Direct flights from Orlando to Chicago
All flights from MCO to MDW non-stop. There are direct flights from Orlando International (MCO), Florida, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines and Frontier Airlines. 56 weekly departures are currently scheduled on this route. Departure times range from 06:20 to 22:55 depending on the schedule period. The flight distance is 996 miles (1603 km). Flight time ranges from 2 hours and 40 minutes to 3 hours and 1 minutes.
Orlando
, USA
Flight schedule from Orlando to Chicago with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-07-13
Flight schedule from Orlando to Chicago with Frontier Airlines
This is a weekly direct flight schedule for Frontier Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at
Orlando to Chicago scheduled departures
Select a date to see every published non-stop departure between MCO and MDW.
MCO - MDW route facts
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Distance996 miles (1603 km)
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Flight time2 hours and 40 minutes to 3 hours and 1 minutes
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Airlines Southwest
Frontier -
Airline alliancesLow-cost carrier
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CabinsEconomy
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AircraftSouthwest Airlines: Boeing 737MAX 8 Passenger, Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737-700 Passenger (Scimitar Winglets)Frontier Airlines: Airbus A320neo and Airbus A321neo
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