$34 Cheap Flights from Chicago to Orlando

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

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 $63 round trip and $34 one way. Prices and availability subject to change. Additional terms may apply.

Flight Schedule for MDW to MCO

CarrierFlightDepart MDWArrive MCOTue
F9102307:35 am11:11 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
0 Stops
F9102504:02 pm07:38 pmCheck FareCheck Fare
Check FareCheck Fare
0 Stops
F9102107:29 pm11:05 pm
Check Fare
Check Fare
0 Stops

Best Orlando Intl. Flight and Hotel Packages

Orlando Intl. flight + hotel packages - economy flights

Orbit One Vacation Villas
Eagle Trace Resort Orlando
ette hotel
Mi Casa Hotel
Alhambra Villas
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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 30 mins
Earliest Departure Time 5:30AM CST
Latest Departure Time 10:05PM CST
Lowest Flight Price $63

Route Info

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

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 $63 and $97. 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 $34. 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) 30 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, February 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.