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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 $295 2 $284 3 $270 4 $244 5 $234 6 $244
7 $293 8 $332 9 $229 10 $229 11 $229 12 $248 13 $214
14 $318 15 $292 16 $210 17 $216 18 $230 19 $251 20 $216
21 $333 22 $318 23 $214 24 $216 25 $228 26 $248 27 $230
28 $358 29 $287 30 $210        
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
2310 5:40 am 7:25 am Sep 21 - Sep 28
2310 5:40 am 7:25 am Sep 12 - Sep 15
2310 5:50 am 7:35 am Sep 7 - Sep 7
5475 6:35 am 8:15 am Aug 23 - Sep 27
6559 7:15 am 9:00 am Aug 31 - Aug 31
3736 9:05 am 10:45 am Aug 23 - Sep 27
2261 10:50 am 12:30 pm Aug 30 - Aug 30
2299 12:25 pm 2:00 pm Sep 1 - Sep 1
2745 12:25 pm 2:00 pm Sep 7 - Sep 28
2745 12:25 pm 2:10 pm Sep 30 - Oct 30
2745 12:25 pm 2:00 pm Sep 2 - Sep 29
5108 12:25 pm 2:00 pm Aug 31 - Aug 31
3464 4:20 pm 5:55 pm Aug 30 - Aug 30
3464 4:20 pm 5:55 pm Sep 6 - Sep 27