Find Deals on 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
Students
under 26
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: Thu Jan 19 2017 Return: Sun Jan 22 2017 Trip spans 4 days
Southwest
Southwest
MDW
2:25a
BOS
4:40a
2h 15m
nonstop
BOS
1:20a
MDW
4:15a
2h 55m
nonstop
Depart: Fri Dec 9 2016 Return: Mon Dec 12 2016 Trip spans 4 days
Delta
Delta
MDW
4:19a
BOS
9:39a
5h 20m
1 stop
BOS
9:30a
MDW
3:09p
5h 39m
1 stop
Depart: Sun Dec 11 2016 Return: Wed Dec 14 2016 Trip spans 4 days
Southwest
Southwest
MDW
4:50p
BOS
7:00p
2h 10m
nonstop
BOS
11:25a
MDW
2:20p
2h 55m
nonstop
Depart: Sat Dec 10 2016 Return: Sun Dec 11 2016 Trip spans 2 days
Delta
Delta
MDW
10:20a
BOS
3:28p
5h 08m
1 stop
BOS
6:00a
MDW
12:01p
6h 01m
1 stop
Depart: Mon Dec 12 2016 Return: Wed Dec 14 2016 Trip spans 3 days
Delta
Delta
MDW
11:40a
BOS
3:48p
4h 08m
1 stop
BOS
11:55a
MDW
4:40p
4h 45m
1 stop
Depart: Tue Dec 20 2016 Return: Tue Jan 31 2017 Trip spans 43 days
Delta
Delta
MDW
7:47a
BOS
12:02p
4h 15m
1 stop
BOS
11:36a
MDW
6:09p
6h 33m
1 stop
Depart: Sat Dec 24 2016 Return: Thu Jan 5 2017 Trip spans 13 days
Delta
Delta
MDW
10:16a
BOS
5:54p
7h 38m
1 stop
BOS
3:40a
MDW
8:22a
4h 42m
1 stop
Depart: Wed Jan 4 2017 Return: Fri Jan 6 2017 Trip spans 3 days
Delta
Delta
MDW
12:22p
BOS
5:53p
5h 31m
1 stop
BOS
1:50a
MDW
8:22a
6h 32m
1 stop
Depart: Thu Jan 5 2017 Return: Sat Jan 7 2017 Trip spans 3 days
Delta
Delta
MDW
5:58a
BOS
11:08a
5h 10m
1 stop
BOS
1:00a
MDW
6:57a
5h 57m
1 stop
Depart: Sat Jan 7 2017 Return: Sun Jan 8 2017 Trip spans 2 days
Delta
Delta
MDW
12:11p
BOS
5:56p
5h 45m
1 stop
BOS
12:34a
MDW
5:12a
4h 38m
1 stop
Depart: Wed Jan 11 2017 Return: Sun Jan 15 2017 Trip spans 5 days
Delta
Delta
MDW
4:15a
BOS
7:59a
3h 44m
1 stop
BOS
1:55a
MDW
8:34a
6h 39m
1 stop
Depart: Fri Jan 13 2017 Return: Mon Jan 16 2017 Trip spans 4 days
Delta
Delta
MDW
7:35a
BOS
1:46p
6h 11m
1 stop
BOS
6:55a
MDW
12:51p
5h 56m
1 stop
Depart: Sat Jan 14 2017 Return: Tue Jan 17 2017 Trip spans 4 days
Delta
Delta
MDW
12:11p
BOS
5:56p
5h 45m
1 stop
BOS
11:36a
MDW
6:09p
6h 33m
1 stop
Depart: Tue Jan 17 2017 Return: Wed Jan 18 2017 Trip spans 2 days
Delta
Delta
MDW
1:45a
BOS
5:58a
4h 13m
1 stop
BOS
7:33a
MDW
12:11p
4h 38m
1 stop
Depart: Wed Jan 18 2017 Return: Thu Jan 19 2017 Trip spans 2 days
Delta
Delta
MDW
4:15a
BOS
7:59a
3h 44m
1 stop
BOS
6:55a
MDW
12:51p
5h 56m
1 stop
Depart: Fri Jan 20 2017 Return: Sun Jan 29 2017 Trip spans 10 days
Delta
Delta
MDW
10:29a
BOS
3:58p
5h 29m
1 stop
BOS
12:34a
