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

View $55 flight on Sun, Jul 27, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Orlando (MDW-MCO)

Prices were available within the past 7 days and start at $55 for one-way flights and $110 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, Sep 7 - Sat, Sep 13
MDW
Chicago
MCO
Orlando
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Sep 7 from Chicago to Orlando, returning Sat, Sep 13, priced at $110 just found
Frontier Airlines
Thu, Jul 17 - Sat, Jul 26
MDW
Chicago
MCO
Orlando
$119 Roundtrip, just found
$119
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jul 17 from Chicago to Orlando, returning Sat, Jul 26, priced at $119 just found
Frontier Airlines
Thu, Jul 10 - Wed, Jul 30
MDW
Chicago
MCO
Orlando
$126 Roundtrip, found 6 days ago
$126
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jul 10 from Chicago to Orlando, returning Wed, Jul 30, priced at $126 found 6 days ago
Frontier Airlines
Sat, Jul 19 - Mon, Jul 21
MDW
Chicago
MCO
Orlando
$128 Roundtrip, found 1 hour ago
$128
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Chicago to Orlando, returning Mon, Jul 21, priced at $128 found 1 hour ago
Frontier Airlines
Sat, Oct 4 - Sat, Oct 11
MDW
Chicago
MCO
Orlando
$130 Roundtrip, found 4 hours ago
$130
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Oct 4 from Chicago to Orlando, returning Sat, Oct 11, priced at $130 found 4 hours ago
Frontier Airlines
Mon, Jul 28 - Fri, Aug 1
MDW
Chicago
MCO
Orlando
$130 Roundtrip, just found
$130
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Jul 28 from Chicago to Orlando, returning Fri, Aug 1, priced at $130 just found
Frontier Airlines
Sat, Jul 12 - Mon, Aug 25
MDW
Chicago
MCO
Orlando
$134 Roundtrip, found 5 hours ago
$134
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Chicago to Orlando, returning Mon, Aug 25, priced at $134 found 5 hours ago
Southwest Airlines
Mon, Aug 11 - Thu, Aug 14
MDW
Chicago
MCO
Orlando
$136 Roundtrip, just found
$136
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Aug 11 from Chicago to Orlando, returning Thu, Aug 14, priced at $136 just found
Frontier Airlines
Tue, Aug 12 - Sat, Aug 16
MDW
Chicago
MCO
Orlando
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Aug 12 from Chicago to Orlando, returning Sat, Aug 16, priced at $138 just found
Delta
Wed, Sep 10 - Sat, Sep 13
MDW
Chicago
MCO
Orlando
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Delta flight, departing Wed, Sep 10 from Chicago to Orlando, returning Sat, Sep 13, priced at $154 just found

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

February is typically the cheapest month to fly

From $84 - $568 per traveler.

Graph displaying average flight prices per month

Alternative airports near Orlando

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Orlando Intl. MCO. Cheapest option available. Average driving time to city center is 19 minutes. Flights from $119
MCO
Orlando Intl.
Cheapest
Average driving time to city center19 min
Flights from $119
Flights from Chicago (MDW) to Orlando (MCO)
Origin airport
Midway Intl.
Destination airport
Orlando Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$104
Distance
991 mi
Average flight time
3 hours 39 mins

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 September. 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 $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 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.

 

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 $104 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 July 26 2025 and touching down at MCO. The price was last updated on July 2 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 $55 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 September 19 2025. Prices were last updated on July 2 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.

Explore a world of travel with Expedia

*Available to One Key members.