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Find Deals on Flights 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: Tue Jun 16 2015 Return: Wed Jun 17 2015 Trip spans 2 days
Delta
Delta
MDW
8:30a
BOS
12:15p
3h 45m
1 stop
BOS
3:15a
MDW
12:09p
8h 54m
1 stop
Depart: Tue Jul 28 2015 Return: Wed Aug 26 2015 Trip spans 30 days
Delta
Delta
MDW
3:05a
BOS
8:58a
5h 53m
1 stop
BOS
9:30a
MDW
3:57p
6h 27m
1 stop
Depart: Tue Aug 4 2015 Return: Tue Aug 18 2015 Trip spans 15 days
Delta
Delta
MDW
2:14p
BOS
7:32p
5h 18m
1 stop
BOS
12:33p
MDW
5:27p
4h 54m
1 stop
Depart: Tue Aug 11 2015 Return: Wed Aug 19 2015 Trip spans 9 days
Delta
Delta
MDW
9:53a
BOS
3:28p
5h 35m
1 stop
BOS
3:10a
MDW
9:23a
6h 13m
1 stop
Depart: Tue Aug 18 2015 Return: Tue Aug 25 2015 Trip spans 8 days
Delta
Delta
MDW
1:57p
BOS
7:31p
5h 34m
1 stop
BOS
3:10a
MDW
9:23a
6h 13m
1 stop
Depart: Thu Aug 27 2015 Return: Tue Sep 1 2015 Trip spans 6 days
Delta
Delta
MDW
5:00a
BOS
10:53a
5h 53m
1 stop
BOS
12:35p
MDW
5:15p
4h 40m
1 stop
Depart: Tue Sep 1 2015 Return: Wed Sep 2 2015 Trip spans 2 days
Delta
Delta
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
BOS
10:43a
MDW
2:50p
4h 07m
1 stop
Depart: Mon Sep 14 2015 Return: Wed Sep 16 2015 Trip spans 3 days
Delta
Delta
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
BOS
12:35p
MDW
5:15p
4h 40m
1 stop
Depart: Wed Sep 16 2015 Return: Thu Sep 17 2015 Trip spans 2 days
Delta
Delta
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
BOS
3:10a
MDW
9:15a
6h 05m
1 stop
Depart: Mon Sep 21 2015 Return: Wed Sep 23 2015 Trip spans 3 days
Delta
Delta
MDW
1:55p
BOS
7:25p
5h 30m
1 stop
BOS
10:43a
MDW
2:50p
4h 07m
1 stop
Depart: Tue Sep 22 2015 Return: Tue Sep 29 2015 Trip spans 8 days
Delta
Delta
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
BOS
5:00a
MDW
9:15a
4h 15m
1 stop
Depart: Wed Sep 23 2015 Return: Tue Sep 29 2015 Trip spans 7 days
Delta
Delta
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
BOS
5:00a
MDW
9:15a
4h 15m
1 stop
Depart: Mon Sep 28 2015 Return: Tue Sep 29 2015 Trip spans 2 days
Delta
Delta
MDW
5:15a
BOS
9:02a
3h 47m
1 stop
BOS
5:00a
MDW
9:15a
4h 15m
1 stop
Depart: Wed Sep 30 2015 Return: Sat Oct 3 2015 Trip spans 4 days
Delta
Delta
MDW
8:40a
BOS
12:36p
3h 56m
1 stop
BOS
12:25p
MDW
5:53p
5h 28m
1 stop
Depart: Thu Oct 1 2015 Return: Tue Oct 6 2015 Trip spans 6 days
Delta
Delta
MDW
5:15a
BOS
10:53a
5h 38m
1 stop
BOS
2:00a
MDW
9:15a
7h 15m
1 stop
Depart: Sat Oct 17 2015 Return: Sat Oct 24 2015 Trip spans 8 days
Delta
Delta
MDW
11:10a
BOS
6:11p
7h 01m
1 stop
BOS
12:25p
MDW
5:53p
5h 28m
1 stop
Depart: Thu Oct 29 2015 Return: Sun Nov 1 2015 Trip spans 4 days
Delta
Delta
MDW
5:15a
BOS
10:53a
5h 38m
1 stop
BOS
1:10a
MDW
6:30a
5h 20m
1 stop
Depart: Fri Oct 30 2015 Return: Sun Nov 1 2015 Trip spans 3 days
Delta
Delta
MDW
3:15a
BOS
8:40a
5h 25m
1 stop
BOS
5:30a
MDW
12:10p
6h 40m
1 stop
Depart: Fri Nov 6 2015 Return: Mon Nov 9 2015 Trip spans 4 days
Delta
Delta
MDW
2:00a
BOS
6:00a
4h 00m
1 stop
BOS
6:25a
MDW
12:51p
6h 26m
1 stop
Depart: Sun Aug 9 2015 Return: Sun Aug 16 2015 Trip spans 8 days
Sun Country Air
Sun Country Air
MDW
4:00a
BOS
3:05p
11h 05m
1 stop
BOS
3:20a
MDW
5:45p
14h 25m
1 stop
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
1809 5:30 am 8:40 am Jun 13 - Jun 27
4171 6:55 am 10:05 am Jun 7 - Aug 2
4821 7:25 am 10:35 am Jun 8 - Jul 2
4821 7:25 am 10:35 am Jul 3 - Jul 3
4821 7:25 am 10:35 am Jul 6 - Aug 7
1659 7:35 am 10:50 am May 30 - Jun 6
1851 7:55 am 11:05 am Jun 13 - Jun 27
249 7:55 am 11:05 am Jul 4 - Jul 4
2960 11:40 am 2:55 pm Jul 3 - Jul 3
2960 11:40 am 2:55 pm Jul 5 - Aug 7
2960 11:40 am 2:55 pm Jun 7 - Jul 2
1365 1:20 pm 4:40 pm Jun 13 - Jun 27
3944 1:20 pm 4:35 pm Jun 6 - Jun 6
4534 1:20 pm 4:40 pm Jul 4 - Jul 4
5366 1:40 pm 5:00 pm Jun 7 - Jul 2
5366 1:40 pm 5:00 pm Jul 5 - Aug 7
1865 1:55 pm 5:15 pm Jul 3 - Jul 3
1512 3:20 pm 6:35 pm Jun 6 - Jun 6
1406 4:45 pm 8:00 pm Jun 7 - Jul 2
1406 4:45 pm 8:00 pm Jul 5 - Aug 8
2340 4:45 pm 8:00 pm Jul 3 - Jul 3
2165 5:45 pm 9:00 pm Jun 6 - Jun 6
277 6:10 pm 9:25 pm Jun 7 - Jul 2
277 6:10 pm 9:25 pm Jul 5 - Aug 7
1653 6:25 pm 9:40 pm Jul 3 - Jul 3
1222 6:30 pm 9:45 pm Jun 13 - Jun 27
2152 6:30 pm 9:45 pm Jul 4 - Jul 4
1276 8:40 pm 11:55 pm Jun 6 - Jun 6
2483 9:00 pm 12:10 am Jun 13 - Jun 27
3299 10:00 pm 1:10 am Jun 7 - Jul 2
3299 10:00 pm 1:10 am Jul 5 - Aug 7
Airports
Origin

Chicago
$218
Destination

Boston
$218