Airlines with flights from Hartford to Chicago
There are two airlines with scheduled flights between BDL and MDW. Southwest is the only airline with non-stop flights from Bradley International to Midway International Airport and the flight time is 2 hours and 25 minutes.
There are two airlines with scheduled flights between BDL and MDW. Southwest is the only airline with non-stop flights from Bradley International to Midway International Airport and the flight time is 2 hours and 25 minutes. Choose airline
Direct
Non-stop
2h 25min
Via Detroit
3h 44min
Via Baltimore
4h 5min
Via Nashville
4h 50min
Via Pittsburgh
6h 20min
Via Indianapolis
5h 25min
Starts 04/07
Via Buffalo
5h 55min
NEW
Starts 04/10
Via Columbus
5h 55min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 25 minutes
-
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
BDL
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
WN1102
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----
----
----
----
----
07:05
WN4212
07:55
07:55
07:55
07:55
07:55
07:55
----
WN427
12:40
12:40
12:40
12:40
12:40
----
----
WN428
19:10
18:30
18:30
19:10
19:10
17:55
19:15
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
-
Total flight time: 3h 44m - 6h 16m.
-
Sky Team Alliance
-
50 flights per week
BDL
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
DL2964
DL4684
DL4684
05:25
05:25
05:25
05:25
05:25
05:25
05:25
DL2859
DL4688
DL4688
09:49
09:49
09:49
09:49
09:49
----
09:49
DL2163
DL4677
DL4677
13:15
13:15
13:15
13:15
13:15
13:15
13:15
The timetable & schedule information was updated at 2026-04-21
Via Baltimore with Southwest Airlines
-
Total flight time: 4h 05m - 8h 40m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
135 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
BDL
Via BWI
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
WN4428
WN4217
WN4217
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----
----
----
----
----
05:35
WN420
WN4217
WN4217
05:50
----
----
05:50
05:50
----
----
WN420
WN1139
WN1139
----
05:55
05:55
----
----
----
----
WN420
WN2794
WN2794
----
----
----
----
----
06:00
----
WN4282
WN577
WN577
----
----
----
----
----
----
08:35
WN1031
WN2475
WN2475
----
08:55
08:55
----
----
----
----
WN246
WN938
WN938
----
----
----
----
----
08:55
----
WN421
WN435
WN435
09:00
----
----
09:00
09:00
----
----
WN2731
WN655
WN655
----
----
----
----
----
----
11:30
WN174
WN1539
WN1539
----
----
----
----
----
11:30
----
WN2731
WN1107
WN1107
----
11:40
11:40
----
----
----
----
WN4428
WN961
WN961
12:40
----
----
12:40
12:40
----
----
WN3761
WN914
WN914
----
----
----
----
----
----
13:30
WN423
WN997
WN997
----
14:35
14:35
----
----
----
----
WN423
WN4367
WN4367
14:50
----
----
14:50
14:50
----
----
WN4075
WN998
WN998
----
16:00
16:00
----
----
----
----
WN234
WN375
WN375
----
----
----
----
----
----
17:05
WN4075
WN999
WN999
17:10
----
----
17:10
17:10
17:10
----
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 4h 50m - 7h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
31 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
BDL
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
WN1009
WN481
WN481
----
----
----
----
----
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11:10
WN4472
WN1430
WN1430
----
----
----
----
----
12:45
----
WN4472
WN2241
WN2241
----
12:55
12:55
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
Via Pittsburgh with Southwest Airlines
-
Total flight time: 6h 20m - 6h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
3 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
BDL
Via PIT
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
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-21
