CA $150 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 $150 for one-way flights and CA $288 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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Frequently asked questions

How much is a flight from Orlando Intl. Airport (MCO) to Midway Airport?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip flights between MCO and Midway Intl. Airport (MDW) start from CA $288. Book ASAP to secure the best price for your next big adventure. 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 Chicago Airport?
We understand that life can throw the odd curveball, so we’ve made it as easy as possible for you to cancel your trip online. Just head to the Customer Service Portal and follow the instructions.
How do I find cheap flights from Orlando Intl. Airport to Midway Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for Orlando Intl. Airport (MCO) to Midway Airport flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from Orlando Intl. Airport to Midway Airport?
Around 1,600 kilometers separates Orlando and Chicago, so pack something to keep you busy for a few hours. That juicy novel you haven’t had time to finish will be perfect.
Which airlines fly direct from Orlando Intl. Airport (MCO) to MDW?
Southwest Airlines (WN) is one of the top choices for travelers jetting between Orlando Intl. Airport (MCO) and Midway Airport. Select from the 217 flights it operates on this route each month. Operating 52 flights per month along this route, Frontier Airlines (F9) is another traveler favorite.
Are Orlando Intl. Airport to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Orlando Intl. Airport to Midway Intl. Airport (MDW) at the last minute could be your ticket to a great deal. However, it could end up costing a good deal more! If you’d rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains as far ahead as 12 months in advance. If your preferred carrier hasn’t released tickets yet, check back regularly as deals are updated on Expedia all the time.
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