Skip to main content
Beginning of main content

Cheap Flights from Orlando to Chicago $178.25

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia’s Price Guarantee
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheapest Flights from Orlando to Chicago (MCO to MDW)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Orlando to Chicago (MCO to MDW)

Question : Which airline has been on time from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) the most?
Answer : Southwest Airlines will have you to MDW on schedule 88% of the time. Life has too much to offer to spend it waiting in an airport, so check out Southwest Airlines to get in and out of airports as quickly as possible. Note that if they do have a delay, it usually lasts about 10-20 minutes.

Question : Over the coming months, which airline is getting its passengers to Chicago Midway International Airport (MDW) round-trip the cheapest?
Answer : Check out Delta Air Lines, as they have been booking customers at lower fares than most.

Question : Should you be aware of any airlines that have a reputation of delays for this route?
Answer : Executive Jet Management flights from MCO to MDW are late 100% of the time. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : How long do most people stay in Chicago when they fly in from Orlando?
Answer : Of course you're not most people, but if you were, you'd stay roughly four days.

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : Since low prices are preferred, look at January 26th. As of January 16th, the cheapest ticket sales are coming in 29% below the average price for this route, so you can spend that extra cash on an adventure rather than the flight.