Airlines with flights from Miami to Chicago
There are three airlines with scheduled flights between MIA and MDW. Southwest is the only airline with non-stop flights from Miami International to Midway International Airport and the flight time is 3 hours and 10 minutes.
There are three airlines with scheduled flights between MIA and MDW. Southwest is the only airline with non-stop flights from Miami International to Midway International Airport and the flight time is 3 hours and 10 minutes. Choose airline
Direct
Non-stop
3h 10min
Via Saint Louis
4h 25min
Via Orlando
4h 35min
Via Nashville
4h 40min
Via Columbus
4h 40min
Via Atlanta
4h 44min
Via Baltimore
5h 10min
Via Kansas City
5h 15min
Via Detroit
5h 24min
Via Atlanta
5h 40min
Starts 06/06
Via Pittsburgh
5h 40min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 3 hours and 10 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
9 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
MIA
Direct
MDW
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
WN2930
14:50
16:00
16:00
14:50
14:50
15:35
15:15
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 4h 25m - 9h 15m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
23 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
MIA
Via STL
MDW
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
WN2931
WN2570
WN2570
05:40
----
----
05:40
05:40
----
05:50
WN2931
WN1373
WN1373
----
07:40
07:40
----
----
----
----
WN3188
WN3957
WN3957
----
----
----
----
----
18:05
----
WN2888
WN3957
WN3957
----
----
----
----
----
----
19:10
The timetable & schedule information was updated at 2026-04-21
Via Orlando with Southwest Airlines
-
Total flight time: 4h 35m - 8h 40m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
53 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
MIA
Via MCO
MDW
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
WN1698
WN2667
WN2667
----
----
----
----
----
----
05:35
WN4086
WN2654
WN2654
05:35
----
----
05:35
05:35
----
----
WN2715
WN2835
WN2835
----
06:00
06:00
----
----
----
----
WN3168
WN2835
WN2835
----
----
----
----
----
06:20
----
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 4h 40m - 8h 00m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
71 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
MIA
Via BNA
MDW
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
WN2922
WN1009
WN1009
----
----
----
----
----
----
10:05
WN2825
WN2241
WN2241
----
11:25
11:25
----
----
----
----
WN2922
WN1430
WN1430
----
----
----
----
----
13:05
----
WN4799
WN4286
WN4286
16:00
16:20
16:20
16:00
16:00
----
----
WN4799
WN578
WN578
----
----
----
----
----
19:25
----
WN1689
WN578
WN578
----
----
----
----
----
----
20:20
The timetable & schedule information was updated at 2026-04-21
Via Columbus with Southwest Airlines
-
Total flight time: 4h 40m - 6h 10m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
11 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
MIA
Via CMH
MDW
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
WN2925
WN1199
WN1199
12:50
----
----
12:50
12:50
----
----
WN2925
WN1200
WN1200
----
----
----
----
----
----
15:10
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta
Via Atlanta with Frontier