$55 Cheap Flights from Orlando (MCO) to Chicago (MDW)

View $55 flight on Sat, Aug 2, 2025Opens in a new window

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

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Cheap Flights from Orlando to Chicago (MCO-MDW)

Prices were available within the past 7 days and start at $55 for one-way flights and $106 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Aug 5 - Sat, Aug 16
MCO
Orlando
MDW
Chicago
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Orlando to Chicago, returning Sat, Aug 16, priced at $106 found 4 days ago
Frontier Airlines
Fri, Aug 15 - Sun, Aug 17
MCO
Orlando
MDW
Chicago
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando to Chicago, returning Sun, Aug 17, priced at $110 just found
Frontier Airlines
Tue, Aug 5 - Mon, Aug 11
MCO
Orlando
MDW
Chicago
$116 Roundtrip, found 4 days ago
$116
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Orlando to Chicago, returning Mon, Aug 11, priced at $116 found 4 days ago
Frontier Airlines
Sat, Aug 2 - Wed, Aug 20
MCO
Orlando
MDW
Chicago
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 2 from Orlando to Chicago, returning Wed, Aug 20, priced at $127 found 4 days ago
Frontier Airlines
Thu, Jul 17 - Sat, Jul 19
MCO
Orlando
MDW
Chicago
$129 Roundtrip, found 1 hour ago
$129
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Jul 17 from Orlando to Chicago, returning Sat, Jul 19, priced at $129 found 1 hour ago
Frontier Airlines
Fri, Jul 25 - Sun, Jul 27
MCO
Orlando
MDW
Chicago
$130 Roundtrip, just found
$130
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 25 from Orlando to Chicago, returning Sun, Jul 27, priced at $130 just found
Southwest Airlines
Tue, Aug 26 - Sat, Aug 30
MCO
Orlando
MDW
Chicago
$135 Roundtrip, found 2 hours ago
$135
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Orlando to Chicago, returning Sat, Aug 30, priced at $135 found 2 hours ago
Frontier Airlines
Fri, Aug 15 - Mon, Aug 18
MCO
Orlando
MDW
Chicago
$136 Roundtrip, just found
$136
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Aug 15 from Orlando to Chicago, returning Mon, Aug 18, priced at $136 just found
Frontier Airlines
Sat, Aug 2 - Thu, Aug 21
MCO
Orlando
MDW
Chicago
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 2 from Orlando to Chicago, returning Thu, Aug 21, priced at $137 found 4 days ago
Delta
Thu, Aug 21 - Sun, Aug 24
MCO
Orlando
MDW
Chicago
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Delta flight, departing Thu, Aug 21 from Orlando to Chicago, returning Sun, Aug 24, priced at $154 just found

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

February is typically the cheapest month to fly

From $78 - $279 per traveler.

Graph displaying average flight prices per month

Flights from Orlando (MCO) to Chicago (MDW)
Origin airport
Orlando Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$52
Distance
991 mi
Average flight time
1 hour 50 mins

Orlando to Chicago Flights

The cheapest times to fly from Orlando to Chicago

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 Orlando to Chicago are during the month of August. You can find some of the cheapest flights from Orlando to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Orlando to Chicago

Sunday is one of the best days to book for cheap flights from Orlando to Chicago: 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 Orlando to Chicago

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 Orlando to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $55 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 Orlando to Chicago 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 Orlando to Chicago 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.

 

Frequently asked questions

How much does a flight from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW) cost?
Grab cheap return fares starting from $43 from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Frontier Airlines flight leaving MCO on July 26 2025 and touching down at MDW. The price was last updated on June 29 2025 and has not changed since.
What is the cheapest month to fly from MCO to MDW?
The cheapest flights from MCO to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW)?
If you're departing from Orlando Intl. Airport (MCO), you can hop on a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from MCO to MDW?
At the moment, the cheapest airline offering one-way flights from MCO to MDW is Frontier Airlines. You can take off on this route from $24. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MCO on September 13 2025. Prices were last updated on June 29 2025 and have not changed since.
How many flights per day from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW)?
When taking off from Orlando Intl. Airport (MCO), you can take your pick from an average of 6 daily nonstop flights to Midway Intl. Airport (MDW).
What are the most popular departure times for flights from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW)?
Flights between MCO and MDW are their busiest at 10 AM. For a quieter experience and potentially cheaper prices, look for a time outside the usual busy windows.
What day of the week has the most flights from MCO to MDW?
Fly on a Friday if you're searching for the biggest selection of flights from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW).
What is the earliest flight from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 7:10AM UTC-5, heading out of Orlando Intl. Airport (MCO). You'll be traveling for roughly 2h 55m, coming in to land at Midway Intl. Airport (MDW) at approximately 9:05AM UTC-6.
How long does it take to fly from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW)?
The average flight time from MCO to MDW is 2 hours and 56 minutes, covering a total distance of 990 mi.
What is the best time to fly from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on schedule, opt for a flight that leaves from Orlando Intl. Airport (MCO) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Chicago from Orlando Intl. Airport (MCO)?
Catch a direct flight from Orlando Intl. Airport (MCO) to Chicago and arrive at O'Hare Intl. Airport (ORD). Another convenient entry point into this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from MCO to MDW right before your trip is generally more expensive. But if there's some wiggle room with your schedule, you could score a cheap last-minute fare.
Is it cheaper to book a MCO to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a MCO to MDW flight and hotel package with Expedia could result in significant savings. What's more, managing everything in one place will take the hassle out of travel planning. Simply secure your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Orlando Intl. Airport (MCO) to Midway Intl. Airport (MDW)?
If you booked your MCO to MDW flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

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*Available to One Key members.