Find Cheap 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: Tue Nov 7 2017 Return: Thu Nov 9 2017 Trip spans 3 days
Southwest
Southwest
BOS
12:05a
MDW
2:55a
2h 50m
nonstop
MDW
5:30p
BOS
7:45p
2h 15m
nonstop
Depart: Sat Jun 3 2017 Return: Mon Jun 5 2017 Trip spans 3 days
Delta
Delta
BOS
12:00p
MDW
7:19p
7h 19m
1 stop
MDW
2:40p
BOS
6:57p
4h 17m
1 stop
Depart: Tue Jun 6 2017 Return: Wed Jun 7 2017 Trip spans 2 days
Delta
Delta
BOS
9:55a
MDW
3:45p
5h 50m
1 stop
MDW
2:40p
BOS
7:02p
4h 22m
1 stop
Depart: Wed Jun 7 2017 Return: Mon Jun 12 2017 Trip spans 6 days
Delta
Delta
BOS
4:50a
MDW
9:23a
4h 33m
1 stop
MDW
2:50p
BOS
6:42p
3h 52m
1 stop
Depart: Tue Jun 13 2017 Return: Mon Jun 19 2017 Trip spans 7 days
Delta
Delta
BOS
1:50a
MDW
7:39a
5h 49m
1 stop
MDW
1:59p
BOS
7:59p
6h 00m
1 stop
Depart: Mon Jul 24 2017 Return: Tue Sep 12 2017 Trip spans 51 days
Southwest
Southwest
BOS
1:50a
MDW
4:25a
2h 35m
nonstop
MDW
6:40p
BOS
8:55p
2h 15m
nonstop
Depart: Wed Jun 14 2017 Return: Mon Jun 19 2017 Trip spans 6 days
Delta
Delta
BOS
1:50a
MDW
7:39a
5h 49m
1 stop
MDW
1:59p
BOS
7:59p
6h 00m
1 stop
Depart: Sat Nov 4 2017 Return: Sat Nov 11 2017 Trip spans 8 days
Southwest
Southwest
BOS
1:50a
MDW
4:30a
2h 40m
nonstop
MDW
4:15p
BOS
6:25p
2h 10m
nonstop
Depart: Fri Jun 16 2017 Return: Mon Jun 19 2017 Trip spans 4 days
Delta
Delta
BOS
1:40a
MDW
5:46a
4h 06m
1 stop
MDW
1:59p
BOS
7:59p
6h 00m
1 stop
Depart: Wed Jul 19 2017 Return: Tue Jul 25 2017 Trip spans 7 days
Delta
Delta
BOS
1:50a
MDW
7:19a
5h 29m
1 stop
MDW
5:18a
BOS
10:47a
5h 29m
1 stop
Depart: Wed Aug 2 2017 Return: Sun Aug 13 2017 Trip spans 12 days
Southwest
Southwest
BOS
1:50a
MDW
4:25a
2h 35m
nonstop
MDW
6:15p
BOS
8:30p
2h 15m
nonstop
Depart: Tue Jul 25 2017 Return: Tue Aug 8 2017 Trip spans 15 days
Delta
Delta
BOS
1:50a
MDW
7:19a
5h 29m
1 stop
MDW
8:00a
BOS
2:04p
6h 04m
1 stop
Depart: Wed Aug 23 2017 Return: Wed Aug 30 2017 Trip spans 8 days
Delta
Delta
BOS
10:35a
MDW
3:08p
4h 33m
1 stop
MDW
5:15a
BOS
10:59a
5h 44m
1 stop
Depart: Tue Aug 29 2017 Return: Sat Sep 2 2017 Trip spans 5 days
Delta
Delta
BOS
10:45a
MDW
6:07p
7h 22m
1 stop
MDW
1:10p
BOS
7:09p
5h 59m
1 stop
Depart: Wed Aug 30 2017 Return: Sat Sep 2 2017 Trip spans 4 days
Delta
Delta
BOS
1:45a
MDW
5:50a
4h 05m
1 stop
MDW
1:10p
BOS
7:09p
5h 59m
1 stop
Depart: Thu Aug 31 2017 Return: Sat Sep 2 2017 Trip spans 3 days
Delta
Delta
BOS
2:00a
MDW
8:40a
6h 40m
1 stop
MDW
1:10p
BOS
7:09p
5h 59m
1 stop
Depart: Sun Sep 3 2017 Return: Sat Sep 9 2017 Trip spans 7 days
Delta
Delta
BOS
5:45a
MDW
2:18p
8h 33m
1 stop
MDW
12:15p
BOS
6:40p
6h 25m
1 stop
Depart: Wed Sep 6 2017 Return: Sat Sep 9 2017 Trip spans 4 days
Delta
Delta
BOS
8:35a
MDW
12:59p
4h 24m
1 stop
MDW
12:15p
BOS
6:40p
6h 25m
1 stop
Depart: Thu Sep 7 2017 Return: Sat Sep 9 2017 Trip spans 3 days
Delta
Delta
BOS
1:45a
MDW
5:50a
4h 05m
1 stop
MDW
12:15p
BOS
6:40p
6h 25m
1 stop
Depart: Sat Sep 9 2017 Return: Mon Sep 11 2017 Trip spans 3 days
Delta
Delta
BOS
1:45a
MDW
5:48a
4h 03m
1 stop
MDW
5:15a
BOS
10:59a
5h 44m
1 stop
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
4409 5:25 am 7:05 am May 20 - Jun 3
2832 5:40 am 7:15 am Jun 4 - Aug 13
2230 5:45 am 7:25 am May 30 - Jun 2
692 5:50 am 7:25 am Jun 5 - Jul 3
1727 5:55 am 7:45 am Jun 10 - Aug 12
5215 7:40 am 9:25 am Jun 4 - Aug 13
2566 7:50 am 9:30 am May 20 - Jun 3
1670 8:55 am 10:40 am May 30 - Jun 2
2660 9:45 am 11:30 am Jun 10 - Aug 12
1030 11:20 am 1:05 pm Jun 5 - Jun 30
4454 11:35 am 1:15 pm Jun 10 - Aug 12
2892 12:05 pm 1:50 pm Jun 4 - Aug 13
3260 1:50 pm 3:30 pm Jun 5 - Jun 30
3238 1:55 pm 3:35 pm May 22 - Jun 2
5316 2:00 pm 3:40 pm May 20 - Jun 3
5474 2:35 pm 4:15 pm Jun 10 - Aug 12
494 3:15 pm 4:55 pm Jun 5 - Jun 30
3396 3:55 pm 5:35 pm May 20 - Jun 3
4920 4:20 pm 6:05 pm Jun 4 - Aug 13
5386 4:30 pm 6:15 pm Jun 10 - Aug 12
776 4:35 pm 6:15 pm May 22 - Jun 2
878 5:05 pm 6:50 pm Jun 19 - Jun 30
878 5:05 pm 6:50 pm Jun 5 - Jun 16
387 7:05 pm 9:00 pm Jun 5 - Jun 30
5388 8:05 pm 9:50 pm Jun 4 - Aug 13
1552 9:00 pm 10:45 pm Jun 10 - Aug 12
3067 9:35 pm 11:15 pm Jun 4 - Aug 13
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Boston
$156
Destination

Chicago
$156
Airlines Airline reviews

6 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 9.3.

Overall
9.7
Boarding
10.0
Crew
10.0
Comfort
8.7
Food
9.0
Entertainment
8.7