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Find Flight Deals from Boston Logan International to Chicago (BOS - CHI)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Boston Logan International to Chicago

(Round-trip)
Depart: Tue Apr 28 2015 Return: Wed Apr 29 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Wed Apr 29 2015 Return: Tue May 5 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Tue May 5 2015 Return: Tue May 12 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Wed May 6 2015 Return: Tue May 12 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Tue May 12 2015 Return: Wed May 13 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Sat Apr 25 2015 Return: Tue Apr 28 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Sat May 2 2015 Return: Tue May 5 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Mon May 4 2015 Return: Tue May 5 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Sat May 9 2015 Return: Tue May 12 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Sat May 16 2015 Return: Tue May 19 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Thu Apr 23 2015 Return: Tue Apr 28 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Mon Apr 27 2015 Return: Tue Apr 28 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Thu Apr 30 2015 Return: Tue May 5 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:36a
BOS
12:05p
2h 29m
nonstop
Depart: Mon Apr 13 2015 Return: Wed Apr 15 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
3:20p
ORD
6:10p
2h 50m
nonstop
ORD
3:05a
BOS
5:22a
2h 17m
nonstop
Depart: Fri Apr 24 2015 Return: Tue Apr 28 2015 Trip spans 5 days
United
United
BOS
2:05a
ORD
4:53a
2h 48m
nonstop
ORD
4:57p
BOS
7:15p
2h 18m
nonstop
Depart: Sun May 3 2015 Return: Mon May 4 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
BOS
4:05a
ORD
6:52a
2h 47m
nonstop
ORD
3:10p
BOS
5:30p
2h 20m
nonstop
Depart: Thu Apr 16 2015 Return: Mon Apr 20 2015 Trip spans 5 days
US Airways
US Airways
BOS
2:45a
ORD
9:07a
6h 22m
1 stop
ORD
3:05a
BOS
5:22a
2h 17m
nonstop
Depart: Tue Mar 24 2015 Return: Wed Mar 25 2015 Trip spans 2 days
Multiple Airlines
Multiple Airlines
BOS
10:50a
ORD
1:41p
2h 51m
nonstop
ORD
10:00a
BOS
12:13p
2h 13m
nonstop
Depart: Tue Jul 7 2015 Return: Tue Jul 21 2015 Trip spans 15 days
Delta
Delta
BOS
3:10a
MDW
9:15a
6h 05m
1 stop
MDW
5:15a
BOS
10:53a
5h 38m
1 stop
Depart: Fri Mar 13 2015 Return: Mon Mar 16 2015 Trip spans 4 days
Delta
Delta
BOS
1:55a
ORD
6:17a
4h 22m
1 stop
ORD
5:04a
BOS
9:00a
3h 56m
1 stop
Change your search
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1678 5:00 am 6:50 am Mar 29 - May 6
1678 5:00 am 6:50 am Apr 4 - May 2
289 7:01 am 9:05 am Mar 8 - Mar 27
289 7:01 am 9:05 am Mar 14 - Mar 21
289 7:01 am 9:05 am Mar 5 - Mar 7
289 7:01 am 9:05 am Mar 28 - Mar 28
289 7:40 am 9:37 am Mar 30 - May 6
260 8:30 am 10:24 am Mar 14 - Mar 28
260 8:30 am 10:24 am Mar 7 - Mar 7
160 9:05 am 10:56 am Mar 29 - May 20
160 10:05 am 11:58 am Mar 5 - Mar 6
160 10:05 am 11:58 am Mar 8 - Mar 27
160 10:05 am 11:58 am Mar 9 - Mar 25
1240 11:09 am 12:59 pm Mar 29 - May 19
1240 11:09 am 12:59 pm Mar 30 - May 20
187 11:56 am 1:50 pm Mar 28 - Mar 28
187 11:56 am 1:50 pm Mar 14 - Mar 21
187 11:56 am 1:50 pm Mar 10 - Mar 24
187 11:56 am 1:50 pm Mar 8 - Mar 27
187 11:56 am 1:50 pm Mar 7 - Mar 7
187 11:56 am 1:50 pm Mar 5 - Mar 6
1299 12:48 pm 2:30 pm Apr 4 - May 2
1299 12:48 pm 2:30 pm Mar 29 - May 20
1551 1:56 pm 3:55 pm Mar 5 - Mar 6
1551 1:56 pm 3:55 pm Mar 9 - Mar 27
1551 1:56 pm 3:55 pm Mar 8 - Mar 8
187 2:17 pm 4:08 pm Mar 29 - May 1
1063 3:40 pm 5:35 pm Mar 28 - Mar 28
1063 3:40 pm 5:35 pm Mar 8 - Mar 27
1063 3:40 pm 5:35 pm Mar 5 - Mar 7
1415 3:45 pm 5:42 pm Mar 31 - Apr 30
1415 3:45 pm 5:42 pm Mar 29 - May 2
1065 4:58 pm 6:55 pm Mar 6 - Mar 6
1065 4:58 pm 6:55 pm Mar 5 - Mar 7
1065 5:03 pm 7:00 pm Mar 8 - Mar 27
1065 5:03 pm 7:00 pm Mar 10 - Mar 26
1119 5:55 pm 7:55 pm Mar 29 - May 6
1119 5:55 pm 7:55 pm Apr 4 - May 2
1670 5:58 pm 8:00 pm Mar 5 - Mar 7
1670 5:58 pm 8:00 pm Mar 8 - Mar 28
40 7:20 pm 9:10 pm Mar 29 - May 8
1612 7:49 pm 9:40 pm Mar 6 - Mar 6
1612 7:49 pm 9:40 pm Mar 8 - Mar 27
Airports
Origin

Boston
$127
Destination

Chicago
only $127
only $184