RM385 Cheap Flights from Orlando (MCO) to Chicago (MDW)

View RM385 flight on Tue, 5 May 2026Opens 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 RM385 for one-way flights and RM1,408 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM1,408 Return, found 3 days ago
RM1,408
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM1,408 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM1,643 Return, found 3 days ago
RM1,643
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM1,643 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM1,878 Return, found 3 days ago
RM1,878
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM1,878 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM1,956 Return, found 3 days ago
RM1,956
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM1,956 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM2,191 Return, found 3 days ago
RM2,191
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM2,191 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM2,270 Return, found 3 days ago
RM2,270
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM2,270 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM2,505 Return, found 3 days ago
RM2,505
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM2,505 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM2,622 Return, found 3 days ago
RM2,622
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM2,622 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM2,858 Return, found 3 days ago
RM2,858
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM2,858 found 3 days ago
Delta
Fri, 1 May - Fri, 8 May
MCO
Orlando
MDW
Chicago
RM3,171 Return, found 3 days ago
RM3,171
Return
found 3 days ago
Select Delta flight, departing Fri, 1 May from Orlando to Chicago, returning Fri, 8 May, priced at RM3,171 found 3 days ago

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

February is typically the cheapest month to fly

From RM 264 - RM 1,150 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 RM1,408. 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.
Return price
RM1,408
Distance
1585 km
Average flight time
1 hour 55 mins

Book with confidence

Perfect flights from Orlando to Chicago

Your Journey from Orlando to Chicago

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Choosing Your Ideal Flight

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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 RM385 and roundtrip prices from RM1,408*.
 

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Book Your Flight from Orlando to Chicago with Confidence

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Orlando to Chicago

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