The lowest Chicago to Orlando round trip in our 28 October 2026 check was $354 on Southwest, for travel from 12 to 19 December. It was a nonstop, and so were the next nine fares, each scheduled at 150 to 160 minutes.
From 5 real fares found in our latest check, checked Oct 28, 2026, 6:08 AM EDT. Prices are per person and can change.
Fares shown are the lowest found at the time of the snapshot, per person, and are subject to availability and change at the time of booking.
5 real fares from our latest check, cheapest first. Prices are per person and can change until ticketed.
WN · Southwest Airlines
Nonstop · 2h 30m · Sat, Dec 12
WN · Southwest Airlines
Nonstop · 2h 35m · Sat, Dec 12
WN · Southwest Airlines
Nonstop · 2h 35m · Sat, Dec 12
WN · Southwest Airlines
Nonstop · 2h 40m · Sat, Dec 12
WN · Southwest Airlines
Nonstop · 2h 35m · Sat, Dec 12
We searched Chicago, all airports, to Orlando International for 12 to 19 December 2026. The search came back with 135 itineraries. The 10 lowest cost exactly the same, $354 round trip, all on Southwest, and not one of them stopped on the way.
That makes this an easy route to read. When the top of the list is ten nonstops at one price, you're choosing a departure time, not hunting for a deal.
| What we checked | What we found | What it means for you |
|---|---|---|
| Lowest round trip | $354 on Southwest | The same price covered all 10 of the lowest fares |
| Stops | 0 on the 10 lowest fares | No need to trade hours for a lower price on these dates |
| Scheduled flight time | 150 to 160 minutes | About 2 hours 30 minutes in the air |
| Itineraries returned | 135 | Plenty of choice above the lowest fare |
| Dates searched | 12 to 19 December 2026 | One week's snapshot, so run your own dates |
Round trip, economy, one adult, taxes included. Fares change daily, so check the live search above before you book.
Not on the dates we checked. All 10 of the lowest fares were nonstop, so a stop bought you nothing.
If a one-stop itinerary does show up cheaper on your dates, look at the total journey time before you take it. The nonstop is about 2 hours 30 minutes. A connection usually adds at least an hour or two on the ground, and a missed connection on a holiday weekend is a bad way to start a trip to the parks.
Chicago has two big airports, O'Hare (ORD) and Midway (MDW), and our search covered both under the city code CHI. The fare list doesn't tell us which one each of those Southwest flights left from, so check the departure airport on the flight you pick.
O'Hare sits on the northwest side of the city and Midway on the southwest side. The right one is usually whichever is closer to home, because a cheap seat from the wrong airport costs you an extra hour each way. To price one airport on its own, type ORD to MCO or MDW to MCO into the search above instead of Chicago.
Orlando International (MCO) is the city's main airport and the one our check searched. Orlando Sanford (SFB) is a separate airport well north of the city, with a different set of airlines.
That matters if you're going to the theme parks, which sit south and west of MCO. A fare into SFB can look like a saving until you add the longer drive. Check the arrival code on any fare before you pay.
Plan on about 2 hours 30 minutes in the air. The nonstops in our check were scheduled at 150 to 160 minutes.
Orlando runs on Eastern time, one hour ahead of Chicago. A 9:00 departure from Chicago lands around 12:30 Orlando time, and on the way home you get that hour back. Leave room for security at either Chicago airport, especially on a Friday in December.
We don't have enough of our own checks on this route yet to name a best week to book, and we'd rather say so than guess. What we do know is narrow: one search on 28 October 2026 found $354 for a December week.
Fares change daily. Try two or three sets of dates in the search above, then check again a few days later before you commit.
Our 28 October 2026 check found $354 round trip on Southwest, for travel from 12 to 19 December 2026, with taxes included. All 10 of the lowest fares were that same price and nonstop. Fares change daily and depend on your dates, so run your own search above and treat $354 as one real data point rather than a promise.
Yes. Every one of the 10 lowest fares in our 28 October 2026 check was a nonstop, scheduled at 150 to 160 minutes. On those dates you didn't have to accept a connection to get the lowest fare, which isn't true on every route. Check which Chicago airport your flight leaves from, since the city has both O'Hare and Midway.
Southwest had all 10 of the lowest fares in our 28 October 2026 search, at $354 round trip. That's one search on one set of dates, not a ranking of every airline on the route. Run your own dates in the search above to see which airlines come back, and compare the bag rules as well as the fare.
Pick the airport that's easier for you to reach. O'Hare (ORD) is on the northwest side of Chicago and Midway (MDW) is on the southwest side, so the trip to the airport can matter more than a small fare difference. Enter ORD or MDW in the search above, instead of Chicago, to price one airport on its own.
About 2 hours 30 minutes. The nonstops in our 28 October 2026 check were scheduled at 150 to 160 minutes. Orlando runs one hour ahead of Chicago, so a 9:00 departure lands around 12:30 local time, and on the way home you gain that hour back. Add time for security and the trip to the airport.
No. Orlando International (MCO) is the main airport and the one our check searched. Orlando Sanford (SFB) is a separate airport north of the city with a different set of airlines, so a cheap fare into SFB can mean a much longer drive to the parks. Check the arrival code on any fare before you pay for it.
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
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