Cleared for Takeoff: A budget-friendly family trip to Disneyland and San Diego
This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.
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.
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!
For more TPG news delivered each morning to your inbox, sign up for our free daily newsletter!
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 Southern California
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:
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.
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.
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.
Hotels near Disneyland and San Diego
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.
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.
Step 2: Click “Travel” to access the travel homepage, where you can search for hotels.
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.
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.
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.
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
Welcome to The Points Guy!
Earn 90,000 bonus miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new card in the first three months of card membership. Offer ends 11/10/2021.
With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.
- Limited Time Offer: Earn 90,000 Bonus Miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new Card in your first 3 months. Offer expires 11/10/2021.
- Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
- Earn 3X Miles on Delta purchases and purchases made directly with hotels.
- Earn 2X Miles at restaurants worldwide, including takeout and delivery and at U.S. supermarkets.
- Earn 1X Miles on all other eligible purchases.
- Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. *Payment of the government imposed taxes and fees of no more than $75 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
- Enjoy your first checked bag free on Delta flights.
- Fee Credit for Global Entry or TSA Pre✓®.
- Enjoy an exclusive rate of $39 per person per visit to enter the Delta Sky Club® for you and up to two guests when traveling on a Delta flight.
- No Foreign Transaction Fees.
- $250 Annual Fee.
- Terms Apply.
- See Rates & Fees