SEARCH ONE AND DONE. - Compare hundreds of travel sites at once.
Choose where to book.
Find deals from over 400 airlines worldwide.

Cheap Flights from Boston to Chicago (BOS - CHI)

DepartReturn
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.

Best fares from BOS to CHI (Found by others)

Sun Mon Tue Wed Thu Fri Sat
          1 $309 2 $285
3 $276 4 $276 5 $276 6 $276 7 $276 8 $276 9 $302
10 $341 11 $254 12 $301 13 $265 14 $232 15 $274 16 $234
17 $214 18 $199 19 $195 20 $195 21 $195 22 $215 23 $195
24 $214 25 $195 26 $175 27 $175 28 $199 29 $214 30 $175
31 $195            
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!
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1083 6:00 am 7:45 am Jul 31 - Aug 4
1083 6:00 am 7:45 am Aug 5 - Aug 18
1083 6:00 am 7:40 am Aug 22 - Oct 31
1327 7:10 am 9:00 am Jul 31 - Aug 30
1327 7:10 am 9:00 am Sep 1 - Oct 1
289 8:00 am 9:45 am Jul 31 - Oct 24
2376 9:05 am 10:55 am Sep 1 - Oct 31
2376 9:05 am 10:50 am Jul 31 - Aug 18
2376 9:05 am 10:55 am Aug 19 - Aug 31
2376 9:05 am 10:55 am Aug 23 - Aug 30
26 10:10 am 11:50 am Sep 1 - Oct 24
26 10:10 am 11:50 am Jul 31 - Aug 29
26 10:10 am 11:50 am Aug 31 - Aug 31
26 10:10 am 11:50 am Aug 2 - Aug 16
1551 11:55 am 1:35 pm Aug 21 - Aug 31
1551 11:55 am 1:35 pm Aug 23 - Sep 27
1551 11:55 am 1:35 pm Sep 4 - Sep 29
1551 11:55 am 1:35 pm Aug 19 - Sep 3
1551 11:55 am 1:35 pm Aug 3 - Aug 17
1551 11:55 am 1:35 pm Aug 1 - Aug 18
1661 1:55 pm 3:40 pm Jul 31 - Aug 18
1661 2:00 pm 3:45 pm Aug 19 - Aug 31
1661 2:00 pm 3:45 pm Sep 1 - Oct 1
187 4:30 pm 6:15 pm Aug 19 - Oct 1
187 4:40 pm 6:30 pm Jul 31 - Aug 18
1299 5:25 pm 7:15 pm Aug 19 - Sep 15
1299 5:50 pm 7:40 pm Jul 31 - Aug 18
1624 6:15 pm 8:00 pm Aug 21 - Aug 30
1624 6:15 pm 8:00 pm Sep 1 - Oct 24
1624 6:15 pm 8:00 pm Aug 19 - Aug 29
1624 6:35 pm 8:15 pm Aug 24 - Aug 31
1624 6:45 pm 8:30 pm Aug 1 - Aug 18
1624 6:45 pm 8:30 pm Jul 31 - Aug 17
1612 7:50 pm 9:30 pm Aug 20 - Aug 29
1612 7:50 pm 9:30 pm Aug 19 - Aug 28
1612 7:50 pm 9:30 pm Sep 2 - Sep 4
1612 7:50 pm 9:30 pm Sep 1 - Sep 19
1612 7:50 pm 9:30 pm Aug 31 - Aug 31
1612 7:55 pm 9:35 pm Aug 2 - Aug 16
1612 7:55 pm 9:35 pm Aug 8 - Aug 18
1612 7:55 pm 9:35 pm Jul 31 - Aug 6