€95 Cheap Flights Chicago to Orlando (MDW-MCO)

Featured airlines

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 15% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap flights from Chicago to Orlando (MDW-MCO)

Prices were available within the past 7 days and start at €95 for one-way flights and €209 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 11 Mar - Wed, 19 Mar
MDW
Chicago
MCO
Orlando
€209 Return, found 6 days ago
€209
Return
found 6 days ago
Select Delta flight, departing Tue, 11 Mar from Chicago to Orlando, returning Wed, 19 Mar, priced at €209 found 6 days ago
Delta
Tue, 11 Mar - Wed, 19 Mar
MDW
Chicago
MCO
Orlando
€216 Return, found 6 days ago
€216
Return
found 6 days ago
Select Delta flight, departing Tue, 11 Mar from Chicago to Orlando, returning Wed, 19 Mar, priced at €216 found 6 days ago
Delta
Sat, 22 Feb - Tue, 25 Feb
MDW
Chicago
MCO
Orlando
€273 Return, found 6 days ago
€273
Return
found 6 days ago
Select Delta flight, departing Sat, 22 Feb from Chicago to Orlando, returning Tue, 25 Feb, priced at €273 found 6 days ago
Delta
Tue, 11 Mar - Wed, 19 Mar
MDW
Chicago
MCO
Orlando
€276 Return, found 6 days ago
€276
Return
found 6 days ago
Select Delta flight, departing Tue, 11 Mar from Chicago to Orlando, returning Wed, 19 Mar, priced at €276 found 6 days ago
Delta
Tue, 11 Mar - Wed, 19 Mar
MDW
Chicago
MCO
Orlando
€278 Return, found 6 days ago
€278
Return
found 6 days ago
Select Delta flight, departing Tue, 11 Mar from Chicago to Orlando, returning Wed, 19 Mar, priced at €278 found 6 days ago
Delta
Tue, 11 Mar - Wed, 19 Mar
MDW
Chicago
MCO
Orlando
€284 Return, found 6 days ago
€284
Return
found 6 days ago
Select Delta flight, departing Tue, 11 Mar from Chicago to Orlando, returning Wed, 19 Mar, priced at €284 found 6 days ago
Delta
Tue, 11 Mar - Wed, 19 Mar
MDW
Chicago
MCO
Orlando
€285 Return, found 6 days ago
€285
Return
found 6 days ago
Select Delta flight, departing Tue, 11 Mar from Chicago to Orlando, returning Wed, 19 Mar, priced at €285 found 6 days ago
Delta
Sat, 22 Feb - Tue, 25 Feb
MDW
Chicago
MCO
Orlando
€343 Return, found 6 days ago
€343
Return
found 6 days ago
Select Delta flight, departing Sat, 22 Feb from Chicago to Orlando, returning Tue, 25 Feb, priced at €343 found 6 days ago
Delta
Tue, 4 Mar - Sat, 8 Mar
MDW
Chicago
MCO
Orlando
€353 Return, found 19 hours ago
€353
Return
found 19 hours ago
Select Delta flight, departing Tue, 4 Mar from Chicago to Orlando, returning Sat, 8 Mar, priced at €353 found 19 hours ago
Delta
Sat, 22 Feb - Tue, 25 Feb
MDW
Chicago
MCO
Orlando
€382 Return, found 6 days ago
€382
Return
found 6 days ago
Select Delta flight, departing Sat, 22 Feb from Chicago to Orlando, returning Tue, 25 Feb, priced at €382 found 6 days ago
Chicago to Orlando route information
Origin airport
Midway Intl.
Destination airport
Orlando Intl.
Airlines serving
Delta
Return price
€208
Distance
1585 km

Perfect flights from Chicago to Orlando

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Orlando. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of Orlando, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Midway Intl. to Orlando Intl. ticket options cater to your travel preferences, with incredible one-way fares from €95 and roundtrip prices from €209. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Orlando Intl. and explore Orlando and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your MDW to MCO travel arrangements today and embark on the journey of a lifetime in Orlando.

Frequently asked questions

How much is a flight from Midway Intl. Airport (MDW) to MCO?
If you’re travelling between Chicago Airport and Orlando Intl. Airport (MCO), round-trip journeys start from €209. 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 kilometres. Set up a playlist of your favourite tunes before you leave home to keep yourself entertained during the trip.
Which airlines fly direct from Chicago Airport to MCO?
Many travellers 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.
*Available to Expedia members.