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: Thu Oct 13 2016 Return: Tue Oct 18 2016 Trip spans 6 days
Depart: Wed Oct 12 2016 Return: Sat Oct 15 2016 Trip spans 4 days
Depart: Wed Oct 26 2016 Return: Wed Nov 9 2016 Trip spans 15 days
Depart: Tue Oct 11 2016 Return: Tue Oct 18 2016 Trip spans 8 days
Depart: Sat Oct 29 2016 Return: Mon Oct 31 2016 Trip spans 3 days
Depart: Tue Nov 1 2016 Return: Sun Nov 6 2016 Trip spans 6 days
Depart: Thu Sep 15 2016 Return: Sat Oct 15 2016 Trip spans 31 days
Depart: Wed Sep 28 2016 Return: Sun Oct 2 2016 Trip spans 5 days
Depart: Sat Oct 1 2016 Return: Sun Oct 2 2016 Trip spans 2 days
Depart: Wed Oct 19 2016 Return: Thu Oct 20 2016 Trip spans 2 days
Depart: Fri Oct 28 2016 Return: Wed Nov 2 2016 Trip spans 6 days
Depart: Mon Nov 7 2016 Return: Wed Nov 9 2016 Trip spans 3 days
Depart: Wed Sep 14 2016 Return: Sun Sep 18 2016 Trip spans 5 days
Depart: Fri Sep 16 2016 Return: Sun Sep 18 2016 Trip spans 3 days
Depart: Thu Sep 8 2016 Return: Tue Sep 13 2016 Trip spans 6 days
Depart: Sat Sep 17 2016 Return: Wed Sep 21 2016 Trip spans 5 days
Depart: Tue Sep 20 2016 Return: Wed Sep 21 2016 Trip spans 2 days
Depart: Thu Sep 29 2016 Return: Sun Oct 2 2016 Trip spans 4 days
Depart: Wed Sep 21 2016 Return: Sat Sep 24 2016 Trip spans 4 days
Depart: Thu Nov 3 2016 Return: Mon Nov 7 2016 Trip spans 5 days
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 Sep 6 - Sep 9
493 6:00 am 9:10 am Sep 11 - Sep 30
493 6:00 am 9:10 am Aug 25 - Sep 2
493 6:00 am 9:10 am Oct 2 - Nov 4
1144 6:20 am 9:40 am Sep 3 - Sep 3
1700 6:20 am 9:40 am Sep 10 - Oct 1
654 7:15 am 10:30 am Sep 5 - Sep 5
1859 9:00 am 12:30 pm Sep 4 - Sep 4
1192 11:30 am 2:45 pm Sep 6 - Sep 30
1192 11:30 am 2:45 pm Aug 25 - Sep 2
1195 11:30 am 2:45 pm Sep 3 - Sep 3
1260 11:30 am 2:45 pm Oct 2 - Oct 28
1562 11:30 am 2:45 pm Sep 5 - Sep 5
918 11:30 am 2:45 pm Sep 10 - Oct 1
2288 1:40 pm 5:05 pm Sep 6 - Sep 30
2288 1:40 pm 5:05 pm Sep 5 - Sep 5
2288 1:40 pm 5:05 pm Aug 25 - Sep 2
2288 1:40 pm 5:00 pm Oct 2 - Nov 4
934 1:40 pm 5:05 pm Sep 4 - Sep 4
2939 1:55 pm 5:20 pm Sep 3 - Sep 3
3705 1:55 pm 5:20 pm Sep 10 - Oct 1
554 5:15 pm 8:30 pm Sep 5 - Sep 5
1435 5:20 pm 8:35 pm Sep 6 - Sep 30
1435 5:20 pm 8:35 pm Aug 25 - Sep 2
678 5:20 pm 8:35 pm Oct 2 - Oct 30
2614 5:30 pm 8:50 pm Sep 10 - Oct 1
2442 5:40 pm 8:55 pm Sep 4 - Sep 4
3668 8:55 pm 12:05 am Aug 27 - Oct 29
5292 9:50 pm 1:00 am Sep 4 - Sep 4
484 9:55 pm 1:05 am Sep 6 - Sep 30
484 9:55 pm 1:05 am Oct 2 - Oct 21
484 9:55 pm 1:05 am Aug 25 - Sep 2
484 10:00 pm 1:15 am Sep 5 - Sep 5
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

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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 can'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.

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Airports
Origin

Chicago
$72
Destination

Boston
$72
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