 8,700 (using TYP with Prestige at 1.6 cents per point)
  • Book with UR or MR: 11,600 (UR or MR can be used through the issuer travel portal at 1.2 cents per point)
  • Use a US Airways companion ticket

So how do you choose among all these options? First, the extra fee on award tickets booked within 21 days is too large relative to the cost of a domestic U.S. ticket. On top of that, AA and UA miles are generally more valuable for round-trip flights between the U.S. and China, so I immediately passed on the first two options. As for the UR/MR option, the overall value of those points is obviously much higher than $139, so that was also an easy pass. The US Airways companion ticket requires a round trip, so it clearly didn’t fit here either.

That left BA, paying cash, and using TYP. The downside of booking an award through BA is that you won’t earn miles for the flight, but getting 1.8 cents per point in value from BA makes it the clear first choice. Unfortunately, no BA award seats were available for that day. So I had to settle for either paying cash or using TYP. If you have TYP and a Prestige card, then booking with points is obviously the better choice. After all, points are meant to be used; if you just sit on them, they’ll only get devalued over time. One nice thing about booking through TYP is that the ticket still earns airline miles. The ORD-MCO one-way earned 1,000 miles, which is a nice little bonus. Here was the final redemption: the two of us spent a total of 17,300 TYP.

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Before the ORD-MCO flight, we also stopped by the AA Club at ORD. We used a US Airways Club pass that came with a US Airways credit card I applied for last year (it’s now an AA Admiral Club pass). One pass allowed entry for me plus one guest. One thing to note: the staff at the entrance may check the name on the pass against your ID.

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There wasn’t a ton of food in the Club—mostly some small cookies, coffee, soup, and vegetables like carrots—but the coffee was pretty good. The Club also had its own Wi-Fi and display screens showing all departures and arrivals, which was quite convenient.

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There was one small twist at the end: when we got back to the gate, we found out our flight had been delayed. So we walked back to the Club, explained the situation to the staff, showed the Club pass we had used earlier, and got back in for another relaxing hour.

Here are some of the award-search tools I used for this trip, in case they’re helpful:

  • gcmap.com: Mainly used to check distance, so you can figure out how many BA miles are needed; also commonly used for planning complex hop-by-hop itineraries
  • https://wandr.me/Award-Search/Avios-Map/: A great BA search tool that tells you whether there is a nonstop flight between two cities and how many BA miles are required
  • AA/UA official websites: Search for award tickets
  • https://www.google.com/flights/: Very useful Google flight search tool; it often finds cheap fares and can link you to the airline website to purchase directly (the fares it finds are often similar to what appears in Citi Travel, so you can search here first and then check Citi Travel)

Follow the rest of the series for my Orlando Disney guide: