$99 Cheap Delta flights Chicago (MDW) to Orlando (MCO)

View $99 flight on Wed, Aug 27, 2025Opens in a new window

  • 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 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

$99 Cheap Delta flights Chicago (MDW) to Orlando (MCO)

Prices were available within the past 7 days and start at $99 for one-way flights and $155 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Nov 10 - Thu, Nov 13
MDW
Chicago
MCO
Orlando
$155 Roundtrip, found 1 hour ago
$155
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Nov 10 from Chicago to Orlando, returning Thu, Nov 13, priced at $155 found 1 hour ago
Flights from Chicago (MDW) to Orlando (MCO)
Origin airport
Midway Intl.
Destination airport
Orlando Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Popular airline
Delta
Distance
991 mi
Average flight time
3 hours 38 mins

Frequently asked questions

How much is a Delta Air Lines flight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
Apply the "Price (lowest to highest)" filter on Expedia to find cheap Delta Air Lines return flights from $155 from MDW to MCO. Affordable one-way fares from $99 are available as well.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from MDW to MCO with Delta Air Lines?
Look for one-way or round-trip flights to Orlando in September or October. You could find cheaper fares with Delta Air Lines during these off-peak times.
What is the cheapest time to book flights from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) with Delta Air Lines?
Search for affordable Delta Air Lines flights from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) one to three months before your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. No matter the fare class and journey, the best day of the week to book a domestic flight is generally Sunday and the most expensive tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does Delta Air Lines fly nonstop from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
Select our "Nonstop" filter when browsing for direct Delta Air Lines flights from MDW to MCO. It's also a good way to compare other carriers offering the same nonstop journey.
What is the earliest Delta Air Lines flight from MDW to MCO?
Search Delta Air Lines's earliest flights from MDW to MCO by selecting our "Morning" and "Early Morning" filters. Not only will you get to your destination sooner, early departures also experience 20% fewer cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Delta Air Lines fly into in Orlando?
Orlando Intl. Airport (MCO) is the primary Orlando gateway for Delta Air Lines flights from Midway Intl. Airport (MDW).
Why fly with Delta Air Lines from MDW to MCO?
Jetting off from MDW to MCO with Delta Air Lines comes with a range of perks, such as a rewarding loyalty program and an excellent in-flight experience. Plus, when booking through Expedia, One Key™ members can earn OneKeyCash™* to spend on select future travel purchases. That's in addition to the Delta SkyMiles points you can earn with Delta Air Lines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Delta Air Lines flight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
You can usually cancel or reschedule your flight, although there may be a charge if you made your booking over 24 hours ago. Want to keep your options open? Make use of our "Changes included" or "No cancel fee" filter to find flights that won't charge you extra if you need to alter your plans. To modify your booking, head to "Trips," select your flight and click on "Manage Booking" for more details.

Explore a world of travel with Expedia

*Available to One Key members.