Airlines with flights from Washington to Chicago
There are two airlines with scheduled flights between DCA and MDW. Southwest is the only airline with non-stop flights from Reagan National to Midway International Airport and the flight time is 2 hours and 5 minutes.
There are two airlines with scheduled flights between DCA and MDW. Southwest is the only airline with non-stop flights from Reagan National to Midway International Airport and the flight time is 2 hours and 5 minutes. Choose airline
Direct
Non-stop
2h 5min
Via Columbus
3h 20min
Via Detroit
3h 30min
Via Saint Louis
4h 0min
Via Nashville
4h 15min
NEW
Starts 06/06
Via Milwaukee
5h 15min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 5 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
54 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
DCA
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
WN1442
07:30
06:00
06:00
07:30
07:30
----
07:55
WN2859
----
----
----
----
----
06:10
----
WN1444
09:25
09:30
09:30
09:25
09:25
----
----
WN1431
----
----
----
----
----
----
09:25
WN554
----
----
----
----
----
10:40
----
WN488
----
----
----
----
----
----
12:00
WN1445
12:00
12:00
12:00
12:00
12:00
----
----
WN277
----
----
----
----
----
13:10
----
WN4479
15:35
16:25
16:25
15:35
15:35
16:30
15:10
WN2904
----
----
----
----
----
18:40
----
WN1447
18:55
----
----
18:55
18:55
----
----
WN2710
----
18:55
18:55
----
----
----
----
WN2852
----
----
----
----
----
----
20:00
WN1448
21:00
21:30
21:30
21:00
21:00
----
----
WN370
----
----
----
----
----
----
21:35
The timetable & schedule information was updated at 2026-04-21
Via Columbus with Southwest Airlines
-
Total flight time: 3h 20m - 5h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
25 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
DCA
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
WN1429
WN1199
WN1199
----
11:40
11:40
----
----
----
----
WN1426
WN66
WN66
----
----
----
----
----
15:50
----
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
-
Total flight time: 3h 30m - 4h 14m.
-
Sky Team Alliance
-
58 flights per week
DCA
Via DTW
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
DL5839
DL4684
DL4684
----
----
----
----
----
06:00
----
DL2869
DL4684
DL4684
06:00
06:00
06:00
06:00
06:00
----
06:00
DL1558
DL4688
DL4688
09:39
09:39
09:39
09:39
09:39
09:39
09:39
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 4h 00m - 8h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
96 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
DCA
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
WN4853
WN1373
WN1373
----
08:00
08:00
----
----
----
----
WN225
WN556
WN556
----
11:45
11:45
----
----
----
----
WN4752
WN556
WN556
12:00
----
----
12:00
12:00
----
----
WN644
WN556
WN556
----
12:00
12:00
----
----
----
----
WN4752
WN2468
WN2468
----
----
----
----
----
12:40
----
WN1461
WN2289
WN2289
14:35
15:00
15:00
14:35
14:35
----
----
WN2535
WN556
WN556
----
----
----
----
----
----
14:40
WN1462
WN3957
WN3957
18:40
18:40
18:40
18:40
18:40
18:35
----
WN2712
WN3957
WN3957
----
----
----
----
----
----
18:40
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 4h 15m - 8h 00m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
147 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
DCA
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
WN1425
WN1473
WN1473
----
06:10
06:10
----
----
----
----
WN1425
WN507
WN507
06:35
----
----
06:35
06:35
----
----
WN1426
WN1009
WN1009
----
----
----
----
----
----
09:15
WN1426
WN1430
WN1430
----
10:35
10:35
----
----
----
----
WN2077
WN478
WN478
----
----
----
----
----
----
13:00
WN1900
WN2241
WN2241
----
13:00
13:00
----
----
----
----
WN1427
WN2241
WN2241
13:00
----
----
13:00
13:00
----
----
WN1427
WN4286
WN4286
----
16:00
16:00
----
----
----
----
WN1770
WN4277
WN4277
----
----
----
----
----
----
17:35
WN1428
WN578
WN578
19:00
19:55
19:55
19:00
19:00
----
19:55
The timetable & schedule information was updated at 2026-04-21
