Airlines with flights from Chicago to Boston
There are two airlines with scheduled flights between MDW and BOS. Southwest is the only airline with non-stop flights from Midway International Airport to Logan Airport and the flight time is 2 hours and 15 minutes.
There are two airlines with scheduled flights between MDW and BOS. Southwest is the only airline with non-stop flights from Midway International Airport to Logan Airport and the flight time is 2 hours and 15 minutes. Choose airline
Direct
Non-stop
2h 15min
Via Detroit
3h 52min
Via Baltimore
3h 55min
Via Saint Louis
4h 20min
Via Nashville
4h 40min
Via Minneapolis
5h 18min
Via Cleveland
5h 15min
NEW
Starts 06/10
Via Indianapolis
6h 20min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 15 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
41 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
BOS
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
WN4611
07:40
07:40
07:40
07:40
07:40
05:25
05:15
WN1405
09:20
09:00
09:00
09:20
09:20
----
07:40
WN356
----
----
----
----
----
08:15
----
WN3456
----
----
----
----
----
12:00
----
WN1498
----
----
----
----
----
----
12:10
WN4716
12:30
----
----
12:30
12:30
----
----
WN2641
----
12:45
12:45
----
----
----
----
WN4975
16:00
14:40
14:40
16:00
16:00
17:45
13:45
WN1374
----
18:05
18:05
----
----
----
----
WN3521
----
----
----
----
----
----
18:45
WN232
19:35
----
----
19:35
19:35
----
----
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
-
Total flight time: 3h 52m - 6h 03m.
-
Sky Team Alliance
-
Boston is a Delta Air Lines hub.
-
94 flights per week
MDW
Via DTW
BOS
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
DL1171
DL1171
09:17
09:17
09:17
09:17
09:17
09:17
09:17
DL4688
DL1707
DL1707
13:16
13:16
13:16
13:16
13:16
----
13:16
DL4690
DL1187
DL1187
18:58
18:58
18:58
18:58
18:58
18:35
----
The timetable & schedule information was updated at 2026-04-21
Via Baltimore with Southwest Airlines
-
Total flight time: 3h 55m - 8h 35m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
189 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via BWI
BOS
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
WN2706
WN1221
WN1221
----
----
----
----
----
----
05:05
WN2742
WN884
WN884
----
----
----
----
----
05:15
----
WN1120
WN887
WN887
----
06:00
06:00
----
----
----
----
WN2742
WN887
WN887
07:00
----
----
07:00
07:00
----
----
WN1306
WN887
WN887
----
----
----
----
----
----
07:10
WN2731
WN4760
WN4760
----
----
----
----
----
----
07:40
WN748
WN887
WN887
----
----
----
----
----
----
07:45
WN582
WN211
WN211
----
07:45
07:45
----
----
----
----
WN758
WN211
WN211
07:50
07:50
07:50
07:50
07:50
07:45
----
WN174
WN211
WN211
----
----
----
----
----
07:45
----
WN1267
WN211
WN211
07:45
----
----
07:45
07:45
----
----
WN4723
WN211
WN211
07:45
----
----
07:45
07:45
----
----
WN937
WN211
WN211
----
07:50
07:50
----
----
----
----
WN2731
WN211
WN211
----
07:50
07:50
----
----
----
----
WN1695
WN737
WN737
08:05
----
----
08:05
08:05
----
----
WN1355
WN884
WN884
----
08:10
08:10
----
----
----
----
WN925
WN2491
WN2491
----
----
----
----
----
08:25
----
WN4070
WN887
WN887
----
----
----
----
----
----
08:50
WN1355
WN211
WN211
08:55
----
----
08:55
08:55
----
----
WN3877
WN2082
WN2082
----
10:10
10:10
----
----
----
----
WN2779
WN3065
WN3065
----
----
----
----
----
10:20
----
WN5070
WN4760
WN4760
----
----
----
----
----
----
11:10
WN2744
WN737
WN737
11:55
----
----
11:55
11:55
----
----
WN2744
WN2082
WN2082
----
12:05
12:05
----
----
----
----
WN2744
WN2375
WN2375
----
----
----
----
----
----
12:10
WN2848
WN4361
WN4361
12:45
----
----
12:45
12:45
----
----
WN1247
WN4361
WN4361
13:00
----
----
13:00
13:00
----
----
WN1009
WN3065
WN3065
----
----
----
----
----
13:10
----
WN554
WN892
WN892
----
16:10
16:10
----
----
----
----
WN235
WN892
WN892
----
----
----
----
----
16:50
----
WN4616
WN892
WN892
17:20
----
----
17:20
17:20
----
----
WN2745
WN892
WN892
----
17:30
17:30
----
----
----
----
WN1107
WN892
WN892
----
----
----
----
----
----
18:30
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 4h 20m - 6h 45m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
55 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via STL
BOS
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
WN2900
WN4084
WN4084
----
----
----
----
----
06:30
----
WN2900
WN3891
WN3891
07:50
08:20
08:20
07:50
07:50
----
08:05
WN2901
WN3892
WN3892
11:00
10:00
10:00
11:00
11:00
----
----
WN2902
WN3892
WN3892
----
11:25
11:25
----
----
----
----
WN103
WN3892
WN3892
----
----
----
----
----
14:35
----
WN2904
WN2416
WN2416
----
17:10
17:10
----
----
----
----
WN2904
WN4724
WN4724
18:00
----
----
18:00
18:00
----
----
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 4h 40m - 8h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
101 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)
MDW
Via BNA
BOS
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
WN3855
WN4484
WN4484
----
----
----
----
----
----
06:10
WN1053
WN4560
WN4560
----
----
----
----
----
06:40
----
WN2959
WN4560
WN4560
07:15
----
----
07:15
07:15
----
----
WN1708
WN4372
WN4372
----
07:45
07:45
----
----
----
----
WN1775
WN4372
WN4372
07:55
----
----
07:55
07:55
08:00
----
WN1337
WN4484
WN4484
----
----
----
----
----
----
07:55
WN1257
WN4372
WN4372
09:00
----
----
09:00
09:00
----
----
WN2732
WN4372
WN4372
----
----
----
----
----
09:15
----
WN533
WN4372
WN4372
----
----
----
----
----
----
11:50
WN1257
WN459
WN459
----
----
----
----
----
15:30
----
WN3869
WN459
WN459
17:05
----
----
17:05
17:05
----
----
WN1073
WN459
WN459
----
17:20
17:20
----
----
----
18:35
The timetable & schedule information was updated at 2026-04-21
