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

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

Book cheap flights from Chicago Midway to Boston Logan International

(Round-trip)
Depart: Fri Dec 26 2014 Return: Thu Jan 1 2015 Trip spans 7 days
Delta
Delta
MDW
5:30a
BOS
11:13a
5h 43m
1 stop
BOS
1:00a
MDW
9:21a
8h 21m
1 stop
Depart: Wed Jan 7 2015 Return: Tue Jan 13 2015 Trip spans 7 days
Delta
Delta
MDW
7:30a
BOS
11:33a
4h 03m
1 stop
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
Depart: Tue Jan 13 2015 Return: Wed Jan 14 2015 Trip spans 2 days
Delta
Delta
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
BOS
3:50a
MDW
8:24a
4h 34m
1 stop
Depart: Wed Jan 14 2015 Return: Sat Jan 17 2015 Trip spans 4 days
Delta
Delta
MDW
6:01a
BOS
11:11a
5h 10m
1 stop
BOS
1:00a
MDW
7:05a
6h 05m
1 stop
Depart: Tue Jan 20 2015 Return: Tue Jan 27 2015 Trip spans 8 days
Delta
Delta
MDW
7:30a
BOS
11:38a
4h 08m
1 stop
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
Depart: Wed Jan 21 2015 Return: Thu Jan 22 2015 Trip spans 2 days
Delta
Delta
MDW
7:30a
BOS
1:22p
5h 52m
1 stop
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
Depart: Thu Jan 22 2015 Return: Sat Jan 24 2015 Trip spans 3 days
Delta
Delta
MDW
2:10a
BOS
8:01a
5h 51m
1 stop
BOS
4:00a
MDW
8:37a
4h 37m
1 stop
Depart: Fri Jan 23 2015 Return: Sun Jan 25 2015 Trip spans 3 days
Delta
Delta
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
BOS
11:38a
MDW
4:30p
4h 52m
1 stop
Depart: Sat Jan 24 2015 Return: Mon Jan 26 2015 Trip spans 3 days
Delta
Delta
MDW
7:05a
BOS
2:18p
7h 13m
1 stop
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
Depart: Sun Jan 25 2015 Return: Sun Feb 1 2015 Trip spans 8 days
Delta
Delta
MDW
7:05a
BOS
12:51p
5h 46m
1 stop
BOS
1:00a
MDW
7:06a
6h 06m
1 stop
Depart: Tue Jan 27 2015 Return: Wed Jan 28 2015 Trip spans 2 days
Delta
Delta
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
BOS
11:38a
MDW
4:30p
4h 52m
1 stop
Depart: Wed Jan 28 2015 Return: Wed Feb 4 2015 Trip spans 8 days
Delta
Delta
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
BOS
3:50a
MDW
8:24a
4h 34m
1 stop
Depart: Thu Jan 29 2015 Return: Fri Jan 30 2015 Trip spans 2 days
Delta
Delta
MDW
4:00a
BOS
9:53a
5h 53m
1 stop
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
Depart: Fri Jan 30 2015 Return: Sat Jan 31 2015 Trip spans 2 days
Delta
Delta
MDW
6:01a
BOS
11:11a
5h 10m
1 stop
BOS
3:00a
MDW
9:03a
6h 03m
1 stop
Depart: Sat Jan 31 2015 Return: Mon Feb 2 2015 Trip spans 3 days
Delta
Delta
MDW
12:00p
BOS
5:28p
5h 28m
1 stop
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
Depart: Sun Feb 1 2015 Return: Tue Feb 3 2015 Trip spans 3 days
Delta
Delta
MDW
4:00a
BOS
8:15a
4h 15m
1 stop
BOS
1:00a
MDW
7:53a
6h 53m
1 stop
Depart: Mon Feb 2 2015 Return: Mon Feb 9 2015 Trip spans 8 days
Delta
Delta
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
Depart: Tue Feb 3 2015 Return: Wed Feb 4 2015 Trip spans 2 days
Delta
Delta
MDW
6:01a
BOS
11:11a
5h 10m
1 stop
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
Depart: Wed Feb 4 2015 Return: Thu Feb 5 2015 Trip spans 2 days
Delta
Delta
MDW
4:51a
BOS
10:30a
5h 39m
1 stop
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
Depart: Thu Feb 5 2015 Return: Fri Feb 6 2015 Trip spans 2 days
Delta
Delta
MDW
2:10a
BOS
8:01a
5h 51m
1 stop
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
Change your search
Select an airline:  Southwest
Direct flights MDW to BOS on Southwest
Flight # Depart MDW Arrive BOS Sun Mon Tue Wed Thu Fri Sat Valid Between
1089 6:45 am 10:00 am Dec 29 - Jan 5
2494 7:30 am 10:45 am Jan 27 - Feb 23
2494 7:30 am 10:45 am Jan 16 - Jan 26
2494 7:30 am 10:45 am Jan 6 - Jan 12
3042 7:35 am 10:45 am Jan 10 - Feb 28
1889 8:00 am 11:10 am Dec 20 - Dec 27
1889 8:00 am 11:10 am Dec 28 - Dec 28
3859 1:20 pm 4:35 pm Dec 31 - Dec 31
3859 1:20 pm 4:35 pm Dec 29 - Jan 5
4141 1:20 pm 4:35 pm Jan 1 - Jan 1
749 1:20 pm 4:35 pm Jan 6 - Jan 30
3947 1:25 pm 4:40 pm Dec 26 - Dec 28
3492 1:40 pm 4:55 pm Jan 10 - Jan 24
579 3:25 pm 6:35 pm Dec 26 - Dec 28
3296 3:35 pm 6:45 pm Jan 4 - Jan 4
722 3:35 pm 6:45 pm Jan 1 - Jan 1
2376 3:40 pm 6:50 pm Jan 5 - Jan 5
3784 3:40 pm 6:50 pm Jan 3 - Jan 3
4896 3:40 pm 6:50 pm Dec 29 - Jan 2
2750 4:20 pm 7:30 pm Dec 31 - Dec 31
3920 8:20 pm 11:30 pm Jan 10 - Feb 7
972 9:05 pm 12:20 am Jan 6 - Mar 6
2115 9:15 pm 12:20 am Dec 31 - Dec 31
2895 9:15 pm 12:25 am Dec 21 - Dec 28
455 9:15 pm 12:20 am Dec 29 - Jan 2
455 9:15 pm 12:20 am Jan 3 - Jan 3
455 9:15 pm 12:20 am Jan 4 - Jan 4
455 9:15 pm 12:20 am Jan 1 - Jan 1
455 9:15 pm 12:20 am Jan 5 - Jan 5
Airports
Origin

Chicago
$184
Destination

Boston
$184
Airlines