If you’ve ever taken the family to Disney World, you know that Disney magic can be hard on any parent’s wallet! But at least you can save (or splurge, if you prefer) on your flights and hotel accommodations with points and miles. 

In this series of blog posts, we show you ways to get to a specific destination, whether you have lots of points or very few. You can choose one strategy or mix and match to make your trip.

For this post, we’re going to look at booking a family of three from the Chicago area for a long weekend in Orlando around Halloween. Luckily, Chicago has lots of direct flight options, so this family trip should be relatively easy to book with different types of points. 

The family will also have lots of hotel options—as all the major hotel programs have various properties in and around Disney World and the greater Orlando area. 

So let’s get to booking! 

 

Low Points Price Flight – American Airlines 

If you have American Airlines miles, you could book for as little as 9,500 miles per person plus $5.60 in taxes, if you’re willing to get to the airport very early. Or it might make sense to take the later flight for only 12,000 miles—still a good deal. 

But this deal gets even better if you have Alaska Airlines Atmos™ Rewards points. Alaska and American are partner airlines, and you can sometimes book American’s flights through Alaska for a better price. In this case, you could book this same flight for as few as 7,500 points per person one way, plus $19 in taxes and fees! 

 

 

Low Points Price Hotel – Residence Inn by Marriott Orlando Lake Buena Vista 

Located just a few miles from Walt Disney World, the Residence Inn by Marriott Orlando Lake Buena Vista is a family-friendly property you can book with your Marriott Bonvoy points. The hotel has a pool, fitness center, laundry (clutch on a family trip), and free breakfast. 

This property charges $26 per day for parking, and it also offers a park shuttle. 

You can book a two-room suite at this property in late October for only 20,000 Marriott Bonvoy points per night. You’d have plenty of space for the family here with two queen beds, a sofa bed, and a kitchen. 

If you can stay for five nights on points (not free-night certificates), you can get one night free—saving even more on this redemption! 

 

 

 

 

Medium Points Price Flight – United  

If you don’t have American miles or Atmos™ Rewards points, you can also book this flight via United for 15,000 miles per person plus taxes. Because Chicago is a United hub, there are lots of flight options to choose from. 

If you’re interested in this flight and don’t have United miles, you can also book this through Air Canada Aeroplan. In this case, it’s the same points price but with higher taxes and fees. Still, this could be a good alternative if you want to save your Chase Ultimate Rewards® or Bilt points for a transfer to another partner like Hyatt or Southwest. If you can book this during a transfer bonus, it can be an even better deal.  

 

 

 

Medium Points Price Hotel – Hyatt Regency Grand Cypress Resort 

The Hyatt Regency Grand Cypress Resort is another family-friendly hotel with a gorgeous, lagoon-style pool to relax in in between visits to the Disney parks. The hotel also offers a lakefront beach with kayaks, paddleboards, and other water activities. Your family can also enjoy an arcade, a fire pit, bike trails, and more. 

One thing to consider is that the property charges for parking (if you’re not a Globalist or staying on a Guest of Honor award). The hotel has a shuttle to the parks and an Uber/Lyft drop-off area, so you’ll want to determine whether it makes sense to rent a car for your trip. 

This property is a Category 4, and as of April 2026, it cost between 12,000 points and 18,000 Hyatt points per night. I found availability here for various nights in October 2026 between 15,000 and 18,000 points per night. Cash prices were more than $300 per night at the time. 

The hotel is a popular choice for using the Hyatt Category 1-4 free-night certificate among members of our Facebook group! While unfortunately Hyatt points prices will be going up this year, your free-night certificates will still work for as long as the property remains in Category 4. 

 

 

High Points Price Flight – Southwest 

Southwest was the most expensive option I found, at 18,500 points one-way for their “Basic” fare. If you have a Companion Pass, this would be a much more affordable option. 

Southwest’s basic fares are like other airlines’ basic economy fares. Basic means you’ll be the last to board, won’t be able to choose your seats, and have less flexibility if you need to cancel. But if you hold a Southwest credit card, you can board earlier, select a seat, and check a bag for free. 

 

 

High Points Price Hotel – Conrad Orlando (Hilton Points) 

If you’re looking to enjoy the beach and Disney, you can spend your Hilton points at the Conrad Orlando. Located near Evermore Bay, the hotel has its own beach and a beautiful pool. 

The hotel also offers a shuttle to Disney parks. You can even get a “grab-and-go” breakfast before you catch the shuttle—ideal for those who like to get in those park lines early! The property charges $50 per night for valet parking (and there is no self-parking). 

I found rooms at this property between 90,000 and 105,000 Hilton points per night for various dates in October. Around the same time, rates were more than $500, so this example would also be a great use of the ultra-valuable Hilton free-night certificate! 

If you can book a longer trip, you could also book five nights and get the fifth night free, if you’re booking your reservation fully on points. You must have Hilton status to get the fifth-night-free benefit. 

Redeem four nights, get the fifth night free when you redeem points for a consecutive five-night Hilton hotel stay. You can receive a fifth Reward Night free, redeemable at that same hotel during that same stay.

 

 

 

Bottom Line

Visiting Orlando can certainly be expensive, but your flights and hotel stays don’t have to break the bank thanks to points and miles! 

 

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