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Cheap Flights from Chicago to Boston (MDW - BOS)

DepartReturn
1 adult
Note: some airlines charge for infants in laps.
The price shown for each flight will be the average for all passengers including any infants.
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Best fares from MDW to BOS (Found by others)

Sun Mon Tue Wed Thu Fri Sat
  1 $374 2 $258 3 $308 4 $324 5 $324 6 $306
7 $314 8 $314 9 $306 10 $314 11 $281 12 $281 13 $192
14 $306 15 $192 16 $192 17 $234 18 $386 19 $386 20 $192
21 $386 22 $192 23 $192 24 $192 25 $353 26 $264 27 $239
28 $306 29 $386 30 $186        
KAYAK searches hundreds of sites to find the best rate for your next flight from Chicago to Boston. Get the best flight deal for your Boston trip!
Here's how it works. Search KAYAK for a flight ticket from Chicago to Boston. Sort, filter and compare results on one web page. Then book your plane ticket direct on the airline or travel agent site of your choice!
Select an airline:  AirTran
Direct flights MDW to BOS on AirTran
Flight # Depart MDW Arrive BOS Sun Mon Tue Wed Thu Fri Sat Valid Between
5059 7:50 am 11:00 am Sep 30 - Oct 30
5059 7:50 am 11:00 am Sep 2 - Sep 8
5059 7:50 am 11:00 am Sep 9 - Sep 29
5102 10:35 am 1:45 pm Oct 5 - Oct 26
5103 10:35 am 1:45 pm Sep 14 - Sep 28
3222 1:25 pm 4:45 pm Oct 4 - Oct 4
3223 1:25 pm 4:45 pm Sep 13 - Sep 27
2607 3:30 pm 6:45 pm Aug 28 - Sep 8
2607 3:30 pm 6:45 pm Sep 9 - Oct 31
4780 7:35 pm 10:50 pm Sep 29 - Oct 30
4780 7:35 pm 10:50 pm Sep 9 - Sep 28
4780 7:35 pm 10:50 pm Sep 7 - Sep 8
2839 8:30 pm 11:45 pm Sep 13 - Sep 27
6352 8:30 pm 11:45 pm Oct 4 - Oct 25