RM1,348 Cheap Flights from Orlando (MCO) to Chicago (MDW)

View RM1,348 flight on Fri, 17 Oct 2025Opens in a new window

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

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Cheap Flights from Orlando to Chicago (MCO-MDW)

Prices were available within the past 7 days and start at RM1,348 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

February is typically the cheapest month to fly

From RM 336 - RM 1,510 per traveller.

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 . 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 kilometres 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 travellers 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 traveller favourite.
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.

Travel information

Origin airport
Orlando Intl.
Destination airport
Midway Intl.
Distance
1585 km
Average flight time
1 hour 45 mins

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Perfect flights from Orlando to Chicago

Your Journey from Orlando to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Orlando to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Orlando Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 1 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Orlando to Chicago Flights

Experience the joy of finding cheap flights from Orlando Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from RM1,348 and roundtrip prices *.
 

Pre-Flight Essentials

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Experience the Vibrant Chicago

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Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Orlando to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Orlando to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Orlando to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Orlando to Chicago

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