$46 Cheap Flights from Chicago (MDW) to Orlando (MCO)

View $46 flight on Sat, Oct 18, 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 $46 for one-way flights and $68 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Oct 25 - Sat, Nov 1
MDW
Chicago
MCO
Orlando
$68 Roundtrip, found 3 hours ago
$68
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Chicago to Orlando, returning Sat, Nov 1, priced at $68 found 3 hours ago
Frontier Airlines
Mon, Oct 20 - Sat, Oct 25
MDW
Chicago
MCO
Orlando
$71 Roundtrip, found 5 hours ago
$71
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Chicago to Orlando, returning Sat, Oct 25, priced at $71 found 5 hours ago
Frontier Airlines
Sat, Oct 18 - Thu, Oct 23
MDW
Chicago
MCO
Orlando
$72 Roundtrip, found 2 hours ago
$72
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Chicago to Orlando, returning Thu, Oct 23, priced at $72 found 2 hours ago
Frontier Airlines
Mon, Oct 27 - Sat, Nov 1
MDW
Chicago
MCO
Orlando
$88 Roundtrip, found 8 hours ago
$88
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, Oct 27 from Chicago to Orlando, returning Sat, Nov 1, priced at $88 found 8 hours ago
Frontier Airlines
Fri, Oct 24 - Sat, Nov 8
MDW
Chicago
MCO
Orlando
$89 Roundtrip, found 17 hours ago
$89
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Chicago to Orlando, returning Sat, Nov 8, priced at $89 found 17 hours ago
Frontier Airlines
Sun, Nov 9 - Thu, Nov 13
MDW
Chicago
MCO
Orlando
$92 Roundtrip, just found
$92
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Nov 9 from Chicago to Orlando, returning Thu, Nov 13, priced at $92 just found
Frontier Airlines
Sat, Oct 4 - Thu, Oct 16
MDW
Chicago
MCO
Orlando
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Oct 4 from Chicago to Orlando, returning Thu, Oct 16, priced at $99 found 2 days ago
Frontier Airlines
Sat, Nov 1 - Mon, Dec 1
MDW
Chicago
MCO
Orlando
$112 Roundtrip, found 15 hours ago
$112
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Nov 1 from Chicago to Orlando, returning Mon, Dec 1, priced at $112 found 15 hours ago
Southwest Airlines
Mon, Oct 27 - Sat, Nov 1
MDW
Chicago
MCO
Orlando
$123 Roundtrip, found 8 hours ago
$123
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to Orlando, returning Sat, Nov 1, priced at $123 found 8 hours ago
Delta
Wed, Oct 22 - Sat, Oct 25
MDW
Chicago
MCO
Orlando
$124 Roundtrip, found 4 hours ago
$124
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Oct 22 from Chicago to Orlando, returning Sat, Oct 25, priced at $124 found 4 hours ago

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

February is typically the cheapest month to fly

From $84 - $478 per traveler.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) cost?
Snag a cheap one-way flight from $46 or cheap return flight from $68 from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
The cheapest month to fly from MDW to MCO is October, when demand is low. Off-peak months are usually when you'll find lower airfares between these airports.
Which airlines fly direct from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
Hop on a nonstop flight with Southwest Airlines and head straight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
The cheapest airline to offer flights between Midway Intl. Airport (MDW) and Orlando Intl. Airport (MCO) will change depending on when you plan to fly. Frontier Airlines and Southwest Airlines are just some well-known options offering reasonable prices. Use Expedia's search tool to compare airlines in one place and find the right MDW to MCO flight for your budget.
How many flights per day from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
When flying out of Midway Intl. Airport (MDW), you can pick from an average of 6 daily direct flights to Orlando Intl. Airport (MCO).
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
The 3 PM departures from MDW to MCO are the top choice for many travelers. They can also be more expensive. If you want to save money, choose a less crowded time to fly.
What day of the week has the most flights from MDW to MCO?
Friday has the most flights from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO). Consider taking off on this day and you'll have the best chance of finding a schedule that works for you.
What is the earliest flight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
The first flight of the day taking off from Midway Intl. Airport (MDW) is at around 5:35AM UTC-6. Board this plane and you'll arrive at Orlando Intl. Airport (MCO) at approximately 9:20AM UTC-5. The overall travel time is 2h 45m.
How long does it take to fly from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
It takes about 2 hours and 40 minutes to fly the 990 mi from MDW to MCO.
What is the best time to fly from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) route, travel before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Orlando from Midway Intl. Airport (MDW)?
Check out your flight options from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO). This is the only airport in Orlando you can touch down at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) last-minute?
Booking your flight from MDW to MCO just before your getaway is generally more expensive. But if you're flexible with your schedule, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to MCO flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to MCO flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place will take the stress out of travel planning. Just secure your flights and select from our wide range of hotels, then personalize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO)?
You can usually cancel or reschedule your MDW to MCO flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Orlando Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$67
Distance
991 mi
Average flight time
3 hours 36 mins

Book with confidence

Book with confidence

Chicago to Orlando Flights

The cheapest times to fly from Chicago to Orlando

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Orlando are during the month of October. You can find some of the cheapest flights from Chicago to Orlando with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Orlando

Sunday is one of the best days to book for cheap flights from Chicago to Orlando: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Orlando

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Orlando in 2025. You can also book with separate airlines for your outbound and return journeys, from $46 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Orlando flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Orlando airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Orlando Flights

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