Airlines with flights from Boston to Chicago
There are two airlines with scheduled flights between BOS and MDW. Southwest is the only airline with non-stop flights from Logan Airport to Midway International Airport and the flight time is 2 hours and 45 minutes.
There are two airlines with scheduled flights between BOS and MDW. Southwest is the only airline with non-stop flights from Logan Airport to Midway International Airport and the flight time is 2 hours and 45 minutes. Choose airline
Direct
Non-stop
2h 45min
Via Detroit
4h 3min
Via Baltimore
4h 15min
Via Saint Louis
4h 30min
Via Nashville
5h 10min
Via Minneapolis
5h 51min
Via Pittsburgh
5h 45min
NEW
Starts 01/10
Via Cleveland
5h 35min
NEW
Starts 03/10
Via Indianapolis
8h 0min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 45 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
42 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BOS
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
WN3239
05:25
----
----
05:25
05:25
05:20
----
WN3054
----
05:35
05:35
----
----
----
----
WN745
07:30
07:30
07:30
07:30
07:30
07:55
07:20
WN746
13:10
----
----
13:10
13:10
14:10
12:55
WN320
----
13:25
13:25
----
----
----
----
WN4106
16:45
15:45
15:45
16:45
16:45
----
----
WN2777
----
----
----
----
----
----
16:45
WN3911
18:45
17:30
17:30
18:45
18:45
17:45
----
WN3287
----
----
----
----
----
----
19:05
WN585
----
----
----
----
----
----
22:05
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
-
Total flight time: 4h 03m - 6h 23m.
-
Sky Team Alliance
-
Boston is a Delta Air Lines hub.
-
69 flights per week
BOS
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
DL1019
DL4684
DL4684
05:30
05:30
05:30
05:30
05:30
05:30
05:30
DL1748
DL4688
DL4688
09:15
09:15
09:15
09:15
09:15
09:15
09:15
DL2222
DL4677
DL4677
13:10
13:10
13:10
13:10
13:10
13:10
13:10
The timetable & schedule information was updated at 2026-04-21
Via Baltimore with Southwest Airlines
-
Total flight time: 4h 15m - 8h 55m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
128 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BOS
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
WN727
WN2794
WN2794
----
----
----
----
----
05:10
----
WN727
WN995
WN995
----
05:25
05:25
----
----
----
----
WN727
WN4217
WN4217
05:45
----
----
05:45
05:45
----
05:30
WN487
WN2794
WN2794
----
----
----
----
----
07:15
----
WN732
WN577
WN577
----
----
----
----
----
----
07:45
WN732
WN914
WN914
----
08:55
08:55
----
----
----
----
WN732
WN435
WN435
09:10
----
----
09:10
09:10
----
----
WN2640
WN655
WN655
----
----
----
----
----
----
11:35
WN3038
WN1107
WN1107
----
11:35
11:35
----
----
----
----
WN733
WN2693
WN2693
----
----
----
----
----
12:35
----
WN733
WN997
WN997
13:20
----
----
13:20
13:20
----
----
WN2247
WN997
WN997
----
14:25
14:25
----
----
----
----
WN2342
WN4355
WN4355
----
----
----
----
----
----
14:30
WN1101
WN998
WN998
----
----
----
----
----
15:05
----
WN1053
WN998
WN998
15:55
----
----
15:55
15:55
----
----
WN1898
WN999
WN999
17:20
17:00
17:00
17:20
17:20
16:50
----
WN1898
WN2730
WN2730
----
----
----
----
----
----
20:15
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 4h 30m - 6h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
49 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BOS
Via STL
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
WN752
WN2570
WN2570
05:35
----
----
05:35
05:35
----
05:50
WN752
WN2665
WN2665
----
05:50
05:50
----
----
----
----
WN4917
WN556
WN556
12:55
12:50
12:50
12:55
12:55
----
14:15
WN4917
WN2468
WN2468
----
----
----
----
----
13:15
----
WN754
WN3957
WN3957
18:50
18:25
18:25
18:50
18:50
----
18:50
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 5h 10m - 9h 05m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
61 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
BOS
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
WN724
WN1430
WN1430
----
08:45
08:45
----
----
----
----
WN724
WN1009
WN1009
----
----
----
----
----
----
09:05
WN2338
WN578
WN578
20:00
18:50
18:50
20:00
20:00
19:10
20:00
The timetable & schedule information was updated at 2026-04-21
