The cheapest flight to Orlando in our 28 October 2026 check was $267 round trip from New York on Frontier, with one stop. A Frontier nonstop cost just $7 more at $274. Chicago came in at $354 and Boston at $383.
We priced the same week, 12 to 19 December 2026, from three of the biggest Orlando markets. New York was the cheapest by a clear margin, and it also had the most choice: our search there returned 320 itineraries, against 93 from Boston.
The nonstop column is the one to read. On all three routes a nonstop cost little or nothing more than the cheapest fare.
| Flying from | Lowest round trip | Lowest nonstop |
|---|---|---|
| New York (NYC) | $267 on Frontier, 1 stop | $274 on Frontier |
| Chicago (CHI) | $354 on Southwest, nonstop | $354 on Southwest |
| Boston (BOS) | $383 on Southwest, 1 stop | $399 on Southwest |
Travel 12 to 19 December 2026, all into Orlando International (MCO). Round trip, economy, one adult, taxes included. Fares change daily, so check the live search above for your own dates.
On these numbers, yes, every time. From New York the Frontier nonstop was $7 dearer than the one-stop and took about 3 hours, while the cheapest connection took 6 hours 40 minutes. Seven dollars for more than three and a half hours back is an easy call.
From Boston the gap was $16, $399 nonstop against $383 with a stop. From Chicago there was no gap at all: the lowest fare was already a Southwest nonstop.
Read the bag rules before you pick the $267 or $274 Frontier fare. Frontier's base fare includes one free personal item that fits under the seat, and a full-size carry-on costs extra unless you buy a bundle.
Southwest, which had the lowest fares from Chicago and Boston, includes a carry-on on every fare. If you're packing for a week at the parks, add Frontier's carry-on charge to its fare before you compare it with anything else.
All three of our checks were into Orlando International (MCO), the main airport southeast of downtown and the one most airlines use. Orlando Sanford (SFB) is a different airport, a long way north, served by a smaller set of airlines.
If your hotel is near the theme parks, MCO is the closer arrival. Before you pay for any Orlando fare, look at the arrival code, because a cheap seat into SFB can come with a much longer drive.
From New York the Frontier nonstop in our check was scheduled at 182 minutes, so a little over 3 hours. From Chicago the Southwest nonstops ran 150 to 160 minutes.
New York and Boston are on the same Eastern time as Orlando. Chicago is an hour behind, so you lose an hour flying down.
We don't have enough of our own checks yet to tell you the cheapest week of the year, and we'd rather say that than guess. These numbers cover one December week, just before the school holidays.
Orlando prices follow school calendars, so if your dates are flexible, try a week either side in the search above. Fares change daily, so check again a few days later before you book.
In our 28 October 2026 check, round trips for 12 to 19 December 2026 started at $267 from New York, $354 from Chicago and $383 from Boston, taxes included. All three were into Orlando International (MCO). Fares change daily and vary by city and date, so run your own search above and treat these as real figures from one check.
New York, by a wide margin. Our 28 October 2026 search found $267 round trip on Frontier with one stop, and a Frontier nonstop at $274. Chicago's lowest was $354 and Boston's was $383 for the same week. A bigger market usually means more airlines competing, and New York returned 320 itineraries against Boston's 93.
Yes. Our 28 October 2026 check found a Frontier nonstop from New York at $274 round trip, scheduled at 182 minutes. That was only $7 more than the cheapest fare, a one-stop trip on the same airline. Check which New York airport the flight leaves from before you book, since our search covered all of them.
Not on Frontier, which had the cheapest fares from New York. Frontier includes one free personal item, and a full-size carry-on costs extra unless your bundle includes one. Southwest, cheapest from Chicago and Boston in our check, includes a carry-on on every fare, so compare the total with bags before you choose.
Orlando International (MCO) for most trips. MCO is the main airport, served by most airlines, and much closer to the theme parks than Orlando Sanford (SFB), which sits well north of the city. Our fare checks were all into MCO, so if you see a cheaper fare into SFB, add the extra drive before deciding.
About 2 and a half hours. The Southwest nonstops from Chicago in our 28 October 2026 check were scheduled at 150 to 160 minutes, at $354 round trip. Orlando is an hour ahead of Chicago, so you lose an hour on the way down and get it back flying home.
About this page
Written and fact-checked by the Flyingscanner team, last updated 28 October 2026. The fares quoted here come from our own live search on 28 October 2026, not estimates. Fares change until the airline issues a ticket, so check the live search on this page before you book. How Flyingscanner checks fares
