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

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
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 Chicago Midway to Boston Logan International

(Round-trip)
Depart: Sat Jun 3 2017 Return: Wed Jun 7 2017 Trip spans 5 days
Major Airline
Major Airline
MDW
1:00a
BOS
1:42a
0h 42m
nonstop
BOS
9:00a
MDW
11:42a
2h 42m
nonstop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Southwest
Southwest
MDW
4:25p
BOS
6:40p
2h 15m
nonstop
BOS
1:50a
MDW
4:40a
2h 50m
nonstop
Depart: Mon Jun 5 2017 Return: Tue Jun 6 2017 Trip spans 2 days
Delta
Delta
MDW
2:40p
BOS
6:57p
4h 17m
1 stop
BOS
9:55a
MDW
5:00p
7h 05m
1 stop
Depart: Tue Jun 6 2017 Return: Wed Jun 7 2017 Trip spans 2 days
Delta
Delta
MDW
1:52p
BOS
7:59p
6h 07m
1 stop
BOS
8:15a
MDW
2:17p
6h 02m
1 stop
Depart: Mon Jun 19 2017 Return: Tue Jun 20 2017 Trip spans 2 days
Delta
Delta
MDW
1:13p
BOS
7:09p
5h 56m
1 stop
BOS
1:50a
MDW
7:39a
5h 49m
1 stop
Depart: Tue Jun 20 2017 Return: Wed Jun 21 2017 Trip spans 2 days
Delta
Delta
MDW
8:55a
BOS
2:16p
5h 21m
1 stop
BOS
1:50a
MDW
7:39a
5h 49m
1 stop
Depart: Wed Jul 12 2017 Return: Wed Jul 19 2017 Trip spans 8 days
Delta
Delta
MDW
8:10a
BOS
12:58p
4h 48m
1 stop
BOS
1:50a
MDW
7:19a
5h 29m
1 stop
Depart: Thu Aug 3 2017 Return: Sat Aug 5 2017 Trip spans 3 days
Southwest
Southwest
MDW
6:30p
BOS
8:45p
2h 15m
nonstop
BOS
1:55a
MDW
4:45a
2h 50m
nonstop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Delta
Delta
MDW
8:20a
BOS
2:55p
6h 35m
1 stop
BOS
1:15p
MDW
7:48p
6h 33m
1 stop
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Delta
Delta
MDW
8:00a
BOS
1:45p
5h 45m
1 stop
BOS
1:15p
MDW
7:48p
6h 33m
1 stop
Depart: Wed Aug 23 2017 Return: Tue Aug 29 2017 Trip spans 7 days
Delta
Delta
MDW
5:15a
BOS
10:59a
5h 44m
1 stop
BOS
4:30a
MDW
10:37a
6h 07m
1 stop
Depart: Tue Aug 29 2017 Return: Sun Sep 3 2017 Trip spans 6 days
Delta
Delta
MDW
2:00a
BOS
7:45a
5h 45m
1 stop
BOS
5:45a
MDW
2:18p
8h 33m
1 stop
Depart: Wed Aug 30 2017 Return: Sun Sep 3 2017 Trip spans 5 days
Delta
Delta
MDW
2:45p
BOS
6:46p
4h 01m
1 stop
BOS
4:25a
MDW
11:49a
7h 24m
1 stop
Depart: Sat Sep 2 2017 Return: Sun Sep 3 2017 Trip spans 2 days
Delta
Delta
MDW
1:10p
BOS
7:09p
5h 59m
1 stop
BOS
4:25a
MDW
11:49a
7h 24m
1 stop
Depart: Wed Sep 6 2017 Return: Sat Sep 9 2017 Trip spans 4 days
Delta
Delta
MDW
5:15a
BOS
10:59a
5h 44m
1 stop
BOS
1:45a
MDW
5:48a
4h 03m
1 stop
Depart: Sat Sep 9 2017 Return: Tue Sep 12 2017 Trip spans 4 days
Delta
Delta
MDW
1:10p
BOS
7:09p
5h 59m
1 stop
BOS
5:00a
MDW
9:34a
4h 34m
1 stop
Depart: Sat Sep 23 2017 Return: Sat Sep 30 2017 Trip spans 8 days
Delta
Delta
MDW
11:24a
BOS
7:09p
7h 45m
1 stop
BOS
1:45a
MDW
6:18a
4h 33m
1 stop
Depart: Mon Sep 25 2017 Return: Wed Sep 27 2017 Trip spans 3 days
Delta
Delta
MDW
5:15a
BOS
10:59a
5h 44m
1 stop
BOS
5:00a
MDW
9:34a
4h 34m
1 stop
Depart: Tue Sep 26 2017 Return: Sat Sep 30 2017 Trip spans 5 days
Delta
Delta
MDW
8:20a
BOS
2:55p
6h 35m
1 stop
BOS
1:45a
MDW
6:18a
4h 33m
1 stop
Depart: Wed Sep 27 2017 Return: Sat Sep 30 2017 Trip spans 4 days
Delta
Delta
MDW
3:00a
BOS
6:54a
3h 54m
1 stop
BOS
1:45a
MDW
6:18a
4h 33m
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
1707 5:25 am 8:35 am Jun 5 - Jun 30
5407 5:40 am 8:55 am Jul 3 - Jul 3
2657 6:00 am 9:15 am Jun 10 - Aug 12
2581 7:05 am 10:20 am May 20 - Jun 3
429 7:15 am 10:35 am May 22 - Jun 2
107 7:30 am 10:45 am Jun 5 - Jun 30
3239 7:30 am 10:45 am Jun 4 - Aug 13
107 7:35 am 10:50 am Jul 3 - Jul 3
153 7:45 am 11:00 am Jun 10 - Aug 12
5224 9:05 am 12:25 pm Jun 4 - Aug 13
4450 10:05 am 1:20 pm May 20 - Jun 3
3318 10:40 am 1:55 pm Jun 4 - Aug 13
1812 11:25 am 2:40 pm Jun 5 - Jun 30
1812 11:25 am 2:40 pm Jul 3 - Jul 3
2397 12:25 pm 3:40 pm Jun 4 - Aug 13
1587 1:45 pm 5:05 pm May 30 - Jun 2
5023 1:50 pm 5:10 pm May 20 - Jun 3
1908 2:05 pm 5:25 pm Jun 18 - Aug 13
1908 2:05 pm 5:25 pm Jun 4 - Jun 11
3431 2:20 pm 5:40 pm Jun 5 - Jun 30
4455 2:20 pm 5:40 pm Jul 3 - Jul 3
1426 2:55 pm 6:15 pm Jun 10 - Aug 12
346 6:30 pm 9:45 pm Jun 5 - Jun 30
220 6:50 pm 10:05 pm May 30 - Jun 2
4373 7:00 pm 10:15 pm Jun 10 - Aug 12
6574 7:15 pm 10:30 pm Jul 3 - Jul 3
5885 8:50 pm 12:05 am Jun 10 - Aug 12
4393 9:05 pm 12:20 am Jun 3 - Jun 3
595 9:50 pm 1:05 am May 22 - Jun 2
2089 10:15 pm 1:30 am Jun 4 - Aug 13
1592 10:30 pm 1:45 am Jun 5 - Jun 30
4663 10:35 pm 1:50 am Jun 10 - Aug 12
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
$167
Destination

Boston
$167
Airlines Airline reviews

12 travelers who booked a flight from Chicago to Boston rated their chosen airlines with an average of 8.8.

Overall
8.7
Boarding
9.0
Crew
9.2
Comfort
9.0
Food
8.2
Entertainment
7.8