Airlines with flights from Chicago to Hartford
There are two airlines with scheduled flights between MDW and BDL. Southwest is the only airline with non-stop flights from Midway International Airport to Bradley International and the flight time is 2 hours and 5 minutes.
There are two airlines with scheduled flights between MDW and BDL. Southwest is the only airline with non-stop flights from Midway International Airport to Bradley International and the flight time is 2 hours and 5 minutes. Choose airline
Direct
Non-stop
2h 5min
Via Detroit
3h 34min
Via Baltimore
3h 40min
Via Nashville
4h 30min
NEW
Starts 04/08
Via Cleveland
5h 15min
Starts 06/08
Via Saint Louis
6h 10min
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).
-
25 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Direct
BDL
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
WN2731
07:45
07:50
07:50
07:45
07:45
----
07:40
WN174
----
----
----
----
----
07:45
----
WN692
13:30
12:50
12:50
13:30
13:30
----
----
WN970
----
----
----
----
----
17:45
----
WN1593
----
18:45
18:45
----
----
----
----
WN1451
----
----
----
----
----
----
18:50
WN1603
19:50
----
----
19:50
19:50
----
----
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
-
Total flight time: 3h 34m - 5h 58m.
-
Sky Team Alliance
-
63 flights per week
MDW
Via DTW
BDL
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
DL4674
DL2814
DL2814
09:17
09:17
09:17
09:17
09:17
09:17
09:17
DL4690
DL2989
DL2989
18:58
18:58
18:58
18:58
18:58
18:35
18:58
The timetable & schedule information was updated at 2026-04-21
Via Baltimore with Southwest Airlines
-
Total flight time: 3h 40m - 8h 25m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
140 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via BWI
BDL
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
WN2742
WN427
WN427
07:00
----
----
07:00
07:00
05:15
----
WN1120
WN427
WN427
----
06:00
06:00
----
----
----
----
WN1306
WN427
WN427
----
----
----
----
----
----
07:10
WN748
WN1143
WN1143
----
----
----
----
----
----
07:45
WN758
WN1833
WN1833
----
----
----
----
----
07:45
----
WN937
WN477
WN477
----
07:50
07:50
----
----
----
----
WN1355
WN477
WN477
----
08:10
08:10
----
----
----
----
WN1355
WN1143
WN1143
08:55
----
----
08:55
08:55
----
----
WN3877
WN428
WN428
----
10:10
10:10
----
----
----
----
WN2779
WN1833
WN1833
----
----
----
----
----
10:20
----
WN5070
WN1143
WN1143
----
----
----
----
----
----
11:10
WN2744
WN428
WN428
11:55
12:05
12:05
11:55
11:55
----
12:10
WN554
WN1879
WN1879
----
16:10
16:10
----
----
----
----
WN235
WN133
WN133
----
----
----
----
----
16:50
----
WN4616
WN1879
WN1879
17:20
----
----
17:20
17:20
----
----
WN2745
WN1879
WN1879
19:00
17:30
17:30
19:00
19:00
----
----
WN1107
WN1879
WN1879
----
----
----
----
----
----
18:30
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 4h 30m - 8h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
40 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via BNA
BDL
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
WN1708
WN4369
WN4369
----
07:45
07:45
----
----
----
----
WN1775
WN4369
WN4369
07:55
----
----
07:55
07:55
----
08:30
WN1775
WN266
WN266
----
----
----
----
----
08:00
----
WN2959
WN4369
WN4369
----
08:40
08:40
----
----
----
----
WN1257
WN4369
WN4369
09:00
----
----
09:00
09:00
----
----
WN533
WN4369
WN4369
----
----
----
----
----
----
11:50
The timetable & schedule information was updated at 2026-04-21
Via Cleveland with Southwest Airlines
-
Total flight time: 5h 15m - 5h 15m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via CLE
BDL
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
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-21
