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

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 Boston Logan International to Chicago Midway

(Round-trip)
Depart: Thu Oct 20 2016 Return: Sat Oct 22 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
MDW
4:55p
BOS
7:05p
2h 10m
nonstop
Depart: Mon Nov 14 2016 Return: Wed Nov 16 2016 Trip spans 3 days
Southwest
Southwest
BOS
12:30a
MDW
3:25a
2h 55m
nonstop
MDW
1:45a
BOS
3:55a
2h 10m
nonstop
Depart: Tue Oct 11 2016 Return: Wed Oct 12 2016 Trip spans 2 days
Delta
Delta
BOS
12:27p
MDW
6:37p
6h 10m
1 stop
MDW
7:06a
BOS
11:59a
4h 53m
1 stop
Depart: Tue Oct 25 2016 Return: Wed Nov 2 2016 Trip spans 9 days
Major Airline
Major Airline
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
MDW
2:00a
BOS
4:10a
2h 10m
nonstop
Depart: Wed Oct 26 2016 Return: Sat Oct 29 2016 Trip spans 4 days
Major Airline
Major Airline
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
MDW
4:55p
BOS
7:05p
2h 10m
nonstop
Depart: Tue Nov 1 2016 Return: Thu Nov 3 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
MDW
2:00a
BOS
4:10a
2h 10m
nonstop
Depart: Wed Nov 2 2016 Return: Fri Nov 4 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
5:20a
MDW
8:05a
2h 45m
nonstop
MDW
5:55p
BOS
8:05p
2h 10m
nonstop
Depart: Sat Oct 29 2016 Return: Sun Oct 30 2016 Trip spans 2 days
Major Airline
Major Airline
BOS
9:45a
MDW
12:35p
2h 50m
nonstop
MDW
2:00a
BOS
4:10a
2h 10m
nonstop
Depart: Thu Oct 27 2016 Return: Sat Oct 29 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
MDW
4:55p
BOS
7:05p
2h 10m
nonstop
Depart: Sat Oct 15 2016 Return: Tue Oct 18 2016 Trip spans 4 days
Delta
Delta
BOS
4:32a
MDW
11:45a
7h 13m
1 stop
MDW
5:18a
BOS
10:52a
5h 34m
1 stop
Depart: Wed Nov 9 2016 Return: Wed Nov 16 2016 Trip spans 8 days
Major Airline
Major Airline
BOS
4:25p
MDW
7:20p
2h 55m
nonstop
MDW
3:30a
BOS
8:30a
5h 00m
nonstop
Depart: Thu Nov 10 2016 Return: Sat Nov 12 2016 Trip spans 3 days
Delta
Delta
BOS
6:30a
MDW
12:57p
6h 27m
1 stop
MDW
7:20a
BOS
11:32a
4h 12m
1 stop
Depart: Wed Oct 12 2016 Return: Mon Nov 21 2016 Trip spans 41 days
Major Airline
Major Airline
BOS
1:35a
MDW
4:20a
2h 45m
nonstop
MDW
4:50p
BOS
7:00p
2h 10m
nonstop
Depart: Sat Nov 12 2016 Return: Mon Nov 14 2016 Trip spans 3 days
Delta
Delta
BOS
11:56a
MDW
4:22p
4h 26m
1 stop
MDW
11:40a
BOS
3:58p
4h 18m
1 stop
Depart: Wed Mar 8 2017 Return: Wed Mar 15 2017 Trip spans 7 days
Major Airline
Major Airline
BOS
6:15a
MDW
9:05a
2h 50m
nonstop
MDW
5:45p
BOS
7:55p
2h 10m
nonstop
Depart: Tue Nov 15 2016 Return: Wed Nov 16 2016 Trip spans 2 days
Delta
Delta
BOS
12:35a
MDW
4:39a
4h 04m
1 stop
MDW
4:14a
BOS
8:02a
3h 48m
1 stop
Depart: Tue Nov 29 2016 Return: Sat Dec 3 2016 Trip spans 5 days
Delta
Delta
BOS
1:00a
MDW
6:33a
5h 33m
1 stop
MDW
12:45a
BOS
4:38a
3h 53m
1 stop
Depart: Sun Oct 30 2016 Return: Wed Nov 2 2016 Trip spans 4 days
Major Airline
Major Airline
BOS
3:00a
MDW
6:50a
3h 50m
nonstop
MDW
1:20p
BOS
3:35p
2h 15m
nonstop
Depart: Sat Dec 3 2016 Return: Sun Dec 4 2016 Trip spans 2 days
Delta
Delta
BOS
9:35a
MDW
5:14p
7h 39m
1 stop
MDW
1:35p
BOS
5:38p
4h 03m
1 stop
Depart: Mon Oct 31 2016 Return: Wed Nov 2 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
3:00a
MDW
6:50a
3h 50m
nonstop
MDW
5:55p
BOS
8:05p
2h 10m
nonstop
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
1543 5:35 am 7:20 am Oct 31 - Oct 31
621 5:35 am 7:20 am Nov 1 - Nov 4
621 5:35 am 7:20 am Oct 3 - Oct 28
3546 6:05 am 7:55 am Oct 2 - Oct 30
3546 6:05 am 7:55 am Oct 29 - Oct 29
3546 6:05 am 7:55 am Oct 22 - Oct 22
3546 6:05 am 7:55 am Oct 8 - Oct 15
3713 8:00 am 9:45 am Oct 8 - Nov 5
267 9:20 am 11:05 am Oct 2 - Oct 31
267 9:20 am 11:05 am Nov 1 - Nov 4
461 11:15 am 1:00 pm Oct 31 - Oct 31
461 11:15 am 1:00 pm Oct 2 - Oct 30
461 11:15 am 1:00 pm Nov 1 - Nov 4
1302 11:50 am 1:40 pm Oct 8 - Oct 29
1295 1:45 pm 3:35 pm Oct 8 - Nov 5
3577 3:45 pm 5:30 pm Oct 8 - Nov 5
1486 3:55 pm 5:40 pm Oct 31 - Oct 31
227 3:55 pm 5:40 pm Nov 1 - Nov 4
227 3:55 pm 5:40 pm Oct 2 - Oct 30
960 8:35 pm 10:20 pm Nov 1 - Nov 4
960 8:35 pm 10:20 pm Oct 2 - Oct 30
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Boston
$104
Destination

Chicago
$104
Airlines Airline reviews

3 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 9.7.

Overall
10.0
Boarding
10.0
Crew
10.0
Comfort
9.3
Food
8.7
Entertainment
10.0