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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Boston Logan International

(Round-trip)
Depart: Mon May 16 2016 Return: Tue May 17 2016 Trip spans 2 days
Southwest
Southwest
MDW
5:40p
BOS
7:55p
2h 15m
nonstop
BOS
5:10p
MDW
7:50p
2h 40m
nonstop
Depart: Sat May 14 2016 Return: Tue May 17 2016 Trip spans 4 days
Delta
Delta
MDW
2:00a
BOS
7:37a
5h 37m
1 stop
BOS
1:25p
MDW
7:35p
6h 10m
1 stop
Depart: Tue May 17 2016 Return: Fri May 20 2016 Trip spans 4 days
Southwest
Southwest
MDW
5:40p
BOS
7:55p
2h 15m
nonstop
BOS
1:45a
MDW
4:25a
2h 40m
nonstop
Depart: Wed May 11 2016 Return: Sun May 15 2016 Trip spans 5 days
Major Airline
Major Airline
MDW
3:00a
BOS
6:57a
3h 57m
1 stop
BOS
5:00a
MDW
9:24a
4h 24m
1 stop
Depart: Tue Jun 7 2016 Return: Sat Jun 11 2016 Trip spans 5 days
Southwest
Southwest
MDW
4:35p
BOS
6:45p
2h 10m
nonstop
BOS
3:05a
MDW
5:50a
2h 45m
nonstop
Depart: Wed May 18 2016 Return: Tue May 24 2016 Trip spans 7 days
Southwest
Southwest
MDW
2:10a
BOS
4:20a
2h 10m
nonstop
BOS
1:45a
MDW
4:25a
2h 40m
nonstop
Depart: Sat Jun 4 2016 Return: Wed Jun 8 2016 Trip spans 5 days
Southwest
Southwest
MDW
4:40p
BOS
6:50p
2h 10m
nonstop
BOS
4:55p
MDW
7:35p
2h 40m
nonstop
Depart: Sat May 21 2016 Return: Wed Jun 1 2016 Trip spans 12 days
Delta
Delta
MDW
12:35p
BOS
4:53p
4h 18m
1 stop
BOS
12:40p
MDW
5:18p
4h 38m
1 stop
Depart: Thu May 19 2016 Return: Sun May 22 2016 Trip spans 4 days
Southwest
Southwest
MDW
5:40p
BOS
7:55p
2h 15m
nonstop
BOS
3:05a
MDW
5:50a
2h 45m
nonstop
Depart: Sat May 28 2016 Return: Tue May 31 2016 Trip spans 4 days
Delta
Delta
MDW
2:30a
BOS
10:12a
7h 42m
1 stop
BOS
2:06a
MDW
8:41a
6h 35m
1 stop
Depart: Wed Jun 1 2016 Return: Thu Jun 2 2016 Trip spans 2 days
Delta
Delta
MDW
2:35p
BOS
7:05p
4h 30m
1 stop
BOS
2:00a
MDW
8:44a
6h 44m
1 stop
Depart: Sat May 7 2016 Return: Sun May 8 2016 Trip spans 2 days
Southwest
Southwest
MDW
2:25p
BOS
4:40p
2h 15m
nonstop
BOS
3:05a
MDW
5:50a
2h 45m
nonstop
Depart: Mon Jun 6 2016 Return: Wed Jul 13 2016 Trip spans 38 days
Delta
Delta
MDW
1:53p
BOS
7:42p
5h 49m
1 stop
BOS
7:00a
MDW
3:36p
8h 36m
1 stop
Depart: Mon Aug 8 2016 Return: Sat Aug 13 2016 Trip spans 6 days
Major Airline
Major Airline
MDW
1:54p
BOS
7:31p
5h 37m
1 stop
BOS
12:40p
MDW
6:06p
5h 26m
1 stop
Depart: Wed Jun 8 2016 Return: Sat Jun 11 2016 Trip spans 4 days
Delta
Delta
MDW
3:00a
BOS
6:57a
3h 57m
1 stop
BOS
1:35a
MDW
6:18a
4h 43m
1 stop
Depart: Fri Jun 10 2016 Return: Sun Jun 12 2016 Trip spans 3 days
Southwest
Southwest
MDW
6:15p
BOS
8:25p
2h 10m
nonstop
BOS
1:15a
MDW
3:55a
2h 40m
nonstop
Depart: Mon Jun 13 2016 Return: Wed Jun 15 2016 Trip spans 3 days
Delta
Delta
MDW
1:57p
BOS
7:49p
5h 52m
1 stop
BOS
3:18a
MDW
10:23a
7h 05m
1 stop
Depart: Fri Jun 17 2016 Return: Mon Jun 20 2016 Trip spans 4 days
Southwest
Southwest
MDW
6:15p
BOS
8:25p
2h 10m
nonstop
BOS
1:15a
MDW
3:55a
2h 40m
nonstop
Depart: Tue Jun 14 2016 Return: Wed Jun 15 2016 Trip spans 2 days
Delta
Delta
MDW
6:59a
BOS
11:53a
4h 54m
1 stop
BOS
5:04a
MDW
9:22a
4h 18m
1 stop
Depart: Tue Jul 19 2016 Return: Wed Jul 20 2016 Trip spans 2 days
Southwest
Southwest
MDW
1:20a
BOS
3:30a
2h 10m
nonstop
BOS
1:15a
MDW
3:55a
2h 40m
nonstop
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
2936 5:20 am 8:30 am Jun 6 - Jul 1
5171 6:10 am 9:20 am May 30 - May 30
657 6:10 am 9:20 am May 31 - Jun 3
657 6:10 am 9:20 am Apr 28 - May 27
3437 6:35 am 9:45 am Apr 30 - Jun 4
466 7:05 am 10:15 am Jun 6 - Jul 1
2377 7:20 am 10:30 am Jun 5 - Jun 26
4071 7:50 am 11:10 am May 29 - May 29
2960 8:25 am 11:35 am Apr 30 - Jun 4
5598 1:20 pm 4:35 pm Jun 6 - Jul 1
5598 1:20 pm 4:35 pm Jun 5 - Jun 26
457 1:25 pm 4:45 pm Apr 30 - Jun 4
6646 1:40 pm 4:55 pm May 30 - May 30
1320 1:50 pm 5:05 pm May 29 - May 29
1597 2:05 pm 5:20 pm May 31 - Jun 3
1597 2:05 pm 5:20 pm Apr 28 - May 27
1364 5:00 pm 8:10 pm Jun 6 - Jul 1
204 5:00 pm 8:10 pm Jun 5 - Jun 26
3917 6:00 pm 9:15 pm May 28 - May 28
3917 6:25 pm 9:40 pm Jun 4 - Jun 4
3917 6:25 pm 9:40 pm Apr 30 - May 21
6360 6:40 pm 9:50 pm May 29 - May 30
2386 6:45 pm 9:55 pm Apr 28 - May 27
2386 6:45 pm 9:55 pm May 31 - Jun 3
697 8:35 pm 11:45 pm Jun 5 - Jun 17
1424 8:40 pm 11:50 pm Apr 30 - Jun 4
817 9:40 pm 12:55 am Apr 28 - May 13
817 9:40 pm 12:55 am May 15 - May 20
817 9:40 pm 12:55 am May 22 - May 27
817 9:40 pm 12:55 am May 30 - Jun 3
160 9:50 pm 1:05 am May 29 - May 29
589 10:15 pm 1:25 am Jun 5 - Jul 1
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we don't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find on occasion that certain prices are no longer available.

More questions or if you have a bad price to report to us
Please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
$112
Destination

Boston
$112