Cheap Flights from Chicago to Boston (ORD - BOS)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youth
12-17
Child
2-11
Seat Infant
under 2
Lap Infant
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none

Best fares from ORD to BOS

Sun Mon Tue Wed Thu Fri Sat
  1 $338 2 $271 3 $301 4 $251 5 $251 6 $251
7 $251 8 $251 9 $251 10 $195 11 $201 12 $201 13 $181
14 $181 15 $181 16 $161 17 $155 18 $181 19 $167 20 $147
21 $167 22 $181 23 $197 24 $147 25 $157 26 $177 27 $221
28 $223 29 $245 30 $243 31 $147      

Best fares found by others...

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!
Direct flights ORD to BOS on American Airlines
Flight # Depart ORD Arrive BOS Sun Mon Tue Wed Thu Fri Sat Valid Between
1496 8:05 am 11:10 am Dec 18 - Dec 31
1496 8:05 am 11:10 am Jan 2 - Jan 5
26 8:05 am 11:10 am Dec 2 - Dec 17
1551 9:50 am 12:55 pm Dec 23 - Dec 30
1551 9:50 am 12:55 pm Dec 7 - Dec 14
1551 9:50 am 12:55 pm Dec 18 - Dec 25
1551 9:50 am 12:55 pm Dec 19 - Dec 31
1551 9:50 am 12:55 pm Jan 1 - Jan 4
1551 10:10 am 1:15 pm Dec 3 - Dec 17
1551 10:10 am 1:15 pm Dec 9 - Dec 16
186 11:50 am 2:55 pm Dec 27 - Dec 27
186 11:50 am 2:55 pm Dec 26 - Dec 29
186 11:50 am 2:55 pm Dec 20 - Dec 20
186 11:50 am 2:55 pm Dec 13 - Dec 13
186 11:50 am 2:55 pm Dec 6 - Dec 6
186 11:50 am 2:55 pm Dec 3 - Dec 25
186 11:50 am 2:55 pm Dec 30 - Jan 5
186 11:50 am 2:55 pm Jan 3 - Jan 3
186 12:05 pm 3:10 pm Dec 7 - Jan 4
1065 1:00 pm 4:15 pm Dec 25 - Dec 25
1065 1:00 pm 4:15 pm Dec 24 - Dec 29
1065 1:00 pm 4:15 pm Dec 30 - Jan 1
1065 1:00 pm 4:15 pm Dec 6 - Dec 13
1065 1:00 pm 4:15 pm Dec 20 - Dec 27
1065 1:00 pm 4:15 pm Dec 31 - Jan 5
1065 1:00 pm 4:15 pm Dec 3 - Dec 19
1065 1:00 pm 4:15 pm Dec 2 - Dec 23
1670 2:00 pm 5:10 pm Dec 2 - Dec 24
1670 2:00 pm 5:10 pm Jan 3 - Jan 3
1670 2:00 pm 5:10 pm Dec 26 - Jan 5
1670 2:00 pm 5:10 pm Dec 6 - Dec 20
1670 2:00 pm 5:10 pm Dec 25 - Dec 27
1670 2:35 pm 5:45 pm Dec 7 - Jan 4
1612 3:55 pm 7:05 pm Dec 7 - Jan 4
1612 3:55 pm 7:05 pm Dec 20 - Dec 26
1612 3:55 pm 7:05 pm Dec 27 - Dec 27
1612 3:55 pm 7:05 pm Dec 4 - Dec 18
1612 3:55 pm 7:05 pm Dec 29 - Jan 5
1612 3:55 pm 7:05 pm Jan 3 - Jan 3
1612 3:55 pm 7:05 pm Dec 2 - Dec 23
1612 3:55 pm 7:05 pm Dec 30 - Dec 30
1612 3:55 pm 7:05 pm Dec 3 - Dec 22
1612 3:55 pm 7:05 pm Jan 1 - Jan 1
1426 6:35 pm 9:40 pm Dec 2 - Jan 1
1426 6:35 pm 9:40 pm Dec 3 - Dec 19
1426 6:35 pm 9:40 pm Dec 6 - Dec 13
1426 6:35 pm 9:40 pm Dec 20 - Dec 27
1426 6:35 pm 9:40 pm Dec 21 - Jan 4
1426 6:35 pm 9:40 pm Dec 26 - Jan 2
1426 6:35 pm 9:40 pm Dec 31 - Jan 5
1426 7:00 pm 10:05 pm Dec 7 - Dec 14
288 8:05 pm 11:10 pm Jan 1 - Jan 2
288 8:05 pm 11:10 pm Jan 4 - Jan 5
288 8:05 pm 11:10 pm Dec 10 - Dec 22
288 8:05 pm 11:10 pm Jan 3 - Jan 3
288 8:05 pm 11:10 pm Dec 27 - Dec 27
288 8:05 pm 11:10 pm Dec 26 - Dec 31
288 8:05 pm 11:10 pm Dec 23 - Dec 29
288 8:05 pm 11:10 pm Dec 6 - Dec 20
288 8:05 pm 11:10 pm Dec 3 - Dec 4
288 8:05 pm 11:10 pm Dec 2 - Dec 9
1592 8:55 pm 11:59 pm Dec 24 - Dec 29
1592 8:55 pm 11:59 pm Dec 20 - Dec 27
1592 8:55 pm 11:59 pm Dec 2 - Dec 19
1592 8:55 pm 11:59 pm Dec 30 - Jan 5
2221 10:05 pm 1:05 am Dec 3 - Dec 17
2221 10:05 pm 1:05 am Dec 19 - Dec 22
2221 10:05 pm 1:05 am Dec 28 - Jan 5
2221 10:05 pm 1:05 am Dec 30 - Jan 1
2221 10:05 pm 1:05 am Dec 2 - Dec 23