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Find Flight Deals from Boston Logan International to Chicago Midway (BOS - MDW)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Boston Logan International to Chicago Midway

(Round-trip)
Depart: Tue Apr 14 2015 Return: Wed Apr 15 2015 Trip spans 2 days
Delta
Delta
BOS
12:08p
MDW
6:17p
6h 09m
1 stop
MDW
3:00a
BOS
8:57a
5h 57m
1 stop
Depart: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
Delta
Delta
BOS
2:50p
MDW
6:45p
3h 55m
1 stop
MDW
11:07a
BOS
4:02p
4h 55m
1 stop
Depart: Thu Apr 23 2015 Return: Tue Apr 28 2015 Trip spans 6 days
Delta
Delta
BOS
7:33a
MDW
1:35p
6h 02m
1 stop
MDW
5:20a
BOS
12:00p
6h 40m
1 stop
Depart: Mon Apr 27 2015 Return: Wed Apr 29 2015 Trip spans 3 days
Delta
Delta
BOS
12:45p
MDW
6:45p
6h 00m
1 stop
MDW
3:00a
BOS
6:54a
3h 54m
1 stop
Depart: Tue Apr 28 2015 Return: Wed Apr 29 2015 Trip spans 2 days
Delta
Delta
BOS
3:15a
MDW
8:41a
5h 26m
1 stop
MDW
3:00a
BOS
6:54a
3h 54m
1 stop
Depart: Wed Apr 29 2015 Return: Mon May 4 2015 Trip spans 6 days
Delta
Delta
BOS
1:40a
MDW
5:43a
4h 03m
1 stop
MDW
11:12a
BOS
4:03p
4h 51m
1 stop
Depart: Thu Apr 30 2015 Return: Mon May 4 2015 Trip spans 5 days
Delta
Delta
BOS
4:45a
MDW
9:20a
4h 35m
1 stop
MDW
11:12a
BOS
4:03p
4h 51m
1 stop
Depart: Fri May 1 2015 Return: Mon May 11 2015 Trip spans 11 days
Delta
Delta
BOS
1:40a
MDW
5:50a
4h 10m
1 stop
MDW
11:12a
BOS
6:03p
6h 51m
1 stop
Depart: Sat May 2 2015 Return: Mon May 4 2015 Trip spans 3 days
Delta
Delta
BOS
10:45a
MDW
7:07p
8h 22m
1 stop
MDW
11:12a
BOS
4:03p
4h 51m
1 stop
Depart: Mon May 4 2015 Return: Tue May 5 2015 Trip spans 2 days
Delta
Delta
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
MDW
5:25a
BOS
8:59a
3h 34m
1 stop
Depart: Tue May 5 2015 Return: Wed May 6 2015 Trip spans 2 days
Delta
Delta
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
MDW
3:10a
BOS
6:53a
3h 43m
1 stop
Depart: Wed May 6 2015 Return: Mon May 11 2015 Trip spans 6 days
Delta
Delta
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
MDW
2:35p
BOS
6:20p
3h 45m
1 stop
Depart: Thu May 7 2015 Return: Sat May 9 2015 Trip spans 3 days
Delta
Delta
BOS
1:55a
MDW
7:27a
5h 32m
1 stop
MDW
2:45a
BOS
10:17a
7h 32m
1 stop
Depart: Fri May 8 2015 Return: Mon May 11 2015 Trip spans 4 days
Delta
Delta
BOS
6:05a
MDW
12:56p
6h 51m
1 stop
MDW
2:35p
BOS
6:20p
3h 45m
1 stop
Depart: Sat May 9 2015 Return: Mon May 11 2015 Trip spans 3 days
Delta
Delta
BOS
1:40a
MDW
6:22a
4h 42m
1 stop
MDW
12:34p
BOS
6:20p
5h 46m
1 stop
Depart: Mon May 11 2015 Return: Tue May 12 2015 Trip spans 2 days
Delta
Delta
BOS
1:20p
MDW
7:09p
5h 49m
1 stop
MDW
11:12a
BOS
4:03p
4h 51m
1 stop
Depart: Tue May 12 2015 Return: Wed May 13 2015 Trip spans 2 days
Delta
Delta
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
MDW
3:10a
BOS
6:53a
3h 43m
1 stop
Depart: Wed May 13 2015 Return: Tue May 19 2015 Trip spans 7 days
Delta
Delta
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
MDW
8:35a
BOS
12:21p
3h 46m
1 stop
Depart: Thu May 14 2015 Return: Tue May 19 2015 Trip spans 6 days
Delta
Delta
BOS
6:05a
MDW
12:56p
6h 51m
1 stop
MDW
3:10a
BOS
6:55a
3h 45m
1 stop
Depart: Wed Aug 19 2015 Return: Mon Aug 24 2015 Trip spans 6 days
Sun Country Air
Sun Country Air
BOS
7:45a
MDW
5:45p
10h 00m
1 stop
MDW
4:00a
BOS
3:05p
11h 05m
1 stop
Select an airline:  Southwest
Direct flights BOS to MDW on Southwest
Flight # Depart BOS Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
604 5:40 am 7:30 am Apr 12 - May 15
604 5:40 am 7:30 am Apr 8 - Apr 10
643 5:55 am 7:55 am Apr 11 - May 16
2093 9:05 am 10:45 am Apr 11 - May 16
2229 11:10 am 12:50 pm Apr 8 - May 20
2669 11:45 am 1:25 pm Apr 11 - May 16
2506 3:50 pm 5:35 pm Apr 11 - May 16
4207 5:05 pm 6:50 pm Apr 8 - May 22
585 8:10 pm 9:50 pm Apr 12 - May 22
585 8:10 pm 9:50 pm Apr 8 - Apr 10
Airports
Origin

Boston
$184
Destination

Chicago
$184