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

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

Popular airlines from Chicago Midway Airport (MDW) to Orlando Executive Airport (ORL)

Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Orlando (MDW-ORL)

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, May 31 - Sat, Jun 7
MDW
Chicago
MCO
Orlando
$120 Roundtrip, found 2 hours ago
$120
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Chicago to Orlando, returning Sat, Jun 7, priced at $120 found 2 hours ago
Frontier Airlines
Sat, Jul 26 - Sat, Aug 2
MDW
Chicago
MCO
Orlando
$128 Roundtrip, found 2 hours ago
$128
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Jul 26 from Chicago to Orlando, returning Sat, Aug 2, priced at $128 found 2 hours ago
Frontier Airlines
Sun, Jun 1 - Sat, Jun 7
MDW
Chicago
MCO
Orlando
$129 Roundtrip, just found
$129
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Jun 1 from Chicago to Orlando, returning Sat, Jun 7, priced at $129 just found
Frontier Airlines
Sat, Jun 14 - Thu, Jun 19
MDW
Chicago
MCO
Orlando
$130 Roundtrip, just found
$130
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jun 14 from Chicago to Orlando, returning Thu, Jun 19, priced at $130 just found
Frontier Airlines
Sat, Jun 28 - Thu, Jul 3
MDW
Chicago
MCO
Orlando
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jun 28 from Chicago to Orlando, returning Thu, Jul 3, priced at $133 found 1 hour ago
Frontier Airlines
Fri, Jul 18 - Sat, Jul 26
MDW
Chicago
MCO
Orlando
$134 Roundtrip, just found
$134
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 18 from Chicago to Orlando, returning Sat, Jul 26, priced at $134 just found
Frontier Airlines
Thu, May 22 - Mon, Jun 9
MDW
Chicago
MCO
Orlando
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, May 22 from Chicago to Orlando, returning Mon, Jun 9, priced at $138 just found
Frontier Airlines
Sun, Jun 15 - Thu, Jun 19
MDW
Chicago
MCO
Orlando
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Jun 15 from Chicago to Orlando, returning Thu, Jun 19, priced at $139 found 1 hour 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
Delta
Wed, May 28 - Sat, Jun 7
MDW
Chicago
MCO
Orlando
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, May 28 from Chicago to Orlando, returning Sat, Jun 7, priced at $169 found 1 hour ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) cost?
Discover the latest flight deals from MDW to ORL by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to ORL?
The cheapest flights from MDW to ORL are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to ORL?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to ORL. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
Direct flights from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) aren’t available daily, so you’ll need to take a flight with a layover. Explore your options with Expedia’s filters. Enter your travel dates and click on either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from MDW to ORL?
Generally you’ll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* However, this can change based on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
Choose a flight from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL) that leaves before 3 PM to reduce the likelihood of delays. Departures later than this are on average 22% more likely to be canceled.**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 Executive Airport (ORL) last-minute?
Last-minute fares from MDW to ORL are typically more expensive. To secure the lowest rates, start looking for flights well ahead of time. That being said, if you can play around with your travel dates, it’s possible to land a cheap ticket right before your trip.
Is it cheaper to book a MDW to ORL flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to ORL flight and hotel package with Expedia could result in significant savings. What’s more, having everything in one convenient place will take the stress out of travel planning. Just secure your flights and choose from our extensive range of stays, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Orlando Executive Airport (ORL)?
In most instances, you can modify or cancel your MDW to ORL flight. However, there may be additional fees, especially if your booking was made more than 24 hours ago. Double-check your itinerary for the airline’s fees and policies on flight changes, or if you want further details, visit our Customer Service portal.
*Available to One Key members.