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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 $263 2 $245 3 $245
4 $350 5 $208 6 $208 7 $208 8 $208 9 $223 10 $208
11 $331 12 $212 13 $208 14 $208 15 $251 16 $356 17 $310
18 $316 19 $208 20 $208 21 $218 22 $285 23 $396 24 $376
25 $320 26 $366 27 $269 28 $239 29 $214 30 $208 31 $218
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!
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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
2752 8:50 am 12:05 pm Apr 27 - May 23
2752 8:50 am 12:05 pm Apr 15 - Apr 25
6389 1:15 pm 4:35 pm Apr 15 - Apr 25
6389 1:15 pm 4:35 pm Apr 27 - May 23
2222 3:30 pm 6:45 pm Apr 15 - Apr 25
2222 3:30 pm 6:45 pm Apr 27 - May 23
3724 4:50 pm 8:05 pm May 24 - May 24
5012 7:50 pm 11:05 pm May 24 - May 24
6911 7:50 pm 11:10 pm May 3 - May 17
6911 7:50 pm 11:10 pm Apr 19 - Apr 26
2998 9:00 pm 12:20 am Apr 16 - Apr 23
2998 9:00 pm 12:20 am Apr 27 - May 21