$59 Cheap flights from Midway Intl. to Orlando Intl. (MDW to MCO)

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Find The Best Dates To Fly from Midway Intl. to Orlando Intl.

Amazing MDW to MCO Flight Deals

The cheapest flights to Orlando Intl. found within the past 7 days were $118 round trip and $59 one way. Prices and availability subject to change. Additional terms may apply.

Mon, Dec 16 - Wed, Dec 18
MDW
Chicago
MCO
Orlando
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Dec 16 from Chicago to Orlando, returning Wed, Dec 18, priced at $118 just found
Thu, Nov 21 - Mon, Nov 25
MDW
Chicago
MCO
Orlando
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Nov 21 from Chicago to Orlando, returning Mon, Nov 25, priced at $120 found 2 days ago
Mon, Dec 16 - Wed, Dec 18
MDW
Chicago
MCO
Orlando
$122 Roundtrip, just found
$122
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Dec 16 from Chicago to Orlando, returning Wed, Dec 18, priced at $122 just found
Mon, Feb 24 - Wed, Feb 26
MDW
Chicago
MCO
Orlando
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Feb 24 from Chicago to Orlando, returning Wed, Feb 26, priced at $123 found 1 day ago
Mon, Dec 16 - Wed, Dec 18
MDW
Chicago
MCO
Orlando
$126 Roundtrip, just found
$126
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Dec 16 from Chicago to Orlando, returning Wed, Dec 18, priced at $126 just found
Mon, Dec 16 - Thu, Dec 19
MDW
Chicago
MCO
Orlando
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 16 from Chicago to Orlando, returning Thu, Dec 19, priced at $127 found 1 day ago
Fri, Jan 10 - Thu, Jan 16
MDW
Chicago
MCO
Orlando
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jan 10 from Chicago to Orlando, returning Thu, Jan 16, priced at $128 found 2 days ago
Fri, Nov 22 - Sat, Nov 23
MDW
Chicago
MCO
Orlando
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Nov 22 from Chicago to Orlando, returning Sat, Nov 23, priced at $131 found 3 days ago
Fri, Dec 13 - Tue, Dec 17
MDW
Chicago
MCO
Orlando
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Dec 13 from Chicago to Orlando, returning Tue, Dec 17, priced at $132 found 2 hours ago
Wed, Dec 18 - Fri, Dec 20
MDW
Chicago
MCO
Orlando
$134 Roundtrip, found 1 hour ago
$134
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Dec 18 from Chicago to Orlando, returning Fri, Dec 20, priced at $134 found 1 hour ago

Best Orlando Intl. Flight and Hotel Packages

Orlando Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Orlando (MCO)
The Kenwood Inn

The Kenwood Inn

3.5 out of 5
Save 100% on your flight
per person
Jan 8 - Jan 15
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 30
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
per person
Jan 11 - Jan 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Orlando (MCO)
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Frequently asked questions

Can I catch a flight from Chicago Airport to Orlando Intl. Airport right now?
Make sure you check out our Covid-19 Travel Advisor to learn if there are any present travel advice reports or quarantine requirements in effect in MCO when flying from Midway Airport.
Are there direct flights from Midway Intl. Airport (MDW) to Orlando Intl. Airport?
The only thing separating you and your next memorable adventure is just one flight. Southwest Airlines is the only air carrier that offers direct services between Midway Intl. Airport (MDW) and MCO, so it’s smart to book well in advance.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Orlando Intl. Airport (MCO), please visit our Customer Service Portal.
How long is the flight from MDW to Orlando Intl. Airport (MCO)?
On average, traveling from Midway Airport to Orlando Intl. Airport takes a quick 2 hours and 34 minutes in total. Use the short trip to rest your eyelids for a while or listen to a podcast before the next part of your adventure begins.
What is the flight distance from Chicago Airport to Orlando Intl. Airport?
Covering 990 mi between Chicago Airport and Chicago Airport calls for a glass of red and some screen time. Adjust your seat, pull a blanket over your lap and enjoy the ride.
What airlines fly from Midway Intl. Airport (MDW) to Orlando Intl. Airport?
With Southwest Airlines, you won’t have to put up with extended layovers or sitting around waiting to catch your next flight. This popular airline company will take you directly from Chicago Airport to Orlando Intl. Airport (MCO) on one of the 225 flights offered on this route every month.
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with Southwest Airlines, Spirit Airlines or Frontier Airlines you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

 

Traveling From
Midway Intl.
Traveling To
Orlando Intl.
Shortest Flight Time
2 hours 35 mins
Earliest Departure Time
5:10AM CST
Latest Departure Time
8:00PM CST
Lowest Flight Price
$118

Route Info

Flight path for flights from Chicago Midway International Airport to Orlando International Airport.


Origin:
MDW - Chicago Midway International Airport
Destination:
MCO - Orlando International Airport
Distance:
996.00 miles


Discover our best flights from Chicago MDW to Orlando MCO. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Chicago MDW to Orlando MCO at the right price  

Airfares to Orlando MCO from Chicago MDW currently cost between $118 and $134. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Chicago MDW to Orlando MCO 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Chicago MDW to Orlando MCO on Travelocity starting at $59. Prices and availability subject to change. Additional terms may apply. 

 

Get to Orlando MCO from Chicago MDW quicker with direct flights. 

Get to Orlando faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MCO from MDW to take around 2 hour(s) 35 min(s).  

 

Find our cheapest airfares for flights from Chicago MDW to Orlando MCO

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MCO from MDW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Chicago MDW to Orlando MCO today 

If you’re flexible about when you travel, December is usually the cheapest month to fly from Chicago MDW to Orlando MCO. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Orlando MCO from Chicago MDW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MCO from MDW have this option.  

 

Travel with confidence when you book flights to Orlando MCO from Chicago MDW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.