RM673 Cheap Flights from Orlando (MCO) to Chicago (MDW)

View RM673 flight on Sat, 20 Sep 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 RM673 for one-way flights and RM2,178 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM2,178 Return, found 6 days ago
RM2,178
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM2,178 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM2,283 Return, found 6 days ago
RM2,283
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM2,283 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM2,516 Return, found 6 days ago
RM2,516
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM2,516 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM2,623 Return, found 6 days ago
RM2,623
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM2,623 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM2,856 Return, found 6 days ago
RM2,856
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM2,856 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM2,961 Return, found 6 days ago
RM2,961
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM2,961 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM3,479 Return, found 6 days ago
RM3,479
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM3,479 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM3,818 Return, found 6 days ago
RM3,818
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM3,818 found 6 days ago
Delta
Sat, 16 Aug - Sun, 17 Aug
MCO
Orlando
MDW
Chicago
RM4,158 Return, found 6 days ago
RM4,158
Return
found 6 days ago
Select Delta flight, departing Sat, 16 Aug from Orlando to Chicago, returning Sun, 17 Aug, priced at RM4,158 found 6 days ago

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

February is typically the cheapest month to fly

From RM 331 - RM 1,250 per traveller.

Graph displaying average flight prices per month

Orlando to Chicago route information
Origin airport
Orlando Intl.
Destination airport
Midway Intl.
Return price
RM2,178
Distance
1585 km
Average flight time
1 hour 45 mins

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 20 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 RM673 and roundtrip prices from RM2,178*.
 

Pre-Flight Essentials

Ensure a smooth journey from Orlando to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of Chicago. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Orlando to Chicago Flight

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.

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 RM2,178. 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.

Explore a world of travel with Expedia

*Available to Expedia members.