Browse Origins:
Browse Destinations:

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: Wed Apr 15 2015 Return: Wed Apr 22 2015 Trip spans 8 days
Delta
Delta
MDW
3:00a
BOS
8:57a
5h 57m
1 stop
BOS
3:00a
MDW
9:20a
6h 20m
1 stop
Depart: Mon Apr 20 2015 Return: Wed Apr 22 2015 Trip spans 3 days
Delta
Delta
MDW
5:20a
BOS
8:57a
3h 37m
1 stop
BOS
3:00a
MDW
9:20a
6h 20m
1 stop
Depart: Tue Apr 21 2015 Return: Wed Apr 22 2015 Trip spans 2 days
Delta
Delta
MDW
3:00a
BOS
6:54a
3h 54m
1 stop
BOS
2:50p
MDW
6:45p
3h 55m
1 stop
Depart: Tue Apr 28 2015 Return: Wed Apr 29 2015 Trip spans 2 days
Delta
Delta
MDW
5:20a
BOS
12:00p
6h 40m
1 stop
BOS
8:35a
MDW
12:55p
4h 20m
1 stop
Depart: Wed Apr 29 2015 Return: Fri May 1 2015 Trip spans 3 days
Delta
Delta
MDW
8:55a
BOS
2:02p
5h 07m
1 stop
BOS
1:40a
MDW
5:50a
4h 10m
1 stop
Depart: Thu Apr 30 2015 Return: Sat May 2 2015 Trip spans 3 days
Delta
Delta
MDW
5:08a
BOS
11:56a
6h 48m
1 stop
BOS
1:55a
MDW
7:26a
5h 31m
1 stop
Depart: Mon May 4 2015 Return: Tue May 5 2015 Trip spans 2 days
Delta
Delta
MDW
2:35p
BOS
6:20p
3h 45m
1 stop
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
Depart: Tue May 5 2015 Return: Wed May 6 2015 Trip spans 2 days
Delta
Delta
MDW
8:35a
BOS
12:21p
3h 46m
1 stop
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
Depart: Wed May 6 2015 Return: Fri May 8 2015 Trip spans 3 days
Delta
Delta
MDW
8:35a
BOS
12:21p
3h 46m
1 stop
BOS
4:10a
MDW
11:42a
7h 32m
1 stop
Depart: Sat May 9 2015 Return: Mon May 11 2015 Trip spans 3 days
Delta
Delta
MDW
2:45a
BOS
10:17a
7h 32m
1 stop
BOS
1:20p
MDW
7:09p
5h 49m
1 stop
Depart: Mon May 11 2015 Return: Tue May 12 2015 Trip spans 2 days
Delta
Delta
MDW
11:12a
BOS
6:03p
6h 51m
1 stop
BOS
10:32a
MDW
3:56p
5h 24m
1 stop
Depart: Tue May 12 2015 Return: Wed May 13 2015 Trip spans 2 days
Delta
Delta
MDW
1:09p
BOS
6:03p
4h 54m
1 stop
BOS
10:30a
MDW
2:55p
4h 25m
1 stop
Depart: Wed May 13 2015 Return: Sat May 16 2015 Trip spans 4 days
Delta
Delta
MDW
8:35a
BOS
12:21p
3h 46m
1 stop
BOS
1:40a
MDW
6:22a
4h 42m
1 stop
Depart: Tue May 19 2015 Return: Wed May 27 2015 Trip spans 9 days
Delta
Delta
MDW
2:35p
BOS
6:20p
3h 45m
1 stop
BOS
2:50p
MDW
6:43p
3h 53m
1 stop
Depart: Wed May 20 2015 Return: Sat May 23 2015 Trip spans 4 days
Delta
Delta
MDW
3:10a
BOS
6:53a
3h 43m
1 stop
BOS
1:40a
MDW
6:22a
4h 42m
1 stop
Depart: Sat May 23 2015 Return: Tue May 26 2015 Trip spans 4 days
Delta
Delta
MDW
12:30p
BOS
4:41p
4h 11m
1 stop
BOS
12:50p
MDW
6:43p
5h 53m
1 stop
Depart: Sun May 24 2015 Return: Tue May 26 2015 Trip spans 3 days
Delta
Delta
MDW
2:45a
BOS
8:09a
5h 24m
1 stop
BOS
12:50p
MDW
6:43p
5h 53m
1 stop
Depart: Wed May 27 2015 Return: Sat May 30 2015 Trip spans 4 days
Delta
Delta
MDW
8:35a
BOS
12:21p
3h 46m
1 stop
BOS
5:45a
MDW
2:22p
8h 37m
1 stop
Depart: Wed Jun 10 2015 Return: Tue Jun 16 2015 Trip spans 7 days
Delta
Delta
MDW
9:50a
BOS
3:14p
5h 24m
1 stop
BOS
3:10a
MDW
9:24a
6h 14m
1 stop
Depart: Fri Jul 3 2015 Return: Mon Jul 6 2015 Trip spans 4 days
Sun Country Air
Sun Country Air
MDW
4:00a
BOS
3:05p
11h 05m
1 stop
BOS
7:45a
MDW
5:45p
10h 00m
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
331 7:20 am 10:30 am Apr 8 - May 22
1659 7:35 am 10:50 am Apr 11 - May 16
313 1:15 pm 4:30 pm Apr 8 - May 22
3944 1:20 pm 4:35 pm Apr 18 - May 16
3944 1:20 pm 4:35 pm Apr 11 - Apr 11
1512 3:20 pm 6:35 pm Apr 18 - May 16
1512 3:20 pm 6:35 pm Apr 11 - Apr 11
3796 5:10 pm 8:25 pm Apr 12 - Apr 26
3796 5:10 pm 8:25 pm May 3 - May 3
4923 5:10 pm 8:25 pm Apr 8 - May 22
1276 8:40 pm 11:55 pm Apr 11 - May 16
1014 9:40 pm 12:55 am Apr 8 - May 22
Airports
Origin

Chicago
$184
Destination

Boston
$184