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

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.
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Book cheap flights from Boston Logan International to Chicago Midway

(Round-trip)
Depart: Thu Sep 3 2015 Return: Sat Sep 12 2015 Trip spans 10 days
Delta
Delta
BOS
2:20a
MDW
7:36a
5h 16m
1 stop
MDW
2:35a
BOS
8:44a
6h 09m
1 stop
Depart: Tue Sep 8 2015 Return: Wed Sep 16 2015 Trip spans 9 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
3:05a
BOS
8:55a
5h 50m
1 stop
Depart: Thu Sep 24 2015 Return: Mon Sep 28 2015 Trip spans 5 days
Delta
Delta
BOS
3:00a
MDW
9:23a
6h 23m
1 stop
MDW
5:17a
BOS
10:54a
5h 37m
1 stop
Depart: Sat Oct 24 2015 Return: Mon Oct 26 2015 Trip spans 3 days
Delta
Delta
BOS
1:45a
MDW
5:48a
4h 03m
1 stop
MDW
8:36a
BOS
12:21p
3h 45m
1 stop
Depart: Wed Nov 4 2015 Return: Fri Nov 6 2015 Trip spans 3 days
Delta
Delta
BOS
9:43a
MDW
1:50p
4h 07m
1 stop
MDW
2:00a
BOS
6:00a
4h 00m
1 stop
Depart: Sat Nov 7 2015 Return: Mon Nov 9 2015 Trip spans 3 days
Delta
Delta
BOS
7:30a
MDW
12:10p
4h 40m
1 stop
MDW
11:45a
BOS
5:32p
5h 47m
1 stop
Depart: Wed Nov 11 2015 Return: Sat Nov 14 2015 Trip spans 4 days
Delta
Delta
BOS
4:15a
MDW
8:15a
4h 00m
1 stop
MDW
7:40a
BOS
11:30a
3h 50m
1 stop
Depart: Thu Nov 12 2015 Return: Sat Nov 14 2015 Trip spans 3 days
Delta
Delta
BOS
4:15a
MDW
8:15a
4h 00m
1 stop
MDW
7:40a
BOS
11:30a
3h 50m
1 stop
Depart: Sat Nov 14 2015 Return: Tue Nov 17 2015 Trip spans 4 days
Delta
Delta
BOS
7:30a
MDW
12:10p
4h 40m
1 stop
MDW
1:30p
BOS
5:32p
4h 02m
1 stop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 days
Delta
Delta
BOS
3:10a
MDW
9:23a
6h 13m
1 stop
MDW
5:00a
BOS
10:53a
5h 53m
1 stop
Depart: Tue Aug 25 2015 Return: Wed Aug 26 2015 Trip spans 2 days
Delta
Delta
BOS
10:40a
MDW
2:55p
4h 15m
1 stop
MDW
8:31a
BOS
12:20p
3h 49m
1 stop
Depart: Wed Aug 26 2015 Return: Tue Sep 1 2015 Trip spans 7 days
Delta
Delta
BOS
3:10a
MDW
9:23a
6h 13m
1 stop
MDW
2:00a
BOS
7:40a
5h 40m
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
3:00a
BOS
6:54a
3h 54m
1 stop
Depart: Sun Aug 30 2015 Return: Wed Sep 2 2015 Trip spans 4 days
Delta
Delta
BOS
2:14a
MDW
7:25a
5h 11m
1 stop
MDW
5:17a
BOS
9:02a
3h 45m
1 stop
Depart: Mon Aug 31 2015 Return: Tue Sep 1 2015 Trip spans 2 days
Delta
Delta
BOS
7:05a
MDW
12:58p
5h 53m
1 stop
MDW
3:00a
BOS
6:54a
3h 54m
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: Sun Sep 6 2015 Return: Wed Sep 9 2015 Trip spans 4 days
Delta
Delta
BOS
7:24a
MDW
1:39p
6h 15m
1 stop
MDW
8:25a
BOS
2:04p
5h 39m
1 stop
Depart: Wed Sep 9 2015 Return: Sat Sep 12 2015 Trip spans 4 days
Delta
Delta
BOS
8:34a
MDW
12:58p
4h 24m
1 stop
MDW
12:35p
BOS
4:59p
4h 24m
1 stop
Depart: Fri Sep 11 2015 Return: Sat Sep 12 2015 Trip spans 2 days
Delta
Delta
BOS
5:16a
MDW
9:23a
4h 07m
1 stop
MDW
12:35p
BOS
4:59p
4h 24m
1 stop
Depart: Sun Aug 23 2015 Return: Fri Aug 28 2015 Trip spans 6 days
Southwest
Southwest
BOS
1:30a
MDW
4:20a
2h 50m
nonstop
MDW
11:40a
BOS
4:05p
4h 25m
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 Aug 1 - Aug 8
527 5:30 am 7:10 am Jul 28 - Aug 7
6526 5:30 am 7:20 am Aug 10 - Sep 4
3114 6:25 am 8:15 am Aug 15 - Aug 29
5185 6:25 am 8:15 am Sep 5 - Sep 5
2117 8:00 am 9:50 am Aug 15 - Aug 29
665 8:25 am 10:05 am Jul 28 - Aug 7
1755 8:30 am 10:10 am Aug 1 - Aug 8
669 9:15 am 11:00 am Aug 9 - Sep 6
5139 9:45 am 11:30 am Sep 5 - Sep 5
804 9:45 am 11:30 am Aug 15 - Aug 29
1025 11:55 am 1:40 pm Aug 9 - Sep 4
4903 11:55 am 1:40 pm Aug 15 - Aug 29
6714 11:55 am 1:40 pm Sep 5 - Sep 5
438 12:50 pm 2:25 pm Jul 28 - Aug 7
2 1:35 pm 3:10 pm Aug 1 - Aug 8
4535 3:40 pm 5:25 pm Aug 8 - Aug 8
1426 4:00 pm 5:45 pm Aug 15 - Aug 29
6025 4:00 pm 5:45 pm Sep 5 - Sep 5
514 4:30 pm 6:20 pm Aug 9 - Sep 4
383 5:00 pm 6:50 pm Jul 28 - Aug 7
4429 8:35 pm 10:20 pm Jul 28 - Aug 7
5474 8:40 pm 10:25 pm Aug 8 - Aug 8
2581 8:55 pm 10:40 pm Aug 9 - Sep 4
1476 9:40 pm 11:25 pm Aug 1 - Aug 8
413 9:55 pm 11:35 pm Jul 28 - Aug 7
Airports
Origin

Boston
$164
Destination

Chicago
$164