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Find Deals on Flights 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 Jul 28 2015 Return: Tue Aug 4 2015 Trip spans 8 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
2:35p
BOS
6:31p
3h 56m
1 stop
Depart: Tue Aug 4 2015 Return: Tue Aug 11 2015 Trip spans 8 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
2:35p
BOS
6:31p
3h 56m
1 stop
Depart: Tue Aug 11 2015 Return: Wed Aug 19 2015 Trip spans 9 days
Delta
Delta
BOS
3:10a
MDW
9:23a
6h 13m
1 stop
MDW
5:55a
BOS
11:26a
5h 31m
1 stop
Depart: Tue Aug 18 2015 Return: Tue Aug 25 2015 Trip spans 8 days
Delta
Delta
BOS
5:06a
MDW
9:23a
4h 17m
1 stop
MDW
5:00a
BOS
10:53a
5h 53m
1 stop
Depart: Wed Aug 19 2015 Return: Mon Aug 24 2015 Trip spans 6 days
Delta
Delta
BOS
5:06a
MDW
9:23a
4h 17m
1 stop
MDW
2:35p
BOS
6:21p
3h 46m
1 stop
Depart: Mon Aug 24 2015 Return: Mon Aug 31 2015 Trip spans 8 days
Delta
Delta
BOS
5:06a
MDW
9:23a
4h 17m
1 stop
MDW
2:35p
BOS
6:21p
3h 46m
1 stop
Depart: Tue Aug 25 2015 Return: Mon Aug 31 2015 Trip spans 7 days
Delta
Delta
BOS
10:40a
MDW
2:55p
4h 15m
1 stop
MDW
2:35p
BOS
6:21p
3h 46m
1 stop
Depart: Wed Aug 26 2015 Return: Mon Aug 31 2015 Trip spans 6 days
Delta
Delta
BOS
8:05a
MDW
2:22p
6h 17m
1 stop
MDW
8:31a
BOS
12:20p
3h 49m
1 stop
Depart: Thu Aug 27 2015 Return: Mon Aug 31 2015 Trip spans 5 days
Delta
Delta
BOS
5:06a
MDW
9:23a
4h 17m
1 stop
MDW
2:35p
BOS
6:21p
3h 46m
1 stop
Depart: Fri Aug 28 2015 Return: Mon Aug 31 2015 Trip spans 4 days
Delta
Delta
BOS
12:00p
MDW
7:12p
7h 12m
1 stop
MDW
2:35p
BOS
6:21p
3h 46m
1 stop
Depart: Sat Aug 29 2015 Return: Tue Sep 1 2015 Trip spans 4 days
Delta
Delta
BOS
3:15a
MDW
11:51a
8h 36m
1 stop
MDW
2:00a
BOS
7:40a
5h 40m
1 stop
Depart: Sun Aug 30 2015 Return: Wed Sep 9 2015 Trip spans 11 days
Delta
Delta
BOS
2:14a
MDW
8:49a
6h 35m
1 stop
MDW
1:59p
BOS
7:28p
5h 29m
1 stop
Depart: Tue Sep 1 2015 Return: Sat Sep 5 2015 Trip spans 5 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
12:35p
BOS
4:59p
4h 24m
1 stop
Depart: Wed Sep 2 2015 Return: Sat Sep 5 2015 Trip spans 4 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
12:35p
BOS
4:59p
4h 24m
1 stop
Depart: Fri Sep 4 2015 Return: Sun Sep 6 2015 Trip spans 3 days
Delta
Delta
BOS
3:10a
MDW
9:23a
6h 13m
1 stop
MDW
2:00a
BOS
7:36a
5h 36m
1 stop
Depart: Sat Sep 5 2015 Return: Tue Sep 8 2015 Trip spans 4 days
Delta
Delta
BOS
7:00a
MDW
2:22p
7h 22m
1 stop
MDW
3:00a
BOS
6:54a
3h 54m
1 stop
Depart: Tue Sep 8 2015 Return: Thu Sep 10 2015 Trip spans 3 days
Delta
Delta
BOS
3:10a
MDW
9:23a
6h 13m
1 stop
MDW
6:25a
BOS
1:19p
6h 54m
1 stop
Depart: Wed Sep 9 2015 Return: Sat Sep 12 2015 Trip spans 4 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
11:20a
BOS
4:53p
5h 33m
1 stop
Depart: Thu Sep 10 2015 Return: Fri Sep 11 2015 Trip spans 2 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
8:26a
BOS
12:20p
3h 54m
1 stop
Depart: Fri Sep 11 2015 Return: Sun Sep 13 2015 Trip spans 3 days
Delta
Delta
BOS
9:30a
MDW
5:12p
7h 42m
1 stop
MDW
2:00a
BOS
7:40a
5h 40m
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
1554 5:30 am 7:20 am Aug 9 - Aug 30
1661 5:30 am 7:15 am Jul 11 - Aug 8
527 5:30 am 7:10 am Jul 10 - Aug 7
6526 5:30 am 7:20 am Aug 10 - Sep 4
665 8:25 am 10:05 am Jul 10 - Aug 7
1755 8:30 am 10:10 am Jul 11 - Aug 8
669 9:15 am 11:00 am Aug 9 - Sep 6
1025 11:55 am 1:40 pm Aug 9 - Sep 4
438 12:50 pm 2:25 pm Jul 5 - Aug 7
2 1:35 pm 3:10 pm Jul 11 - Aug 8
1298 3:40 pm 5:25 pm Jul 11 - Aug 1
4535 3:40 pm 5:25 pm Aug 8 - Aug 8
514 4:30 pm 6:20 pm Aug 9 - Sep 4
383 5:00 pm 6:50 pm Jun 28 - Aug 7
4429 8:35 pm 10:20 pm Jul 12 - Aug 7
5474 8:40 pm 10:25 pm Aug 8 - Aug 8
5474 8:40 pm 10:20 pm Jul 11 - Aug 1
2581 8:55 pm 10:40 pm Aug 9 - Sep 4
1476 9:40 pm 11:25 pm Jul 11 - Aug 8
413 9:55 pm 11:35 pm Jul 10 - Aug 7
Airports
Origin

Boston
$206
Destination

Chicago
$206
Airlines