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Cheap Flights from Chicago to Boston (MDW - BOS)

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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 $264 2 $213 3 $192 4 $214
5 $363 6 $214 7 $220 8 $205 9 $253 10 $388 11 $292
12 $318 13 $358 14 $184 15 $192 16 $249 17 $261 18 $190
19 $348 20 $205 21 $190 22 $249 23 $214 24 $248 25 $190
26 $317 27 $192 28 $190 29 $190 30 $192 31 $214  
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 18 - Sep 29
5102 10:35 am 1:45 pm Oct 5 - Oct 26
5103 10:35 am 1:45 pm Sep 21 - Sep 28
3222 1:25 pm 4:45 pm Oct 4 - Oct 4
3223 1:25 pm 4:45 pm Sep 20 - Sep 27
2607 3:30 pm 6:45 pm Sep 18 - Oct 31
4780 7:35 pm 10:50 pm Sep 18 - Sep 28
4780 7:35 pm 10:50 pm Sep 29 - Oct 30
2839 8:30 pm 11:45 pm Sep 20 - Sep 27
6352 8:30 pm 11:45 pm Oct 4 - Oct 25