Ready for Takeoff: An affordable family getaway to Disneyland and San Diego

Ready for Takeoff is a weekly series that helps readers like you find the best ways to book post-pandemic adventures with points and miles.

Reader Christopher Kellough reached out for tips on planning a post-pandemic family vacation to Southern California. He will be traveling with his wife and their two children, hoping to visit Disneyland before spending a few days in sunny San Diego. This trip is quite manageable for a family of four, with budget-friendly options for flights and accommodations this summer.

Hello TPG team,

While my wife and I have a long list of international destinations we want to explore, we’re holding off until our kids (ages 6 and 2) are a bit older and can manage a long flight. In the meantime, here’s a trip we’re excited to plan for next year.

Departure: MCO

Destination: Southern California (2 adults, 2 kids - ages 7 and 3)

We have a strong passion for Disneyland and plan to visit the parks as soon as the kids are vaccinated and they welcome out-of-state visitors. We also want to break from our usual routine and take the kids to explore San Diego for a few days.

We typically stay at a Disney resort, so our point redemption options there are limited, but we hope to use our points for an excellent flight and/or hotel in San Diego. We're open to flying into any Southern California airport!

Points Available: 220,000 Chase UR & 155,000 AmEx MR

Excited to dive into the series!

Thank you,

Christopher Kellough

Reward Points

Christopher appears to have an ideal mix of rewards to cover both flights and accommodations. His transferable rewards offer him various options for booking the family trip to Southern California.

• 220,000 Chase Ultimate Rewards
• 155,000 Amex Membership Rewards

Flights to Southern California

This summer, flights from Orlando to Southern California are remarkably affordable. In August, Christopher can book a Delta flight starting at just 16,000 SkyMiles and $12 for a round-trip. For his family of four, he could transfer 64,000 Membership Rewards to Delta and pay $48 in taxes out of pocket.

Traveling with children typically means more than just a carry-on, which can add to the cost. If Christopher has a Delta co-branded credit card that offers free checked bags, flying basic economy should be manageable.

How to redeem points for this award

The booking process for both Southwest and Delta is quite simple.

Step 1: Sign In

Ensure you are logged into your account prior to searching for award availability. This will facilitate a smoother booking experience.

Step 2: Input Your Flight Details

On the main page, input your destination and select "My dates are flexible" to display the fare calendar.

To find the best fare for each leg of your journey, you'll want to search for each flight segment separately (MCO-SNA, then SAN-MCO). This will bring up a calendar like this:

Next, you can perform a one-way calendar search for the San Diego (SAN) to Orlando (MCO) leg. Make sure to input each segment along with the specific date you wish to book. The airport codes for John Wayne (SNA) and San Diego (SAN) are quite similar, so double-check that you enter the correct one for each leg.

Step 3: Choose flights one at a time

Typically, I’d suggest returning to the homepage after selecting your dates and choosing "Multi-City" to book this trip as a single award. However, I’ve noticed that the lowest rates aren’t available for multi-city bookings. Therefore, I recommend that Christopher book each leg separately.

It’s quite straightforward: Once you reach the calendar, pick the date that suits you best. On the following page, select your flight. Keep in mind that the 7,500-Skymile fare is for basic economy. If you prefer to avoid those limitations, you can opt for a main cabin seat for an additional 2,500 miles.

Step 4: Complete the booking

On the subsequent page, you’ll find a summary of your ticket price, along with options to upgrade to a higher class.

Accommodations near Disneyland and San Diego

With 220,000 Chase Ultimate Rewards points, Christopher's best option is to redeem them at Hyatt hotels in Anaheim and San Diego. Hyatt boasts a variety of excellent properties. The closest Hyatt to Disneyland is the Hyatt House at Anaheim Resort/Convention Center, featuring spacious rooms with pull-out sofas. Guests can enjoy on-site laundry facilities and complimentary breakfast, making it both convenient and economical.

In San Diego, there are two Category 4 Hyatt hotels available for 15,000 points per night: The Andaz San Diego and Manchester Grand Hyatt San Diego. Both offer double beds suitable for four guests. The Grand Hyatt is situated near the harbor, while the Andaz is in the vibrant Gaslamp Quarter. For a family of four, the Grand Hyatt's location near the New Children's Museum and public transport is ideal for easy exploration of the city.

How to book these hotels using points

He has two choices depending on his travel dates: transfer points to Hyatt or book through the Chase Ultimate Rewards travel portal. The optimal choice will depend on the current room rates.

For instance, a night at the Hyatt House at Anaheim Resort/Convention Center will require 15,000 points.

Chase Sapphire Preferred cardholders can redeem their points via the Ultimate Rewards travel portal at a rate of 1.25 cents each. If the hotel’s rates are under $187.50, it's more advantageous to book through Chase. At that price point, he’ll need fewer than 15,000 Ultimate Rewards points per night, making it cheaper than transferring to Hyatt.

If Christopher holds a Chase Sapphire Reserve, his points are valued at 1.5 cents each. If room rates drop below $225, he should redeem his points through the Ultimate Rewards travel portal. Here’s a step-by-step guide to do that:

Step 1: Sign in to your Chase account, then look to the right side of the page to find a box displaying your total Ultimate Rewards balance. Click on it to be taken to the Ultimate Rewards dashboard.

Step 2: Select "Travel" to go to the travel homepage, where you can search for hotel options.

Step 3: Scroll down until you find the property you wish to book and follow the provided prompts.

Booking hotels directly on the Hyatt website is simple. Visit the home page, enter your desired city, and ensure the "Use points" option is selected.

How to accumulate hotel points

Christopher has ample points to cover his hotel stay, but if you’re looking to earn Hyatt points, the Chase Sapphire Preferred is an excellent choice. This card currently offers 60,000 bonus points after you spend $4,000 within the first three months of opening your account.

Ultimate Rewards transfer to Hyatt at a 1:1 ratio, meaning the bonus could provide you with enough points for up to six nights at the mentioned Hyatt properties.

Ground transportation

The family can travel from Anaheim to San Diego using Amtrak for $31 per person each way. This option helps them bypass the ongoing car rental shortage in the area. However, renting a car would be more convenient for a family of four.

As anticipated, rental rates are quite high in August. For a week-long rental at the end of the month, you can expect to spend over $800. Although you can redeem Ultimate Rewards at a rate of 1.25 to 1.5 cents per point, that still requires a significant number of points.

In conclusion

Traveling from Orlando to Southern California can be quite economical when using points, even for a family of four. While dynamic pricing can cause concern for many travelers, it can actually work out well—especially during the busy summer season. TPG wishes Christopher and his family a fantastic trip to Disneyland and San Diego!

If you have a destination in mind and need assistance with your points strategy, send us an email to be featured in the next edition of Cleared for Takeoff.

Image courtesy of Disneyland Resort