Flights from Orlando to Chicago Midway

Flights a week: <1
Flight time: 2 h 50 min
Distance: 1,595 km

Schedule, today's status and punctuality of flights from Orlando to Chicago Midway, from the official airport boards. Times are local to each airport.

Flights on 4 October 2026

Flight	Departure	Arrival	Status
WN2742Southwest Airlines	06:45	08:35	Departed
WN534Southwest Airlines	~~10:10~~ 10:23	~~12:00~~ 12:06	Departed
WN2771Southwest Airlines	~~11:55~~ 12:05	13:45	Departed
WN979Southwest Airlines	~~15:30~~ 16:15	~~17:25~~ 17:46	Departed
WN2746Southwest Airlines	~~17:20~~ 17:35	~~19:10~~ 19:18	Departed
WN3651Southwest Airlines	~~18:55~~ 19:39	~~20:45~~ 20:55	Boarding
WN693Southwest Airlines	22:20	—	Scheduled

Local times: departure in the departure airport's time, arrival in the arrival airport's. Struck through: the scheduled time.

Flight numbers from Orlando to Chicago Midway

From the last 28 days of boards: usual departure time, the weekdays it flew and the share of on-time departures (within 15 min).

WN274206:45
WN215208:10
WN53410:10
WN156810:40
WN277111:55
WN249014:25
WN97915:30
WN274617:20
WN167018:30
WN365118:55
WN69322:20

Common questions

Which airlines fly from Orlando to Chicago Midway?: Southwest Airlines.
How many flights a week are there from Orlando to Chicago Midway?: About <1 a week over the last 28 days of boards. Flight numbers on the route: 11.
How long is the flight from Orlando to Chicago Midway?: About 2 h 50 min by the schedule. The airports are 1595 km apart.

Airports

Departure: Orlando (MCO)
Arrival: Chicago Midway (MDW)
Return flights from Chicago Midway to Orlando <1 a week