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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 $252 2 $249 3 $234 4 $249
5 $252 6 $317 7 $199 8 $199 9 $283 10 $503 11 $302
12 $237 13 $302 14 $249 15 $199 16 $255 17 $292 18 $199
19 $382 20 $277 21 $184 22 $184 23 $199 24 $230 25 $184
26 $397 27 $255 28 $178 29 $178 30 $199 31 $214  
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 3 - Oct 5
2769 5:40 am 7:35 am Oct 12 - Oct 19
2769 5:40 am 7:35 am Oct 26 - Oct 26
6404 6:35 am 8:30 am Oct 4 - Oct 4
6404 6:35 am 8:30 am Oct 11 - Oct 25
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