Skip to content

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

June 22, 2021
9 min read
Disneyland face masks
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.

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!
Thanks,
Christopher Kellough

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

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 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.

Sign up for our daily newsletter

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:

(Screenshot courtesy of Delta.com)

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.

(Screenshot courtesy of Delta.com)

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.

(Screenshot courtesy of Delta.com)

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.

(Screenshot courtesy of Delta.com)

Hotels near Disneyland and San Diego

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.

(Screenshot courtesy of Chase Ultimate Rewards)

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

(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 60,000 bonus points after you spend $4,000 on purchases in the first three months from account opening.

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

Featured image by You'll wear face coverings while visiting Disneyland. (Photo courtesy of Disneyland Resort)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Top offers from our partners

How we chose these cards

Our points-obsessed staff uses a plethora of credit cards on a daily basis. If anyone on our team wouldn’t recommend it to a friend or a family member, we wouldn’t recommend it on The Points Guy either. Our opinions are our own, and have not been reviewed, approved, or endorsed by our advertising partners.
See all best card offers

TPG featured card

Best for the well-traveled foodie
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review
Apply for American Express® Gold Card
at American Express's secure site

Rewards

3 - 4X points
4XEarn 4X Membership Rewards® Points at Restaurants, plus takeout and delivery in the U.S.
4XEarn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per calendar year in purchases, then 1X).
3XEarn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.

Intro offer

60,000 bonus points
Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.

Annual Fee

$250

Recommended Credit

670-850
Excellent/Good
Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

Why We Chose It

There's a lot to love about the Amex Gold card. It's been a fan favorite during the pandemic because of its fantastic rewards rate on restaurants (that includes takeout and delivery in the U.S.!) and U.S. supermarkets. If you're hitting the skies soon, you'll also earn bonus points on travel. Paired with up to $120 in Uber Cash (for U.S. Uber rides or Uber Eats orders) and up to $120 in annual dining statement credits at eligible partners, there's no reason that the foodie shouldn't add this card to their wallet. Enrollment required.

Pros

  • 4x on dining at restaurants and U.S. supermarkets (on the first $25,000 in purchases per calendar year; then 1x)
  • 3x on flights booked directly with the airline or with Amex Travel
  • Welcome bonus of 60,000 points after spending $4,000 in the first six months

Cons

  • Weak on travel outside of flights and everyday spending bonus categories
  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber/food credits
  • Few travel perks and protections
  • Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.
  • Earn 4X Membership Rewards® Points at Restaurants, plus takeout and delivery in the U.S., and earn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per calendar year in purchases, then 1X).
  • Earn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and each month automatically get $10 in Uber Cash for Uber Eats orders or Uber rides in the U.S., totaling up to $120 per year.
  • $120 Dining Credit: Satisfy your cravings and earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, Milk Bar and select Shake Shack locations. Enrollment required.
  • Choose the color that suits your style. Gold or Rose Gold.
  • No Foreign Transaction Fees.
  • Annual Fee is $250.
  • Terms Apply.
  • See Rates & Fees
Apply for American Express® Gold Card
at American Express's secure site
Terms & restrictions apply. See rates & fees
Best for the well-traveled foodie
TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
4 / 5
Go to review

Rewards Rate

4XEarn 4X Membership Rewards® Points at Restaurants, plus takeout and delivery in the U.S.
4XEarn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per calendar year in purchases, then 1X).
3XEarn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
  • Intro Offer
    Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.

    60,000 bonus points
  • Annual Fee

    $250
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    670-850
    Excellent/Good

Why We Chose It

There's a lot to love about the Amex Gold card. It's been a fan favorite during the pandemic because of its fantastic rewards rate on restaurants (that includes takeout and delivery in the U.S.!) and U.S. supermarkets. If you're hitting the skies soon, you'll also earn bonus points on travel. Paired with up to $120 in Uber Cash (for U.S. Uber rides or Uber Eats orders) and up to $120 in annual dining statement credits at eligible partners, there's no reason that the foodie shouldn't add this card to their wallet. Enrollment required.

Pros

  • 4x on dining at restaurants and U.S. supermarkets (on the first $25,000 in purchases per calendar year; then 1x)
  • 3x on flights booked directly with the airline or with Amex Travel
  • Welcome bonus of 60,000 points after spending $4,000 in the first six months

Cons

  • Weak on travel outside of flights and everyday spending bonus categories
  • Not as useful for those living outside the U.S.
  • Some may have trouble using Uber/food credits
  • Few travel perks and protections
  • Earn 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of Card Membership.
  • Earn 4X Membership Rewards® Points at Restaurants, plus takeout and delivery in the U.S., and earn 4X Membership Rewards® points at U.S. supermarkets (on up to $25,000 per calendar year in purchases, then 1X).
  • Earn 3X Membership Rewards® points on flights booked directly with airlines or on amextravel.com.
  • $120 Uber Cash on Gold: Add your Gold Card to your Uber account and each month automatically get $10 in Uber Cash for Uber Eats orders or Uber rides in the U.S., totaling up to $120 per year.
  • $120 Dining Credit: Satisfy your cravings and earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, Milk Bar and select Shake Shack locations. Enrollment required.
  • Choose the color that suits your style. Gold or Rose Gold.
  • No Foreign Transaction Fees.
  • Annual Fee is $250.
  • Terms Apply.
  • See Rates & Fees