You are using an older browser version. Please use a supported version for the best MSN experience.

Cleared for Takeoff: A budget-friendly family trip to Disneyland and San Diego

The Points Guy logo The Points Guy 6/22/2021 Ariana Arghandewal
a man standing in front of a building talking on a cell phone © Provided by The Points Guy
MSN has partnered with The Points Guy for our coverage of credit card products. MSN and The Points Guy may receive a commission from card issuers.

Cleared for Takeoff is a weekly series showing readers like you the best ways to book post-pandemic adventures using points and miles. If you’d like tips on booking your own trip using miles, please email us with your preferred itinerary and current mileage balance.

Reader Christopher Kellough reached out to us for advice on booking a post-pandemic family vacation to Southern California. Christopher is traveling with his wife and two kids. They want to do a trip to Disneyland, followed by a few days in sunny San Diego. This is a fairly easy getaway for a family of four and there are affordable options for flights and hotels this summer.

Hi TPG team,

While my wife and I have a bunch of international destinations on our bucket list, we are waiting until the kids (currently 6 & 2) are a little bigger to handle the long flight. Until then, here’s a trip we’re hoping to take next year.

Origin: MCO

Destination: Southern California (2 adults, 2 kids – will be 7yo & 3yo)

We have a big Disneyland habit and hope to hit up the parks as soon as the kids are vaccinated and they open to out-of-staters. We also want to branch out from our routine and take the kids down to explore San Diego for a few days as well.

We usually stay at a Disney resort so don’t have a lot of point redemption options there, but hope to use our points for a great flight and/or hotel in San Diego. Open to flying into any SoCal airport!

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

Looking forward to reading the series!


Christopher Kellough

For more TPG news delivered each morning to your inbox, sign up for our free daily newsletter!

In This Post

Points stash

Christopher seemingly has the perfect rewards balance to cover both airfare and hotels. Transferrable rewards give him multiple options when it comes to booking his family vacation to Southern California.

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

Airfare to Destination X

Flights between Orlando and Southern California are incredibly cheap this summer. In August, Christopher can fly Delta start at just 16,000 SkyMiles and $12 round-trip. For a family of four, Christopher could transfer 64,000 Membership Rewards to Delta and pay $48 in taxes out of pocket.

Traveling with kids often requires more than just a carry-on bag, so this is a potential added cost to consider. If Christopher has a Delta co-branded credit card with free checked bag privileges, then flying basic economy shouldn’t be a problem

How to book this award with points

The booking process for both Southwest and Delta is pretty straightforward.

Step 1: Log in

Make sure you’re logged into your account before searching for award space. This will ensure the smoothest booking process.

Step 2: Enter your flight information

On the homepage, enter your travel destination and check off “My dates are flexible” to generate the fare calendar.

If you just want to find the lowest fare for each segment, you’ll want to search each flight segment (MCO-SNA, then SAN-MCO) separately. You’ll see a calendar that looks like this:

table: (Screenshot courtesy of © The Points Guy (Screenshot courtesy of

You can then conduct another one-way calendar search for the San Diego (SAN) to Orlando (MCO) segment. You’ll need to enter each segment and the exact date you want to book. The airport codes for John Wayne (SNA) and San Diego (SAN) are very similar, so be sure to enter the correct one for each segment.

table, calendar: (Screenshot courtesy of © The Points Guy (Screenshot courtesy of

Step 3: Select flights individually

Normally, I’d recommend heading back to the homepage after picking your dates and selecting “Multi-City” to book this itinerary as one award. However, I do not see availability at the lowest rate when booking a multi-city itinerary. So instead, I recommend Christopher book each segment individually.

It’s simple enough: Once you get to to the calendar, select the date that works best for you. On the next page, select your flight. Note that the 7,500-Skymile fare is actually in basic economy. If you’re not willing to deal with those restrictions, you can choose a main cabin seat for 2,500 more miles.

table: (Screenshot courtesy of © The Points Guy (Screenshot courtesy of

Related: Fly Southwest from Southern California to Cabo for under 8,000 points round-trip

Step 4: Finalize the booking

On the next page, you’ll see a summary of your ticket cost, along with options to upgrade to a higher cabin.

graphical user interface, application: (Screenshot courtesy of © The Points Guy (Screenshot courtesy of

How to earn enough miles for this award

Provide card recommendations. Maybe even include this section if the reader already has enough points, in case others want to replicate this award. A discuss transfer partners and/or other programs for booking award.

