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

View $60 flight on Sat, Jun 14, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Orlando (MDW-MCO)

Prices were available within the past 7 days and start at $60 for one-way flights and $128 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Jul 26 - Sat, Aug 2
MDW
Chicago
MCO
Orlando
$128 Roundtrip, found 1 hour ago
$128
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jul 26 from Chicago to Orlando, returning Sat, Aug 2, priced at $128 found 1 hour ago
Frontier Airlines
Fri, Jun 6 - Sat, Jun 7
MDW
Chicago
MCO
Orlando
$129 Roundtrip, found 2 hours ago
$129
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Jun 6 from Chicago to Orlando, returning Sat, Jun 7, priced at $129 found 2 hours ago
Frontier Airlines
Sat, Jun 14 - Thu, Jun 19
MDW
Chicago
MCO
Orlando
$130 Roundtrip, found 3 hours ago
$130
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Chicago to Orlando, returning Thu, Jun 19, priced at $130 found 3 hours ago
Frontier Airlines
Sat, Aug 9 - Thu, Aug 14
MDW
Chicago
MCO
Orlando
$133 Roundtrip, found 3 hours ago
$133
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Aug 9 from Chicago to Orlando, returning Thu, Aug 14, priced at $133 found 3 hours ago
Frontier Airlines
Fri, Jul 18 - Sat, Jul 26
MDW
Chicago
MCO
Orlando
$134 Roundtrip, found 3 hours ago
$134
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Jul 18 from Chicago to Orlando, returning Sat, Jul 26, priced at $134 found 3 hours ago
Frontier Airlines
Mon, May 19 - Fri, May 23
MDW
Chicago
MCO
Orlando
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, May 19 from Chicago to Orlando, returning Fri, May 23, priced at $138 just found
Frontier Airlines
Sun, Jun 15 - Thu, Jun 19
MDW
Chicago
MCO
Orlando
$139 Roundtrip, found 2 hours ago
$139
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Jun 15 from Chicago to Orlando, returning Thu, Jun 19, priced at $139 found 2 hours ago
Frontier Airlines
Mon, Jul 21 - Sat, Aug 2
MDW
Chicago
MCO
Orlando
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jul 21 from Chicago to Orlando, returning Sat, Aug 2, priced at $142 found 1 day ago
Southwest Airlines
Sat, May 24 - Fri, May 30
MDW
Chicago
MCO
Orlando
$159 Roundtrip, just found
$159
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, May 24 from Chicago to Orlando, returning Fri, May 30, priced at $159 just found
Delta
Wed, May 28 - Sat, Jun 7
MDW
Chicago
MCO
Orlando
$169 Roundtrip, found 4 hours ago
$169
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, May 28 from Chicago to Orlando, returning Sat, Jun 7, priced at $169 found 4 hours ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO) cost?
Pick up cheap return fares starting at $118 from Midway Intl. Airport (MDW) to Orlando Intl. Airport (MCO). 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 MDW on May 19 2025 and touching down at MCO. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from MDW to MCO?
The cheapest flights from MDW to MCO 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 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 MDW to MCO?
With tickets starting at $69 for a one-way journey from MDW to MCO, Frontier Airlines is currently the cheapest carrier for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on July 12 2025. Prices were last updated on April 24 2025 and have not changed since.
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.
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