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 30 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 30 minutes. Choose airline
Direct
Non-stop
2h 30min
Via Detroit
3h 44min
Via Baltimore
4h 5min
Via Nashville
4h 50min
Via Pittsburgh
6h 20min
Via Indianapolis
5h 25min
Via Buffalo
5h 55min
NEW
Starts 04/10
Via Columbus
5h 55min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 30 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
19 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BDL
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
WN423
----
07:45
07:45
----
----
----
07:50
WN554
----
----
----
----
----
07:55
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WN4212
07:55
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----
----
----
----
----
WN473
----
----
----
08:00
08:00
----
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WN512
----
----
----
----
----
----
11:20
WN427
12:40
----
----
----
----
----
----
WN875
----
12:45
12:45
----
----
----
----
WN1070
----
----
----
13:40
13:40
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WN1339
----
----
----
----
----
15:45
----
WN425
----
17:55
17:55
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----
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18:20
WN1459
----
----
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18:20
18:20
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WN428
19:10
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----
----
----
----
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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
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
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 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BDL
Via BWI
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
WN417
WN1683
WN1683
----
----
----
----
----
----
05:20
WN417
WN4094
WN4094
----
----
----
----
----
05:50
----
WN420
WN4217
WN4217
05:50
----
----
----
----
----
----
WN667
WN992
WN992
----
----
----
05:55
05:55
----
----
WN1451
WN991
WN991
----
08:10
08:10
----
----
----
----
WN429
WN915
WN915
----
----
----
----
----
08:25
----
WN866
WN991
WN991
----
----
----
----
----
----
09:00
WN421
WN435
WN435
09:00
----
----
----
----
----
----
WN1967
WN1195
WN1195
----
----
----
10:15
10:15
----
----
WN105
WN1064
WN1064
----
----
----
----
----
11:45
----
WN908
WN450
WN450
----
----
----
----
----
----
12:00
WN105
WN3863
WN3863
----
----
----
12:35
12:35
----
----
WN4428
WN961
WN961
12:40
----
----
----
----
----
----
WN105
WN992
WN992
----
12:40
12:40
----
----
----
----
WN423
WN4367
WN4367
14:50
----
----
----
----
----
----
WN437
WN1195
WN1195
----
15:05
15:05
----
----
----
----
WN437
WN4821
WN4821
----
----
----
----
----
15:20
----
WN2006
WN4094
WN4094
----
----
----
15:40
15:40
----
----
WN4075
WN999
WN999
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 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BDL
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
WN1397
WN577
WN577
----
16:45
16:45
----
----
----
----
WN1045
WN4549
WN4549
----
----
----
17:00
17:00
----
----
WN579
WN577
WN577
----
----
----
----
----
----
17:50
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 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BDL
Via PIT
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
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2026-04-21
