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
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: Wed Oct 5 2016 Return: Wed Nov 9 2016 Trip spans 36 days
Major Airline
Major Airline
MDW
2:00a
BOS
4:10a
2h 10m
nonstop
BOS
4:25p
MDW
7:20p
2h 55m
nonstop
Depart: Thu Nov 10 2016 Return: Wed Nov 16 2016 Trip spans 7 days
Southwest
Southwest
MDW
3:30a
BOS
8:30a
5h 00m
1 stop
BOS
3:00a
MDW
7:05a
4h 05m
1 stop
Depart: Sat Oct 8 2016 Return: Tue Oct 11 2016 Trip spans 4 days
Delta
Delta
MDW
1:24p
BOS
6:48p
5h 24m
1 stop
BOS
2:50a
MDW
9:26a
6h 36m
1 stop
Depart: Wed Oct 19 2016 Return: Wed Oct 26 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
5:55p
BOS
8:05p
2h 10m
nonstop
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
Depart: Sat Oct 22 2016 Return: Sun Oct 30 2016 Trip spans 9 days
Major Airline
Major Airline
MDW
4:55p
BOS
7:05p
2h 10m
nonstop
BOS
2:05a
MDW
4:55a
2h 50m
nonstop
Depart: Tue Oct 25 2016 Return: Tue Nov 1 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
2:00a
BOS
4:10a
2h 10m
nonstop
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
Depart: Wed Oct 26 2016 Return: Thu Oct 27 2016 Trip spans 2 days
Major Airline
Major Airline
MDW
5:55p
BOS
8:05p
2h 10m
nonstop
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
Depart: Fri Oct 28 2016 Return: Tue Nov 1 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
5:55p
BOS
8:05p
2h 10m
nonstop
BOS
4:35p
MDW
7:20p
2h 45m
nonstop
Depart: Sat Oct 29 2016 Return: Tue Nov 1 2016 Trip spans 4 days
Major Airline
Major Airline
MDW
4:55p
BOS
7:05p
2h 10m
nonstop
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
Depart: Sun Oct 30 2016 Return: Tue Nov 1 2016 Trip spans 3 days
Major Airline
Major Airline
MDW
2:00a
BOS
4:10a
2h 10m
nonstop
BOS
4:35p
MDW
7:20p
2h 45m
nonstop
Depart: Tue Jan 3 2017 Return: Wed Jan 11 2017 Trip spans 9 days
Major Airline
Major Airline
MDW
4:50p
BOS
7:00p
2h 10m
nonstop
BOS
12:50a
MDW
3:45a
2h 55m
nonstop
Depart: Tue Oct 11 2016 Return: Wed Oct 12 2016 Trip spans 2 days
Delta
Delta
MDW
1:24p
BOS
6:51p
5h 27m
1 stop
BOS
4:45a
MDW
9:26a
4h 41m
1 stop
Depart: Mon Oct 24 2016 Return: Tue Oct 25 2016 Trip spans 2 days
Delta
Delta
MDW
3:00a
BOS
8:58a
5h 58m
1 stop
BOS
8:33a
MDW
12:57p
4h 24m
1 stop
Depart: Tue Nov 29 2016 Return: Tue Dec 6 2016 Trip spans 8 days
Major Airline
Major Airline
MDW
1:30p
BOS
5:35p
4h 05m
nonstop
BOS
10:05a
MDW
2:25p
4h 20m
nonstop
Depart: Tue Nov 1 2016 Return: Wed Nov 2 2016 Trip spans 2 days
Delta
Delta
MDW
2:00a
BOS
8:45a
6h 45m
1 stop
BOS
1:35a
MDW
5:43a
4h 08m
1 stop
Depart: Tue Dec 6 2016 Return: Wed Dec 7 2016 Trip spans 2 days
Major Airline
Major Airline
MDW
3:30a
BOS
8:30a
5h 00m
nonstop
BOS
3:00a
MDW
7:05a
4h 05m
nonstop
Depart: Mon Nov 7 2016 Return: Tue Nov 8 2016 Trip spans 2 days
Delta
Delta
MDW
2:00a
BOS
5:51a
3h 51m
1 stop
BOS
12:34a
MDW
4:40a
4h 06m
1 stop
Depart: Mon Oct 17 2016 Return: Thu Oct 20 2016 Trip spans 4 days
Major Airline
Major Airline
MDW
5:55p
BOS
8:05p
2h 10m
nonstop
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
Depart: Wed Nov 9 2016 Return: Sun Nov 13 2016 Trip spans 5 days
Delta
Delta
MDW
7:20a
BOS
11:33a
4h 13m
1 stop
BOS
1:00a
MDW
7:45a
6h 45m
1 stop
Depart: Fri Nov 18 2016 Return: Sat Nov 19 2016 Trip spans 2 days
Delta
Delta
MDW
1:30a
BOS
7:49a
6h 19m
1 stop
BOS
3:00a
MDW
10:54a
7h 54m
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
493 6:00 am 9:10 am Oct 2 - Nov 4
1118 6:20 am 9:40 am Oct 8 - Nov 5
1260 11:30 am 2:45 pm Oct 2 - Oct 28
1260 11:30 am 2:45 pm Nov 1 - Nov 4
1657 11:30 am 2:45 pm Oct 30 - Oct 30
1657 11:30 am 2:45 pm Oct 31 - Oct 31
918 11:30 am 2:45 pm Oct 8 - Nov 5
2288 1:40 pm 5:00 pm Oct 2 - Nov 4
3705 1:55 pm 5:15 pm Oct 8 - Nov 5
678 5:20 pm 8:35 pm Oct 2 - Oct 30
678 5:20 pm 8:35 pm Nov 1 - Nov 4
2614 5:30 pm 8:45 pm Oct 8 - Nov 5
2523 7:10 pm 10:20 pm Oct 31 - Oct 31
3668 8:55 pm 12:05 am Nov 5 - Nov 5
3668 8:55 pm 12:05 am Sep 24 - Oct 29
484 9:55 pm 1:05 am Nov 1 - Nov 4
484 9:55 pm 1:05 am Oct 30 - Oct 30
484 9:55 pm 1:05 am Oct 23 - Oct 28
484 9:55 pm 1:05 am Oct 2 - Oct 21
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
$104
Destination

Boston
$104
Airlines Airline reviews

5 travelers who booked a flight from Chicago to Boston rated their chosen airlines with an average of 8.2.

Overall
7.6
Boarding
8.4
Crew
8.8
Comfort
8.8
Food
8.0
Entertainment
7.6