₩207,500 Cheap Flights from Chicago (MDW) to Orlando (MCO)

View ₩207,500 flight on Sat, Oct 11, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Orlando Intl. Airport (MCO)

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Cheap Flights from Chicago to Orlando (MDW-MCO)

Prices were available within the past 7 days and start at ₩207,500 for one-way flights and ₩414,900 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 11 - Sun, Oct 12
MDW
Chicago
MCO
Orlando
₩414,900 Roundtrip, found 4 days ago
₩414,900
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 11 from Chicago to Orlando, returning Sun, Oct 12, priced at ₩414,900 found 4 days ago
Delta
Sat, Oct 11 - Sun, Oct 12
MDW
Chicago
MCO
Orlando
₩498,100 Roundtrip, found 4 days ago
₩498,100
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 11 from Chicago to Orlando, returning Sun, Oct 12, priced at ₩498,100 found 4 days ago
Delta
Sat, Oct 11 - Sun, Oct 12
MDW
Chicago
MCO
Orlando
₩581,400 Roundtrip, found 4 days ago
₩581,400
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 11 from Chicago to Orlando, returning Sun, Oct 12, priced at ₩581,400 found 4 days ago

Find the cheapest month to fly from Chicago (MDW) to Orlando (MCO)

February is typically the cheapest month to fly

From ₩117,063 - ₩663,891 per traveler.

Frequently asked questions

How much is a flight from Midway Intl. Airport (MDW) to MCO?
If you're traveling between Chicago Airport and Orlando Intl. Airport (MCO), round-trip journeys start from ₩414,900. This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year, so don't delay. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Midway Airport to Orlando Intl. Airport (MCO)?
We understand that things crop up unexpectedly, so we've made it as simple as possible for you to cancel your flight online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from Midway Intl. Airport (MDW) to Orlando Intl. Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Chicago Airport to Orlando Intl. Airport flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
Recline your seat, pick an in-flight movie and 2 hours and 34 minutes will pass by in a jiffy. That's how long it takes to fly to Orlando Intl. Airport (MCO) from MDW (MDW).
How far is the flight from Chicago Airport to Orlando Intl. Airport (MCO)?
You'll be soaring through the sky for a while, as the flight distance from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) is 1,600 kilometers. Set up a playlist of your favorite tunes before you leave home to keep yourself entertained during the trip.
Which airlines fly direct from Chicago Airport to MCO?
Many travelers like to fly with Southwest Airlines (WN) from Midway Airport to MCO. This leading airline offers 217 flights every month, so you can easily find a flight time that's right for you. Another airline operating on this route is Frontier Airlines (F9). You'll have 52 flights each month to choose from.
Are MDW to Orlando Intl. Airport flight tickets cheaper when they're purchased at the last minute?
Airline tickets from Midway Intl. Airport (MDW) to Orlando Intl. Airport are available up to a year before departure on Expedia. And although you may pick up a fantastic last-minute deal, it's never something you can count on. Also, booking your flights ahead of time means you'll have more choices — and you can avoid getting caught in the dreaded middle seat! We frequently update our fares to make sure you get the biggest bargains, so keep checking in for all the latest specials.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Orlando Intl.
Roundtrip price
₩414,900
Distance
1585 km
Average flight time
3 hours 36 mins

Book with confidence

Book with confidence

Chicago to Orlando Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Orlando will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Orlando.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with MDW to MCO flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MCO with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Chicago to Orlando Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

O'Hare Intl. to Orlando
₩272,000
*Available to Expedia members.