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
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).
-
41 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
DCA
Direct
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1409
----
06:05
06:05
07:25
07:25
06:10
07:55
WN1442
07:30
----
----
----
----
----
----
WN814
----
----
----
09:10
09:10
----
----
WN1444
09:25
----
----
----
----
----
----
WN122
----
----
----
----
----
----
09:30
WN2252
----
09:35
09:35
15:35
15:35
10:40
15:35
WN1445
12:00
----
----
----
----
----
----
WN4129
----
13:00
13:00
----
----
----
----
WN124
----
----
----
13:00
13:00
----
----
WN110
----
----
----
----
----
13:00
----
WN1523
----
----
----
----
----
----
13:00
WN4479
15:35
----
----
----
----
----
----
WN1411
----
16:35
16:35
----
----
15:40
----
WN1413
----
18:40
18:40
18:40
18:40
18:40
18:00
WN1447
19:05
----
----
----
----
----
----
WN1448
21:00
----
----
----
----
----
----
WN2679
----
21:00
21:00
----
----
----
21:30
WN3196
----
----
----
21:15
21:15
----
----
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 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
DCA
Via CMH
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2658
WN1182
WN1182
----
11:40
11:40
----
----
13:20
----
WN3588
WN1350
WN1350
----
----
----
----
----
----
11:45
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
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL2869
DL4684
DL4684
06:00
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 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
DCA
Via STL
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN391
WN3862
WN3862
----
08:00
08:00
----
----
----
----
WN2431
WN3861
WN3861
----
----
----
08:15
08:15
----
----
WN2031
WN2742
WN2742
----
----
----
----
----
----
12:00
WN1678
WN3864
WN3864
----
12:00
12:00
----
----
----
----
WN4752
WN556
WN556
12:00
----
----
----
----
----
----
WN2442
WN3862
WN3862
----
----
----
12:15
12:15
----
----
WN1678
WN2052
WN2052
----
----
----
----
----
12:30
----
WN1461
WN2289
WN2289
14:35
----
----
----
----
----
----
WN3362
WN3001
WN3001
----
----
----
15:30
15:30
----
----
WN1949
WN2032
WN2032
----
----
----
----
----
----
15:40
WN1462
WN3957
WN3957
18:40
----
----
----
----
----
----
WN1726
WN3865
WN3865
----
----
----
18:50
18:50
----
----
WN4166
WN3865
WN3865
----
18:50
18:50
----
----
----
----
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 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)
DCA
Via BNA
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1388
WN4895
WN4895
----
06:05
06:05
----
----
----
----
WN1425
WN507
WN507
06:35
----
----
----
----
----
----
WN955
WN573
WN573
----
----
----
06:55
06:55
----
----
WN1389
WN684
WN684
----
----
----
----
----
----
09:10
WN668
WN311
WN311
----
----
----
----
----
10:05
----
WN1390
WN577
WN577
----
----
----
10:40
10:40
----
----
WN1566
WN575
WN575
----
----
----
----
----
----
12:40
WN1427
WN2241
WN2241
13:00
----
----
----
----
----
----
WN1503
WN575
WN575
----
13:00
13:00
----
----
----
----
WN1388
WN575
WN575
----
----
----
13:30
13:30
----
----
WN368
WN4549
WN4549
----
----
----
----
----
14:30
----
WN1390
WN576
WN576
----
15:50
15:50
----
----
----
----
WN4301
WN4549
WN4549
----
----
----
----
----
15:55
----
WN1566
WN576
WN576
----
----
----
16:30
16:30
----
----
WN1428
WN578
WN578
19:00
----
----
----
----
----
----
WN2843
WN577
WN577
----
19:00
19:00
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
