I love traveling to Disney World, but I hate paying a lot to fly to Florida.
I have a motto: I will never pay $500 to fly somewhere in the United States. If it is domestic, I’ll find a deal.
Don’t believe me? I just got a deal for under $250 (with trip insurance) to fly to Disney in November.
For those not in the know, the first week of November is aptly called Jersey Week in Disney World because N.J. residents flock to Florida during the teachers’ convention.
So, getting a flight for $216 that week is practically unheard of. Let me tell you how I did it.
How to score a good flight deal
Now, a bunch of TikTok videos will tell you how they got a major “deal” on a flight, and then the deal is just that they used their airline points. That’s not what happened here. I did not use any points to score this deal.
But I am a United MileagePlus member, so I earned points by booking this flight. I also have a United MilePlus Explorer credit card. That means that I get priority boarding and my first checked bag is free (both ways) – not that I ever check a bag, thanks to my Beis travel backpack + Away Carry-On power combo.
I didn’t have to give up my favorite airlines, United and JetBlue, either, to go with a budget airline like Spirit Airlines or Frontier. I don’t need to drive 90 minutes to New York to fly out of JFK or LGA, either. I am traveling right out of Newark, baby.
Flight details
Wednesday, 11/5 – 6 a.m. – EWR to MCO for $108
Monday, 11/10 – 3:30 p.m. – MCO to EWR for $108
That’s only $216 round-trip from New Jersey to Orlando during a peak season, AKA one of the busiest months of the year to fly. I tacked on $14 trip insurance (each way), so my total came to just under $250, because Newark Airport had a tumultuous run earlier this year, and I am not chancing anything.
So, how did I do it? Here are my top two tips.
Price watching
Booking one-way tickets
If I am traveling anywhere, the first thing I do is log into Hopper and put my flight dates in to see if the website predicts that the flight costs will increase or decrease. If it says prices will decrease, I start heavily monitoring all the travel sites. I stalked them all. I was frequently on Expedia, United, Delta and JetBlue’s websites. Sometimes, I will spend weeks watching prices. Just a week ago, that same flight was $400+ on United.
Secondly, I never book a round-trip flight anywhere. I fully believe booking a one-way ticket is always cheaper than booking a round-trip ticket, from my experience. I sometimes do this to mix and match airlines, as one airline might be cheaper going, but not that cheap returning, whereas a different airline will be cheaper returning than they are going. I still book a round-trip experience, I just do it by booking two one-way tickets separately.
I’ve often booked United and JetBlue together to mix and match these lower fares. But this time, it worked out that United was the cheapest and best option, both flying out of EWR into MCO and then coming back from MCO to EWR.
When is the best time to book a flight?
As we’ve previously reported, the best time to book a flight, as far as domestic travels go, is at least 30-45 days in advance. I booked my flight about 50 days before my trip, so I was getting down to the wire on that window when the prices would start to increase.
According to Executive Editor, Kyle Potter, of the Thrifty Traveler, “Typically, Tuesday, Wednesday or Saturday” are the cheapest days to fly and “the best days to fly – both for a lower cost and a less-hectic airport experience.”
This aligned with one of my travel dates, but not both, actually. I am flying to Florida on a Wednesday at 6 AM, which is a coveted flight time now, due to trying to avoid delayed flights. And then I am returning home on a Monday, which happens to be a very busy travel day of the week for business professionals.
You know it’s a good deal because I managed to get the exact times I wanted for both of my flights at the cheapest price possible. I have a very early arrival to kick off my Disney trip immediately, and an afternoon departure, so I can enjoy my resort or Disney Springs before I have to leave.
When is Jersey Week?
Jersey Week is the unofficial time of year when N.J. takes over Florida. In fact, according to our friends at KAYAK, 20% of all flight searches by New Jerseyans traveling between Nov. 5-12 (“Jersey Week”) are for trips to Orlando.
The NJEA convention takes place from November 6-7, 2025 this year. New Jersey schools are closed on both days, so many families will take advantage of this and book over that 4-day weekend. This convention also lines up with Veterans Day (November 11), which is also a day that students get off from school.
That means that Jersey Week 2025 is in that timeframe between November 5 and November 12, with heavy park attendance expected between November 6 and 11.
According to KAYAK, more than ⅔ of New Jerseyans (67%) searching for travel during Jersey Week are looking to fly out of EWR. In 2024, EWR was the most expensive airport with an average airfare (one way) of $296 during this same timeframe.
So, if you’re one of those Jersey folks looking to still book your flight to Disney, check out United’s deals page and see if you can follow my tips and tricks to score a flight for under $250.