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Cheap Flights from Boston to Chicago (BOS - MDW)

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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 BOS to MDW (Found by others)

Sun Mon Tue Wed Thu Fri Sat
      1 $278 2 $284 3 $284 4 $278
5 $284 6 $284 7 $249 8 $259 9 $500 10 $575 11 $264
12 $352 13 $317 14 $233 15 $199 16 $284 17 $255 18 $214
19 $342 20 $317 21 $184 22 $184 23 $234 24 $199 25 $184
26 $382 27 $214 28 $178 29 $178 30 $234 31 $199  
KAYAK searches hundreds of sites to find the best rate for your next flight from Boston to Chicago. Get the best flight deal for your Chicago trip!
Here's how it works. Search KAYAK for a flight ticket from Boston to Chicago. 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 BOS to MDW on AirTran
Flight # Depart BOS Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
2769 5:40 am 7:35 am Oct 26 - Oct 26
2769 5:40 am 7:35 am Oct 12 - Oct 19
6579 5:55 am 7:55 am Nov 8 - Nov 8
6404 6:35 am 8:30 am Oct 11 - Oct 25
3907 8:40 am 10:45 am Nov 8 - Nov 22
3978 11:45 am 1:40 pm Nov 2 - Nov 7
2745 12:25 pm 2:10 pm Sep 30 - Oct 30
2745 12:25 pm 2:10 pm Oct 5 - Oct 26
3264 12:25 pm 2:10 pm Oct 31 - Oct 31