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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: Sat Jun 6 2015 Return: Tue Jun 9 2015 Trip spans 4 days
Delta
Delta
BOS
7:30a
MDW
2:28p
6h 58m
1 stop
MDW
8:30a
BOS
12:15p
3h 45m
1 stop
Depart: Tue Jun 9 2015 Return: Wed Jun 10 2015 Trip spans 2 days
Delta
Delta
BOS
3:09a
MDW
9:25a
6h 16m
1 stop
MDW
5:10a
BOS
10:52a
5h 42m
1 stop
Depart: Wed Jun 10 2015 Return: Tue Jun 23 2015 Trip spans 14 days
Delta
Delta
BOS
9:30a
MDW
3:53p
6h 23m
1 stop
MDW
9:50a
BOS
3:28p
5h 38m
1 stop
Depart: Tue Aug 25 2015 Return: Sat Sep 12 2015 Trip spans 19 days
Delta
Delta
BOS
2:10a
MDW
7:30a
5h 20m
1 stop
MDW
3:15a
BOS
8:40a
5h 25m
1 stop
Depart: Tue Sep 1 2015 Return: Tue Sep 8 2015 Trip spans 8 days
Delta
Delta
BOS
10:43a
MDW
2:50p
4h 07m
1 stop
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
Depart: Wed Sep 2 2015 Return: Tue Sep 8 2015 Trip spans 7 days
Delta
Delta
BOS
10:43a
MDW
2:50p
4h 07m
1 stop
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
Depart: Sat Sep 5 2015 Return: Tue Sep 8 2015 Trip spans 4 days
Delta
Delta
BOS
2:00a
MDW
6:25a
4h 25m
1 stop
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
Depart: Wed Sep 30 2015 Return: Sat Oct 3 2015 Trip spans 4 days
Delta
Delta
BOS
3:15a
MDW
8:49a
5h 34m
1 stop
MDW
1:10p
BOS
6:41p
5h 31m
1 stop
Depart: Sat Oct 3 2015 Return: Tue Oct 6 2015 Trip spans 4 days
Delta
Delta
BOS
2:00a
MDW
6:25a
4h 25m
1 stop
MDW
3:00a
BOS
7:00a
4h 00m
1 stop
Depart: Tue Oct 6 2015 Return: Wed Oct 14 2015 Trip spans 9 days
Delta
Delta
BOS
12:35p
MDW
5:15p
4h 40m
1 stop
MDW
8:40a
BOS
12:36p
3h 56m
1 stop
Depart: Wed Oct 7 2015 Return: Tue Oct 13 2015 Trip spans 7 days
Delta
Delta
BOS
5:00a
MDW
9:15a
4h 15m
1 stop
MDW
2:30p
BOS
6:32p
4h 02m
1 stop
Depart: Thu Sep 10 2015 Return: Tue Sep 15 2015 Trip spans 6 days
Delta
Delta
BOS
9:30a
MDW
3:33p
6h 03m
1 stop
MDW
8:40a
BOS
12:36p
3h 56m
1 stop
Depart: Sat Sep 12 2015 Return: Mon Sep 14 2015 Trip spans 3 days
Delta
Delta
BOS
2:00a
MDW
6:25a
4h 25m
1 stop
MDW
5:15a
BOS
12:36p
7h 21m
1 stop
Depart: Wed Sep 16 2015 Return: Mon Sep 21 2015 Trip spans 6 days
Delta
Delta
BOS
8:30a
MDW
1:10p
4h 40m
1 stop
MDW
8:40a
BOS
12:36p
3h 56m
1 stop
Depart: Wed Oct 21 2015 Return: Mon Oct 26 2015 Trip spans 6 days
Delta
Delta
BOS
3:15a
MDW
8:49a
5h 34m
1 stop
MDW
8:40a
BOS
12:36p
3h 56m
1 stop
Depart: Sat Oct 24 2015 Return: Mon Oct 26 2015 Trip spans 3 days
Delta
Delta
BOS
2:00a
MDW
6:25a
4h 25m
1 stop
MDW
7:05a
BOS
11:54a
4h 49m
1 stop
Depart: Sun Sep 6 2015 Return: Tue Sep 8 2015 Trip spans 3 days
Delta
Delta
BOS
2:00a
MDW
6:00a
4h 00m
1 stop
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
Depart: Sun Sep 13 2015 Return: Wed Sep 16 2015 Trip spans 4 days
Delta
Delta
BOS
2:10a
MDW
7:30a
5h 20m
1 stop
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
Depart: Tue Nov 3 2015 Return: Fri Nov 6 2015 Trip spans 4 days
Delta
Delta
BOS
11:35a
MDW
4:15p
4h 40m
1 stop
MDW
4:15a
BOS
9:53a
5h 38m
1 stop
Depart: Thu Jul 2 2015 Return: Sat Jul 4 2015 Trip spans 3 days
Sun Country Air
Sun Country Air
BOS
7:45a
MDW
5:45p
10h 00m
1 stop
MDW
4:00a
BOS
6:15p
14h 15m
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
1661 5:30 am 7:15 am Jun 13 - Jun 13
1661 5:30 am 7:15 am Jun 20 - Jun 27
527 5:30 am 7:10 am Jun 7 - Jul 2
604 5:40 am 7:30 am May 21 - May 29
604 5:40 am 7:30 am May 31 - Jun 5
643 5:55 am 7:55 am May 30 - Jun 6
665 8:25 am 10:05 am Jun 7 - Jul 2
1755 8:30 am 10:10 am Jun 13 - Jun 27
2093 9:05 am 10:45 am May 30 - Jun 6
2229 11:10 am 12:50 pm May 26 - Jun 5
2669 11:45 am 1:25 pm May 30 - Jun 6
3036 12:45 pm 2:20 pm Jun 7 - Jul 2
2 1:35 pm 3:10 pm Jun 13 - Jun 27
1298 3:40 pm 5:25 pm Jun 13 - Jun 27
2506 3:50 pm 5:35 pm May 30 - Jun 6
383 5:00 pm 6:50 pm Jun 7 - Aug 7
4207 5:05 pm 6:50 pm May 31 - Jun 5
4207 5:05 pm 6:50 pm May 21 - May 29
585 8:10 pm 9:50 pm May 31 - Jun 5
585 8:10 pm 9:50 pm May 21 - May 29
4429 8:35 pm 10:20 pm Jun 7 - Jul 2
5474 8:40 pm 10:20 pm Jun 13 - Jun 27
1476 9:40 pm 11:25 pm Jun 13 - Jun 27
413 9:55 pm 11:35 pm Jun 7 - Jul 2
Airports
Origin

Boston
$218
Destination

Chicago
$218