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Southwest Airlines flights from Orlando to Chicago

Southwest Airlines flies Orlando to Chicago nonstop 1 time a week, 2h 50m in the air. Tickets from $199 (the route's cheapest fare is $48).

Flights from Orlando to Chicago

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Prices by day: Orlando to Chicago

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

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Southwest Airlines on Orlando to Chicago at a glance

flights a week
1
days of operation
Sat
departure
07:05
flight time
2h 50m - 12h 55m
aircraft
Boeing 737, Boeing 737-800
departure terminal
A
cheapest fare, 26 November
$199
cheapest fare on the route
$48

Southwest Airlines Orlando to Chicago schedule

1 flight a week. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 2802
Southwest Airlines
07:05 Orlando International, terminal A
09:05 Chicago Midway International
3h
Sat
Boeing 737

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 26 November.

FlightDepartsArrivesDurationDaysAircraft
WN 2802
Southwest Airlines
07:10 Orlando International, terminal A
09:05 Chicago Midway International
2h 55m
Seasonal
Boeing 737
WN 2802
Southwest Airlines
07:00 Orlando International, terminal A
09:00 Chicago Midway International
3h
Seasonal
Boeing 737-800
WN 2543
Southwest Airlines
07:00 Orlando International, terminal A
08:55 Chicago Midway International
2h 55m
Seasonal
Boeing 737
WN 2543
Southwest Airlines
07:10 Orlando International, terminal A
09:05 Chicago Midway International
2h 55m
Seasonal
Boeing 737
WN 2532
Southwest Airlines
06:10 Orlando International, terminal A
18:05 Chicago Midway International
12h 55m
Seasonal
Boeing 737
WN 2543
Southwest Airlines
06:45 Orlando International, terminal A
08:40 Chicago Midway International
2h 55m
Seasonal
Boeing 737
WN 3378
Southwest Airlines
07:00 Orlando International, terminal A
10:25 Chicago Midway International
4h 25m
Seasonal
WN 4021
Southwest Airlines
07:10 Orlando International, terminal A
09:10 Chicago Midway International
3h
Seasonal
Boeing 737
WN 4021
Southwest Airlines
06:55 Orlando International, terminal A
08:55 Chicago Midway International
3h
Seasonal
Boeing 737
WN 4021
Southwest Airlines
07:00 Orlando International, terminal A
09:00 Chicago Midway International
3h
Seasonal
Boeing 737-800
WN 2718
Southwest Airlines
07:10 Orlando International, terminal A
09:05 Chicago Midway International
2h 55m
Seasonal
WN 1119
Southwest Airlines
06:10 Orlando International, terminal A
12:05 Chicago Midway International
6h 55m
Seasonal
WN 2718
Southwest Airlines
07:05 Orlando International, terminal A
09:00 Chicago Midway International
2h 55m
Seasonal
Boeing 737-800
WN 2505
Southwest Airlines
06:05 Orlando International, terminal A
07:55 Chicago Midway International
2h 50m
Seasonal
WN 2505
Southwest Airlines
06:50 Orlando International, terminal A
08:40 Chicago Midway International
2h 50m
Seasonal
WN 2505
Southwest Airlines
06:55 Orlando International, terminal A
08:45 Chicago Midway International
2h 50m
Seasonal
Boeing 737
WN 2505
Southwest Airlines
06:45 Orlando International, terminal A
08:35 Chicago Midway International
2h 50m
Seasonal
Boeing 737

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 1 hour behind Orlando.

Other airlines flying Orlando to Chicago

Nonstop flights by the current schedule

American Airlines United Airlines Frontier Airlines Allegiant Air All flights Orlando to Chicago

Frequently asked questions

How many Southwest Airlines flights are there from Orlando to Chicago?
1 nonstop flight a week, 8 flight numbers in the schedule: Sat.
How long is the Southwest Airlines flight from Orlando to Chicago?
From 2 hours 50 minutes to 12 hours 55 minutes nonstop, depending on the flight.
Which aircraft does Southwest Airlines fly from Orlando to Chicago?
Boeing 737 and Boeing 737-800.
Which terminals does Southwest Airlines use between Orlando and Chicago?
Southwest Airlines departs from Orlando International, terminal A and arrives at Chicago Midway International.
How much is a Southwest Airlines ticket from Orlando to Chicago?
The cheapest Southwest Airlines nonstop fare found recently is $199 for 26 November; the cheapest fare on the route with any airline is $48. The search shows the price for your date.