MDW
5:12a
4h 38m
1 stop
Depart: Sat Jan 21 2017 Return: Tue Jan 24 2017 Trip spans 4 days
Delta
Delta
MDW
7:15a
BOS
11:53a
4h 38m
1 stop
BOS
11:58a
MDW
5:00p
5h 02m
1 stop
Depart: Fri Jan 27 2017 Return: Tue Jan 31 2017 Trip spans 5 days
Delta
Delta
MDW
1:40p
BOS
5:56p
4h 16m
1 stop
BOS
11:58a
MDW
5:00p
5h 02m
1 stop
Depart: Sat Jan 28 2017 Return: Sun Jan 29 2017 Trip spans 2 days
Delta
Delta
MDW
7:15a
BOS
11:53a
4h 38m
1 stop
BOS
12:34a
MDW
5:12a
4h 38m
1 stop
Depart: Wed Feb 1 2017 Return: Sat Feb 4 2017 Trip spans 4 days
Delta
Delta
MDW
7:35a
BOS
11:56a
4h 21m
1 stop
BOS
7:31a
MDW
12:09p
4h 38m
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
6255 5:20 am 8:25 am Dec 21 - Jan 2
1322 6:30 am 9:40 am Dec 17 - Dec 17
686 6:45 am 9:55 am Nov 29 - Dec 20
686 6:45 am 9:55 am Jan 3 - Jan 4
532 7:05 am 10:20 am Jan 5 - Jan 13
1893 8:15 am 11:25 am Dec 24 - Dec 24
5452 8:15 am 11:25 am Dec 3 - Dec 10
6662 8:15 am 11:25 am Dec 31 - Dec 31
4040 11:30 am 2:35 pm Dec 21 - Jan 2
5152 11:30 am 2:45 pm Jan 7 - Mar 4
1429 1:15 pm 4:25 pm Dec 17 - Dec 17
934 1:20 pm 4:35 pm Jan 5 - Jan 13
2447 1:35 pm 4:45 pm Nov 29 - Dec 20
2447 1:35 pm 4:45 pm Jan 1 - Jan 4
3305 1:35 pm 4:45 pm Dec 25 - Dec 25
4925 2:00 pm 5:10 pm Dec 21 - Jan 2
4348 2:25 pm 5:40 pm Jan 8 - Jan 29
5444 2:30 pm 5:45 pm Jan 7 - Mar 4
1803 2:35 pm 5:45 pm Dec 31 - Dec 31
3852 2:35 pm 5:45 pm Dec 3 - Dec 10
409 2:35 pm 5:45 pm Dec 24 - Dec 24
1573 5:40 pm 8:50 pm Dec 25 - Dec 25
2511 5:40 pm 8:50 pm Nov 30 - Dec 14
2511 5:40 pm 8:50 pm Jan 4 - Jan 4
2511 5:40 pm 8:50 pm Jan 1 - Jan 3
2511 5:40 pm 8:50 pm Dec 18 - Dec 20
2511 5:40 pm 8:50 pm Dec 11 - Dec 16
3562 5:45 pm 8:55 pm Dec 21 - Jan 2
1261 6:05 pm 9:15 pm Dec 17 - Dec 17
3622 7:15 pm 10:25 pm Jan 8 - Jan 29
6381 7:45 pm 11:00 pm Dec 21 - Jan 2
2037 8:55 pm 12:05 am Jan 7 - Mar 4
1369 9:05 pm 12:15 am Dec 3 - Dec 10
6427 9:05 pm 12:15 am Dec 31 - Dec 31
2080 9:10 pm 12:20 am Dec 17 - Dec 17
4309 9:10 pm 12:20 am Jan 8 - Jan 29
5818 9:15 pm 12:25 am Dec 21 - Jan 2
4211 9:45 pm 1:00 am Jan 5 - Feb 13
2993 9:50 pm 1:00 am Jan 1 - Jan 3
2993 9:50 pm 1:00 am Nov 29 - Dec 20
3522 9:50 pm 1:00 am Dec 25 - Dec 25
4199 10:45 pm 1:55 am Dec 21 - Jan 2
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
$162
Destination

Boston
$162
Airlines Airline reviews

7 travelers who booked a flight from Chicago to Boston rated their chosen airlines with an average of 8.4.

Overall
8.0
Boarding
8.6
Crew
8.9
Comfort
8.9
Food
8.3
Entertainment
8.0