$60 Cheap Flights from Orlando (MCO) to Chicago (MDW)

View $60 flight on Sat, Jun 7, 2025Opens in a new window
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Cheap Flights from Orlando to Chicago (MCO-MDW)

Prices were available within the past 7 days and start at $60 for one-way flights and $120 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jun 7 - Sat, Jun 14
MCO
Orlando
MDW
Chicago
$120 Roundtrip, just found
$120
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 7 from Orlando to Chicago, returning Sat, Jun 14, priced at $120 just found
Frontier Airlines
Sat, Aug 2 - Sat, Aug 9
MCO
Orlando
MDW
Chicago
$128 Roundtrip, found 3 hours ago
$128
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Aug 2 from Orlando to Chicago, returning Sat, Aug 9, priced at $128 found 3 hours ago
Frontier Airlines
Sat, Jun 7 - Mon, Jun 9
MCO
Orlando
MDW
Chicago
$129 Roundtrip, just found
$129
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 7 from Orlando to Chicago, returning Mon, Jun 9, priced at $129 just found
Frontier Airlines
Fri, Jul 18 - Sat, Jul 26
MCO
Orlando
MDW
Chicago
$133 Roundtrip, found 5 hours ago
$133
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Orlando to Chicago, returning Sat, Jul 26, priced at $133 found 5 hours ago
Frontier Airlines
Mon, Jun 9 - Sat, Jun 14
MCO
Orlando
MDW
Chicago
$137 Roundtrip, found 6 hours ago
$137
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Orlando to Chicago, returning Sat, Jun 14, priced at $137 found 6 hours ago
Frontier Airlines
Thu, Jun 5 - Sun, Jun 15
MCO
Orlando
MDW
Chicago
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jun 5 from Orlando to Chicago, returning Sun, Jun 15, priced at $138 just found
Frontier Airlines
Mon, Jun 9 - Fri, Jun 13
MCO
Orlando
MDW
Chicago
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Jun 9 from Orlando to Chicago, returning Fri, Jun 13, priced at $139 just found
Frontier Airlines
Thu, Jul 10 - Sat, Jul 12
MCO
Orlando
MDW
Chicago
$141 Roundtrip, found 2 days ago
$141
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jul 10 from Orlando to Chicago, returning Sat, Jul 12, priced at $141 found 2 days ago
Delta
Sat, May 24 - Sat, May 31
MCO
Orlando
MDW
Chicago
$160 Roundtrip, found 4 hours ago
$160
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, May 24 from Orlando to Chicago, returning Sat, May 31, priced at $160 found 4 hours ago
Southwest Airlines
Wed, Aug 6 - Sat, Aug 9
MCO
Orlando
MDW
Chicago
$163 Roundtrip, found 3 hours ago
$163
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Aug 6 from Orlando to Chicago, returning Sat, Aug 9, priced at $163 found 3 hours ago

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 $118 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 May 9 2025 and touching down at MDW. The price was last updated on April 23 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 $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MCO on June 7 2025. Prices were last updated on April 23 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.
*Available to One Key members.