CA $136 Cheap Flights from Orlando (MCO) to Chicago (MDW)

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

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Cheap flights from Orlando (MCO) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $136 for one-way flights and CA $810 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta

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

February is typically the cheapest month to fly

From CA $108 - CA $511 per traveller.

Graph displaying average flight prices per month

Flight from Orlando to Chicago (MCO - MDW) route information
Origin airport
Orlando Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
CA $810
Distance
1585 km
Average flight time
1 hour 43 mins

Orlando to Chicago Flights

The easy way to book your flights from Orlando to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Orlando whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are Frontier Airlines, Southwest Airlines nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Orlando to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Orlando Intl., MCO to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Orlando to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Orlando currently is just CA $810 rising to CA $963.  

Here are more money-saving tips: 

  • Fly in August when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Orlando 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Frequently asked questions

How much is a flight from Orlando Intl. Airport to Midway Intl. Airport (MDW)?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from MCO to Chicago Airport was CA $810. Cheap tickets don't hang around forever, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Orlando Intl. Airport (MCO) to Midway Airport?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from Orlando Intl. Airport to Midway Intl. Airport (MDW) that have flexible change policies?
Use our "No change fees" filter to find flexible ticketing options for your flight from Orlando Intl. Airport (MCO) to Chicago Airport. This allows you to snag a great price ahead of time and still have the freedom to reschedule without any extra fees. Fare adjustments may apply if your new flight is more expensive.
How many hours is the flight from Orlando Intl. Airport (MCO) to Chicago Airport?
Sit back, choose a movie and 2 hours and 56 minutes will whiz by in the blink of an eye. That's how long it takes to travel to MDW from MCO.
How far is the flight from MCO to Midway Airport?
Around 1,600 kilometres separates Orlando and Chicago, so pack some in-flight entertainment to help you fill in a couple of hours. That gripping novel you've yet to start will be just the ticket.
Which airlines fly direct from Orlando Intl. Airport to Midway Airport?
There are several airlines that travel directly from MCO to Midway Airport. Southwest Airlines (WN) is a popular option, offering 182 flights on this route each month. You could also check out the fares available with Frontier Airlines (F9). This carrier operates 13 flights every month between Orlando and Chicago.
Are MCO to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Flight tickets from Orlando Intl. Airport (MCO) to MDW are available up to 12 months before departure on Expedia. And although you may pick up a great last-minute deal, it's never a sure thing. Also, booking your flights ahead of time means you'll have more choices — and you can avoid getting trapped in the dreaded middle seat! We're always updating our fares to bring you the biggest bargains, so check back often for all the latest specials.

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