Airlines with flights from Chicago to Orlando
There are three airlines with scheduled flights between MDW and MCO. Southwest is the only airline with non-stop flights from Midway International Airport to Orlando International and the flight time is 2 hours and 35 minutes.
There are three airlines with scheduled flights between MDW and MCO. Southwest is the only airline with non-stop flights from Midway International Airport to Orlando International and the flight time is 2 hours and 35 minutes. Choose airline
Direct
Non-stop
2h 35min
Via Nashville
3h 55min
Via Atlanta
3h 55min
Via Indianapolis
4h 0min
Via Louisville
4h 0min
Via Columbus
4h 5min
Via Atlanta
4h 9min
Via Saint Louis
4h 10min
Via Raleigh/Durham
4h 15min
Via Cleveland
4h 15min
Via Milwaukee
4h 15min
Via Pittsburgh
4h 20min
Via Detroit
4h 23min
Via Fort Myers
4h 30min
Via Sarasota
4h 30min
Via Fort Lauderdale
4h 35min
Via New Orleans
4h 40min
Via Kansas City
4h 45min
Via Atlanta
4h 46min
Via Baltimore
4h 50min
Via Washington
4h 55min
Via Birmingham
5h 0min
Via Cincinnati
5h 15min
Via Minneapolis
5h 24min
Via Philadelphia
5h 25min
Via Buffalo
5h 30min
Via Rochester
5h 35min
Via Omaha
6h 15min
Starts 06/06
Via Norfolk
4h 55min
Starts 06/06
Via Memphis
6h 25min
Starts 06/06
Via Minneapolis
6h 40min
Starts 07/06
Via Tulsa
6h 45min
NEW
Starts 04/07
Via Richmond
5h 40min
Starts 08/08
Via Miami
5h 30min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 35 minutes
-
Low-cost airline
-
Chicago and Orlando are both Southwest Airlines focus cities.
-
70 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
MCO
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2815
05:10
05:10
05:10
05:10
05:10
----
----
WN2816
06:30
----
----
06:30
06:30
07:45
07:50
WN3535
----
07:55
07:55
----
----
----
----
WN2817
08:00
16:40
16:40
08:00
08:00
----
----
WN1355
----
----
----
----
----
08:55
----
WN2732
----
09:00
09:00
----
----
----
----
WN1102
----
----
----
----
----
----
09:05
WN5061
09:40
----
----
09:40
09:40
----
----
WN2818
11:00
12:00
12:00
11:00
11:00
10:05
16:55
WN114
----
----
----
----
----
----
11:15
WN644
----
----
----
----
----
12:50
----
WN2819
13:40
14:40
14:40
13:40
13:40
----
----
WN2820
18:35
----
----
18:35
18:35
15:50
----
WN251
----
----
----
----
----
17:05
----
WN164
17:10
----
----
17:10
17:10
----
----
WN3123
----
17:30
17:30
----
----
----
----
WN1603
----
----
----
----
----
----
18:40
WN2821
20:55
20:10
20:10
20:55
20:55
19:35
20:35
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 3h 55m - 8h 05m.
-
Low-cost airline
-
Chicago and Orlando are both Southwest Airlines focus cities.
-
157 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via BNA
MCO
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3855
WN568
WN568
----
----
----
----
----
----
06:10
WN1053
WN569
WN569
----
----
----
----
----
06:40
----
WN2959
WN4206
WN4206
07:15
----
----
07:15
07:15
----
----
WN1337
WN4206
WN4206
----
----
----
----
----
----
07:55
WN1775
WN4714
WN4714
07:55
----
----
07:55
07:55
----
----
WN2959
WN3338
WN3338
----
08:40
08:40
----
----
----
----
WN1257
WN4714
WN4714
09:00
----
----
09:00
09:00
----
----
WN2732
WN1035
WN1035
----
----
----
----
----
09:15
----
WN2733
WN569
WN569
11:20
11:50
11:50
11:20
11:20
----
----
WN533
WN569
WN569
----
----
----
----
----
----
11:50
WN3869
WN571
WN571
----
15:10
15:10
----
----
----
----
WN1257
WN571
WN571
----
----
----
----
----
15:30
----
WN3614
WN571
WN571
----
----
----
----
----
----
16:40
WN3869
WN572
WN572
17:05
----
----
17:05
17:05
----
----
WN1073
WN572
WN572
----
17:20
17:20
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Southwest Airlines
-
Total flight time: 3h 55m - 6h 15m.
-
Low-cost airline
-
Chicago and Orlando are both Southwest Airlines focus cities.
-
60 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via ATL
MCO
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3054
WN215
WN215
07:15
07:45
07:45
07:15
07:15
----
----
WN1306
WN4433
WN4433
----
13:00
13:00
----
----
----
----
WN4592
WN4558
WN4558
14:40
----
----
14:40
14:40
13:15
----
The timetable & schedule information was updated at 2026-04-21
Via Indianapolis with Southwest Airlines
-
Total flight time: 4h 00m - 7h 45m.
-
Low-cost airline
-
Chicago and Orlando are both Southwest Airlines focus cities.
-
23 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via IND
MCO
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3877
WN4537
WN4537
----
10:10
10:10
----
----
----
----
WN3271
WN4722
WN4722
----
----
----
----
----
10:20
----
The timetable & schedule information was updated at 2026-04-21
Via Louisville with Southwest Airlines
-
Total flight time: 4h 00m - 6h 15m.
-
Low-cost airline
-
Chicago and Orlando are both Southwest Airlines focus cities.
-
18 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via SDF
MCO
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN670
WN1910
WN1910
----
----
----
----
----
11:30
----
WN4473
WN910
WN910
12:45
----
----
12:45
12:45
----
----
WN3743
WN1184
WN1184
----
13:25
13:25
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta
Via Atlanta with Frontier