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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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 Sep 16 2015 Return: Mon Sep 21 2015 Trip spans 6 days
Delta
Delta
MDW
5:17a
BOS
10:54a
5h 37m
1 stop
BOS
9:30a
MDW
3:40p
6h 10m
1 stop
Depart: Sat Sep 19 2015 Return: Mon Sep 21 2015 Trip spans 3 days
Delta
Delta
MDW
8:15a
BOS
12:37p
4h 22m
1 stop
BOS
9:30a
MDW
3:40p
6h 10m
1 stop
Depart: Mon Sep 21 2015 Return: Thu Sep 24 2015 Trip spans 4 days
Delta
Delta
MDW
2:35p
BOS
6:43p
4h 08m
1 stop
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
Depart: Tue Sep 22 2015 Return: Wed Sep 30 2015 Trip spans 9 days
Delta
Delta
MDW
5:17a
BOS
9:02a
3h 45m
1 stop
BOS
10:42a
MDW
2:54p
4h 12m
1 stop
Depart: Wed Sep 23 2015 Return: Wed Sep 30 2015 Trip spans 8 days
Delta
Delta
MDW
5:17a
BOS
9:02a
3h 45m
1 stop
BOS
8:34a
MDW
12:59p
4h 25m
1 stop
Depart: Sat Sep 26 2015 Return: Thu Oct 1 2015 Trip spans 6 days
Delta
Delta
MDW
11:11a
BOS
6:25p
7h 14m
1 stop
BOS
1:45a
MDW
5:43a
3h 58m
1 stop
Depart: Mon Sep 28 2015 Return: Sat Oct 3 2015 Trip spans 6 days
Delta
Delta
MDW
12:35p
BOS
6:43p
6h 08m
1 stop
BOS
1:40a
MDW
5:43a
4h 03m
1 stop
Depart: Tue Sep 29 2015 Return: Fri Oct 2 2015 Trip spans 4 days
Delta
Delta
MDW
3:00a
BOS
6:54a
3h 54m
1 stop
BOS
2:05a
MDW
7:31a
5h 26m
1 stop
Depart: Wed Sep 30 2015 Return: Tue Oct 6 2015 Trip spans 7 days
Delta
Delta
MDW
8:39a
BOS
12:20p
3h 41m
1 stop
BOS
5:15a
MDW
9:15a
4h 00m
1 stop
Depart: Mon Oct 5 2015 Return: Tue Oct 6 2015 Trip spans 2 days
Delta
Delta
MDW
2:35p
BOS
6:44p
4h 09m
1 stop
BOS
5:15a
MDW
9:15a
4h 00m
1 stop
Depart: Tue Oct 6 2015 Return: Thu Oct 15 2015 Trip spans 10 days
Delta
Delta
MDW
8:38a
BOS
12:21p
3h 43m
1 stop
BOS
1:45a
MDW
5:43a
3h 58m
1 stop
Depart: Wed Oct 7 2015 Return: Thu Oct 15 2015 Trip spans 9 days
Delta
Delta
MDW
8:38a
BOS
12:21p
3h 43m
1 stop
BOS
1:45a
MDW
5:43a
3h 58m
1 stop
Depart: Tue Oct 13 2015 Return: Thu Oct 22 2015 Trip spans 10 days
Delta
Delta
MDW
2:35p
BOS
6:44p
4h 09m
1 stop
BOS
1:45a
MDW
5:43a
3h 58m
1 stop
Depart: Wed Oct 14 2015 Return: Thu Oct 22 2015 Trip spans 9 days
Delta
Delta
MDW
8:38a
BOS
12:21p
3h 43m
1 stop
BOS
5:15a
MDW
9:15a
4h 00m
1 stop
Depart: Sat Oct 24 2015 Return: Sat Oct 31 2015 Trip spans 8 days
Delta
Delta
MDW
11:20a
BOS
7:27p
8h 07m
1 stop
BOS
8:15a
MDW
12:51p
4h 36m
1 stop
Depart: Mon Oct 26 2015 Return: Thu Oct 29 2015 Trip spans 4 days
Delta
Delta
MDW
5:18a
BOS
10:39a
5h 21m
1 stop
BOS
5:15a
MDW
9:15a
4h 00m
1 stop
Depart: Tue Oct 27 2015 Return: Sat Oct 31 2015 Trip spans 5 days
Delta
Delta
MDW
1:45a
BOS
5:35a
3h 50m
1 stop
BOS
1:40a
MDW
5:43a
4h 03m
1 stop
Depart: Wed Oct 28 2015 Return: Fri Oct 30 2015 Trip spans 3 days
Delta
Delta
MDW
1:45a
BOS
5:35a
3h 50m
1 stop
BOS
1:45a
MDW
5:43a
3h 58m
1 stop
Depart: Mon Nov 2 2015 Return: Tue Nov 3 2015 Trip spans 2 days
Delta
Delta
MDW
7:31a
BOS
11:49a
4h 18m
1 stop
BOS
7:33a
MDW
11:53a
4h 20m
1 stop
Depart: Tue Nov 3 2015 Return: Wed Nov 4 2015 Trip spans 2 days
Delta
Delta
MDW
7:31a
BOS
11:49a
4h 18m
1 stop
BOS
7:33a
MDW
11:53a
4h 20m
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
2784 5:30 am 8:40 am Sep 1 - Sep 11
2784 5:30 am 8:40 am Sep 13 - Oct 30
3152 6:45 am 9:55 am Sep 12 - Oct 31
595 7:55 am 11:05 am Sep 1 - Sep 10
1084 8:10 am 11:20 am Sep 27 - Oct 25
3921 8:55 am 12:05 pm Sep 13 - Sep 20
3921 8:55 am 12:05 pm Sep 28 - Oct 23
3923 8:55 am 12:05 pm Sep 11 - Sep 25
4485 10:50 am 2:05 pm Oct 3 - Oct 31
4485 10:50 am 2:05 pm Sep 12 - Sep 26
1029 1:30 pm 4:50 pm Sep 27 - Oct 25
3041 1:30 pm 4:50 pm Sep 7 - Sep 10
3041 1:30 pm 4:50 pm Sep 28 - Oct 30
3041 1:30 pm 4:50 pm Sep 11 - Sep 25
4532 1:30 pm 4:50 pm Oct 3 - Oct 31
4532 1:30 pm 4:50 pm Sep 12 - Sep 26
1944 5:05 pm 8:20 pm Sep 27 - Oct 25
286 5:05 pm 8:20 pm Oct 5 - Oct 9
286 5:05 pm 8:20 pm Sep 28 - Oct 2
286 5:05 pm 8:20 pm Sep 22 - Sep 25
286 5:05 pm 8:20 pm Sep 13 - Sep 20
286 5:05 pm 8:20 pm Sep 11 - Sep 21
286 5:05 pm 8:20 pm Sep 8 - Sep 10
3501 5:45 pm 9:00 pm Sep 12 - Oct 24
728 8:40 pm 11:55 pm Sep 12 - Sep 26
4514 8:50 pm 12:05 am Oct 3 - Oct 24
2269 9:40 pm 12:55 am Sep 6 - Sep 10
2269 9:45 pm 1:00 am Oct 11 - Oct 21
2269 9:45 pm 12:55 am Sep 11 - Sep 25
2269 9:45 pm 1:00 am Oct 4 - Oct 9
2269 9:45 pm 1:00 am Sep 27 - Oct 2
Airports
Origin

Chicago
$184
Destination

Boston
$184
Airlines