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: Mon Mar 20 2017 Return: Fri Mar 24 2017 Trip spans 5 days
Southwest
Southwest
MDW
5:45p
BOS
7:55p
2h 10m
nonstop
BOS
1:25a
MDW
4:10a
2h 45m
nonstop
Depart: Mon Feb 27 2017 Return: Tue Feb 28 2017 Trip spans 2 days
Delta
Delta
MDW
12:29p
BOS
6:09p
5h 40m
1 stop
BOS
2:00a
MDW
7:43a
5h 43m
1 stop
Depart: Tue Feb 28 2017 Return: Wed Mar 1 2017 Trip spans 2 days
Delta
Delta
MDW
4:14a
BOS
9:56a
5h 42m
1 stop
BOS
9:36a
MDW
2:04p
4h 28m
1 stop
Depart: Wed Mar 1 2017 Return: Thu Mar 2 2017 Trip spans 2 days
Delta
Delta
MDW
4:14a
BOS
8:01a
3h 47m
1 stop
BOS
6:07a
MDW
12:06p
5h 59m
1 stop
Depart: Mon Jul 10 2017 Return: Mon Jul 17 2017 Trip spans 8 days
Southwest
Southwest
MDW
6:35p
BOS
8:50p
2h 15m
nonstop
BOS
3:05p
MDW
6:00p
2h 55m
nonstop
Depart: Thu Mar 2 2017 Return: Fri Mar 3 2017 Trip spans 2 days
Delta
Delta
MDW
4:14a
BOS
9:56a
5h 42m
1 stop
BOS
1:00a
MDW
7:54a
6h 54m
1 stop
Depart: Fri Mar 3 2017 Return: Sun Mar 5 2017 Trip spans 3 days
Delta
Delta
MDW
1:40p
BOS
5:58p
4h 18m
1 stop
BOS
1:55a
MDW
8:33a
6h 38m
1 stop
Depart: Mon Mar 6 2017 Return: Tue Mar 7 2017 Trip spans 2 days
Delta
Delta
MDW
4:14a
BOS
8:01a
3h 47m
1 stop
BOS
3:40a
MDW
8:33a
4h 53m
1 stop
Depart: Tue Mar 7 2017 Return: Wed Mar 8 2017 Trip spans 2 days
Delta
Delta
MDW
4:14a
BOS
8:01a
3h 47m
1 stop
BOS
9:36a
MDW
2:04p
4h 28m
1 stop
Depart: Wed Mar 8 2017 Return: Thu Mar 9 2017 Trip spans 2 days
Delta
Delta
MDW
1:50a
BOS
8:01a
6h 11m
1 stop
BOS
6:13a
MDW
11:54a
5h 41m
1 stop
Depart: Fri Mar 10 2017 Return: Tue Mar 14 2017 Trip spans 4 days
Delta
Delta
MDW
1:45a
BOS
5:58a
4h 13m
1 stop
BOS
7:13a
MDW
12:54p
5h 41m
1 stop
Depart: Mon Mar 13 2017 Return: Tue Mar 14 2017 Trip spans 2 days
Delta
Delta
MDW
1:32p
BOS
7:07p
5h 35m
1 stop
BOS
7:13a
MDW
12:54p
5h 41m
1 stop
Depart: Tue Mar 14 2017 Return: Wed Mar 15 2017 Trip spans 2 days
Delta
Delta
MDW
2:45p
BOS
6:52p
4h 07m
1 stop
BOS
5:08a
MDW
9:28a
4h 20m
1 stop
Depart: Wed Mar 15 2017 Return: Thu Mar 16 2017 Trip spans 2 days
Delta
Delta
MDW
2:45a
BOS
9:02a
6h 17m
1 stop
BOS
1:36a
MDW
5:47a
4h 11m
1 stop
Depart: Tue Mar 21 2017 Return: Wed Mar 22 2017 Trip spans 2 days
Delta
Delta
MDW
9:03a
BOS
2:38p
5h 35m
1 stop
BOS
10:37a
MDW
3:10p
4h 33m
1 stop
Depart: Wed Mar 22 2017 Return: Thu Mar 23 2017 Trip spans 2 days
Delta
Delta
MDW
9:03a
BOS
12:55p
3h 52m
1 stop
BOS
1:36a
MDW
5:47a
4h 11m
1 stop
Depart: Tue Mar 28 2017 Return: Wed Mar 29 2017 Trip spans 2 days
Delta
Delta
MDW
12:35p
BOS
4:47p
4h 12m
1 stop
BOS
12:30p
MDW
7:11p
6h 41m
1 stop
Depart: Wed Mar 29 2017 Return: Thu Mar 30 2017 Trip spans 2 days
Delta
Delta
MDW
2:30a
BOS
8:46a
6h 16m
1 stop
BOS
1:36a
MDW
5:47a
4h 11m
1 stop
Depart: Mon Apr 3 2017 Return: Wed Apr 5 2017 Trip spans 3 days
Delta
Delta
MDW
1:27p
BOS
6:49p
5h 22m
1 stop
BOS
3:10a
MDW
8:48a
5h 38m
1 stop
Depart: Tue Apr 4 2017 Return: Wed Apr 5 2017 Trip spans 2 days
Delta
Delta
MDW
5:22a
BOS
10:52a
5h 30m
1 stop
BOS
3:10a
MDW
8:48a
5h 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
349 6:15 am 9:30 am Mar 13 - Apr 24
349 6:15 am 9:30 am Mar 9 - Mar 10
735 7:05 am 10:20 am Mar 11 - Mar 11
735 7:05 am 10:20 am Mar 18 - Apr 22
3127 7:25 am 10:40 am Feb 16 - Mar 8
3735 8:00 am 11:10 am Mar 12 - Apr 23
5152 11:30 am 2:45 pm Feb 18 - Mar 4
934 1:20 pm 4:35 pm Feb 16 - Mar 8
4074 1:45 pm 5:00 pm Mar 18 - Apr 22
4074 1:45 pm 5:00 pm Mar 11 - Mar 11
1501 2:20 pm 5:35 pm Mar 13 - Apr 24
1501 2:20 pm 5:35 pm Mar 9 - Mar 10
4348 2:25 pm 5:40 pm Feb 19 - Mar 5
5444 2:30 pm 5:45 pm Feb 18 - Mar 4
4318 2:50 pm 6:00 pm Mar 12 - Apr 16
3622 7:15 pm 10:25 pm Feb 19 - Mar 5
2037 8:55 pm 12:05 am Feb 18 - Mar 4
1146 9:00 pm 12:10 am Mar 11 - Mar 11
1146 9:00 pm 12:10 am Mar 18 - Apr 22
4309 9:10 pm 12:20 am Feb 19 - Mar 5
1443 9:45 pm 12:55 am Mar 9 - Mar 10
1443 9:45 pm 12:55 am Mar 13 - Apr 24
4211 9:45 pm 1:00 am Feb 16 - Mar 8
4177 10:15 pm 1:25 am Mar 19 - Apr 23
4177 10:15 pm 1:25 am Mar 12 - Mar 12
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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.

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^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin

Chicago
$168
Destination

Boston
$168
Airlines Airline reviews

8 travelers who booked a flight from Chicago to Boston rated their chosen airlines with an average of 8.6.

Overall
8.3
Boarding
8.8
Crew
9.0
Comfort
9.0
Food
8.5
Entertainment
8.3