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

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

Book cheap flights from Boston Logan International to Chicago Midway

(Round-trip)
Depart: Wed Jan 14 2015 Return: Sat Jan 17 2015 Trip spans 4 days
Delta
Delta
BOS
7:31a
MDW
1:57p
6h 26m
1 stop
MDW
12:00p
BOS
5:41p
5h 41m
1 stop
Depart: Sat Jan 17 2015 Return: Tue Jan 20 2015 Trip spans 4 days
Delta
Delta
BOS
4:00a
MDW
8:11a
4h 11m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Tue Jan 20 2015 Return: Thu Jan 22 2015 Trip spans 3 days
Delta
Delta
BOS
3:50a
MDW
8:24a
4h 34m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Wed Jan 21 2015 Return: Thu Jan 22 2015 Trip spans 2 days
Delta
Delta
BOS
9:28a
MDW
4:30p
7h 02m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Thu Jan 22 2015 Return: Fri Jan 23 2015 Trip spans 2 days
Delta
Delta
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Fri Jan 23 2015 Return: Sun Jan 25 2015 Trip spans 3 days
Delta
Delta
BOS
11:38a
MDW
4:30p
4h 52m
1 stop
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
Depart: Sat Jan 24 2015 Return: Sun Jan 25 2015 Trip spans 2 days
Delta
Delta
BOS
11:38a
MDW
4:29p
4h 51m
1 stop
MDW
11:31a
BOS
5:34p
6h 03m
1 stop
Depart: Sun Jan 25 2015 Return: Mon Jan 26 2015 Trip spans 2 days
Delta
Delta
BOS
11:38a
MDW
4:30p
4h 52m
1 stop
MDW
12:27p
BOS
5:17p
4h 50m
1 stop
Depart: Mon Jan 26 2015 Return: Tue Jan 27 2015 Trip spans 2 days
Delta
Delta
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
MDW
11:31a
BOS
4:09p
4h 38m
1 stop
Depart: Wed Jan 28 2015 Return: Sat Jan 31 2015 Trip spans 4 days
Delta
Delta
BOS
9:28a
MDW
1:57p
4h 29m
1 stop
MDW
12:00p
BOS
5:28p
5h 28m
1 stop
Depart: Thu Jan 29 2015 Return: Sat Jan 31 2015 Trip spans 3 days
Delta
Delta
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
MDW
12:00p
BOS
5:28p
5h 28m
1 stop
Depart: Fri Jan 30 2015 Return: Sun Feb 1 2015 Trip spans 3 days
Delta
Delta
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
MDW
3:35a
BOS
9:21a
5h 46m
1 stop
Depart: Sat Jan 31 2015 Return: Mon Feb 2 2015 Trip spans 3 days
Delta
Delta
BOS
7:20a
MDW
11:40a
4h 20m
1 stop
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
Depart: Sun Feb 1 2015 Return: Tue Feb 3 2015 Trip spans 3 days
Delta
Delta
BOS
7:31a
MDW
12:04p
4h 33m
1 stop
MDW
11:31a
BOS
4:09p
4h 38m
1 stop
Depart: Mon Feb 2 2015 Return: Sun Feb 8 2015 Trip spans 7 days
Delta
Delta
BOS
5:30a
MDW
11:56a
6h 26m
1 stop
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
Depart: Tue Feb 3 2015 Return: Wed Feb 4 2015 Trip spans 2 days
Delta
Delta
BOS
7:31a
MDW
1:57p
6h 26m
1 stop
MDW
2:00a
BOS
5:56a
3h 56m
1 stop
Depart: Thu Feb 5 2015 Return: Sat Feb 7 2015 Trip spans 3 days
Delta
Delta
BOS
7:31a
MDW
11:56a
4h 25m
1 stop
MDW
7:30a
BOS
11:37a
4h 07m
1 stop
Depart: Fri Feb 6 2015 Return: Sun Feb 8 2015 Trip spans 3 days
Delta
Delta
BOS
6:00a
MDW
1:18p
7h 18m
1 stop
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
Depart: Sun Feb 8 2015 Return: Sun Feb 15 2015 Trip spans 8 days
Delta
Delta
BOS
4:45a
MDW
10:40a
5h 55m
1 stop
MDW
2:05a
BOS
9:24a
7h 19m
1 stop
Depart: Fri Jun 19 2015 Return: Sun Jun 21 2015 Trip spans 3 days
Sun Country Air
Sun Country Air
BOS
7:55a
MDW
5:45p
9h 50m
1 stop
MDW
4:00a
BOS
3:05p
11h 05m
1 stop
Change your search
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
1023 5:50 am 7:50 am Jan 6 - Jan 12
1023 5:50 am 7:50 am Jan 16 - Jan 26
1023 5:50 am 7:50 am Jan 27 - Feb 23
1532 5:55 am 8:00 am Jan 3 - Jan 4
1688 5:55 am 8:00 am Jan 5 - Jan 5
1688 5:55 am 8:00 am Dec 29 - Jan 2
2725 6:35 am 8:30 am Jan 10 - Feb 28
1567 10:40 am 12:40 pm Jan 3 - Jan 3
1567 10:40 am 12:40 pm Jan 4 - Jan 4
200 10:40 am 12:40 pm Jan 1 - Jan 1
4718 10:40 am 12:40 pm Dec 29 - Jan 2
4718 11:05 am 1:05 pm Jan 5 - Jan 5
4199 12:30 pm 2:30 pm Feb 1 - Feb 1
4199 12:30 pm 2:30 pm Jan 11 - Jan 25
3925 12:35 pm 2:35 pm Jan 6 - Mar 6
3792 2:20 pm 4:20 pm Jan 10 - Feb 28
1425 4:05 pm 6:05 pm Jan 6 - Jan 30
61 4:05 pm 6:05 pm Feb 1 - Feb 1
1501 4:35 pm 6:30 pm Jan 3 - Jan 4
433 4:35 pm 6:30 pm Dec 29 - Jan 2
433 4:35 pm 6:30 pm Jan 5 - Jan 5
2991 5:00 pm 6:55 pm Jan 10 - Feb 28
574 7:20 pm 9:15 pm Jan 1 - Jan 1
574 7:20 pm 9:15 pm Jan 4 - Jan 4
3662 7:25 pm 9:20 pm Dec 29 - Jan 5
1399 7:30 pm 9:25 pm Jan 3 - Jan 3
Airports
Origin

Boston
$184
Destination

Chicago
$184