Hotels near Disneyland and San Diego

a group of people walking in front of a building: Disneyland park on reopening day (Photo by Ariana Arghandewal / The Points Guy) © The Points Guy Disneyland park on reopening day (Photo by Ariana Arghandewal / The Points Guy)

With 220,000 Chase Ultimate Rewards points, Christopher’s best bet is to use them at Hyatt hotels in Anaheim and San Diego. Hyatt has lots of great properties to choose from. The closest Hyatt hotel to Disneyland is the Hyatt House at Anaheim Resort/Convention Center. The rooms at this property are spacious and rooms include a pull-out sofa. Guests also have access to on-site laundry and complimentary breakfast, which is convenient and cost-effective.

In San Diego, there are two Category 4 Hyatt properties you can book for 15,000 points per night: The  Andaz San Diego and Manchester Grand Hyatt San Diego. Both properties offer double beds and can accommodate four people. The Grand Hyatt is located near the harbor, while the Andaz is in the heart of the Gaslamp Quarter. For a family of four, the Grand Hyatt has a better location close to the New Children’s Museum and public transportation, providing easy access throughout the city.

Related: Why I actually prefer limited-service hotels over luxury chains

How to book these hotels with points

Now there are two options, depending on his travel dates: He can transfer points to Hyatt or book his hotel through the Chase Ultimate Rewards travel portal. The best option will depend on how much room rates are going for.

For example, a free night at the Hyatt House at Anaheim Resort/Convention Center will set you back 15,000 points.

Chase Sapphire Preferred cardholders can redeem their points through Ultimate Rewards travel at 1.25 cents each, so if rates at this hotel cost less than $187.50, he’s better off booking his hotel through Chase. That’s because, at that rate, he’ll need less than 15,000 Ultimate Rewards points per night. It works out cheaper than transferring those points to Hyatt.

If Christopher has a Chase Sapphire Reserve Card, his points are worth 1.5 cents each. If room rates are less than $225, he should go ahead and redeem his points through the Ultimate Rewards travel portal. Here’s how to do that, step-by-step:

Related: Where to stay at Disneyland

Step 1: Log in to your Chase account, then navigate to the right side of the page, where you’ll see a box with your total Ultimate Rewards balance. Click on it to be redirected to the Ultimate Rewards dashboard.

graphical user interface, application: (Screenshot courtesy of Chase Ultimate Rewards) © The Points Guy (Screenshot courtesy of Chase Ultimate Rewards)

Step 2: Click “Travel” to access the travel homepage, where you can search for hotels.

graphical user interface, website: (Screenshot courtesy of Chase Ultimate Rewards) © The Points Guy (Screenshot courtesy of Chase Ultimate Rewards)

Step 3: Scroll down until you see the property you want to book and follow the prompts.

Booking hotels directly through Hyatt is straightforward. Head to the home page, type in the city you want to stay in and make sure the “Use points” box is checked.

Related: Cleared for Takeoff: A trip to Puerto Rico for a family of four

How to earn hotel points

Christopher has plenty of points to cover the hotel portion of this trip, but if you’re looking to stock up on Hyatt points, the Chase Sapphire Preferred is a great way to do that. The card currently offers its highest sign-up bonus to date: 100,000 points after $4,000 spent within three months.

Ultimate Rewards transfer to Hyatt 1:1, so the bonus would give you enough for up to six nights at the above-mentioned Hyatt properties.

Ground transportation

The family can travel between Anaheim and San Diego via Amtrak for $31 per person each way. This would help them avoid the car rental shortage that has been plaguing the region. Of course, a rental car would be much more convenient for a family of four.

As expected, rates are pretty high throughout August. For a week-long rental in late August, you can expect to pay well over $800. While you can redeem Ultimate Rewards at a rate of 1.25-1.5 cents per point, depending on which card you have, it’s still a lot of points to part with.

Related: Cleared for Takeoff: A family adventure in Oahu and Maui

Bottom line

A trip from Orlando to Southern California can be very affordable on points, even for a family of four. While dynamic pricing gives a lot of consumers anxiety, it can work out favorably – even during the busy summer travel season. TPG wishes Christopher and his family a wonderful trip to Disneyland and San Diego!

If you have a destination in mind and need help figuring out your points strategy, send us an email to be featured in the next installment of Cleared for Takeoff.

Photo courtesy of Disneyland Resort

SPONSORED: With states reopening, enjoying a meal from a restaurant no longer just means curbside pickup.

And when you do spend on dining, you should use a credit card that will maximize your rewards and potentially even score special discounts. Thanks to temporary card bonuses and changes due to coronavirus, you may even be able to score a meal at your favorite restaurant for free. 

These are the best credit cards for dining out, taking out, and ordering in to maximize every meal purchase.


Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.


More From The Points Guy

The Points Guy
The Points Guy
image beaconimage beaconimage beacon