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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 $471 2 $270 3 $270 4 $244 5 $249 6 $244
7 $234 8 $230 9 $230 10 $229 11 $214 12 $214 13 $293
14 $344 15 $251 16 $210 17 $284 18 $317 19 $317 20 $251
21 $395 22 $216 23 $214 24 $248 25 $318 26 $231 27 $270
28 $318 29 $230 30 $293        
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 2 - Sep 29
5059 7:50 am 11:00 am Sep 30 - Oct 30
5103 10:35 am 1:45 pm Sep 7 - Sep 28
2297 1:25 pm 4:45 pm Sep 1 - Sep 1
3223 1:25 pm 4:45 pm Sep 6 - Sep 27
6312 1:25 pm 4:45 pm Aug 31 - Aug 31
2607 3:30 pm 6:45 pm Aug 21 - Oct 31
4460 7:25 pm 10:40 pm Aug 31 - Aug 31
4780 7:35 pm 10:50 pm Sep 2 - Sep 14
4780 7:35 pm 10:50 pm Sep 16 - Sep 28
4780 7:35 pm 10:50 pm Sep 29 - Oct 30
2772 8:30 pm 11:45 pm Sep 1 - Sep 1
2839 8:30 pm 11:45 pm Sep 6 - Sep 27
2839 8:30 pm 11:45 pm Aug 30 - Aug 30