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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 Feb 3 2015 Return: Wed Feb 4 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
BOS
9:45a
ORD
12:43p
2h 58m
nonstop
ORD
8:53a
BOS
11:04a
2h 11m
nonstop
Depart: Thu Feb 5 2015 Return: Sat Feb 7 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
6:56a
ORD
9:50a
2h 54m
nonstop
ORD
6:40a
BOS
8:51a
2h 11m
nonstop
Depart: Wed Feb 4 2015 Return: Thu Feb 5 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
BOS
6:20a
ORD
9:17a
2h 57m
nonstop
ORD
1:00a
BOS
3:16a
2h 16m
nonstop
Depart: Sat Feb 7 2015 Return: Mon Feb 9 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
4:01a
ORD
6:55a
2h 54m
nonstop
ORD
9:00a
BOS
11:13a
2h 13m
nonstop
Depart: Mon Feb 9 2015 Return: Tue Feb 10 2015 Trip spans 2 days
American Airlines
American Airlines
BOS
5:07a
ORD
8:00a
2h 53m
nonstop
ORD
5:15a
BOS
7:24a
2h 09m
nonstop
Depart: Tue Feb 10 2015 Return: Wed Feb 11 2015 Trip spans 2 days
American Airlines
American Airlines
BOS
6:56a
ORD
9:50a
2h 54m
nonstop
ORD
5:15a
BOS
7:24a
2h 09m
nonstop
Depart: Wed Feb 11 2015 Return: Tue Feb 17 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
BOS
6:20a
ORD
9:17a
2h 57m
nonstop
ORD
1:00a
BOS
3:16a
2h 16m
nonstop
Depart: Wed Apr 22 2015 Return: Thu Apr 23 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:43p
2h 48m
nonstop
ORD
9:38a
BOS
12:06p
2h 28m
nonstop
Depart: Thu Apr 23 2015 Return: Fri Apr 24 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:38a
BOS
12:07p
2h 29m
nonstop
Depart: Sat Apr 25 2015 Return: Mon Apr 27 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:38a
BOS
12:07p
2h 29m
nonstop
Depart: Mon Apr 27 2015 Return: Wed Apr 29 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:38a
BOS
12:07p
2h 29m
nonstop
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
9:38a
BOS
12:07p
2h 29m
nonstop
Depart: Wed Apr 29 2015 Return: Thu Apr 30 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:38a
BOS
12:07p
2h 29m
nonstop
Depart: Thu Apr 30 2015 Return: Fri May 1 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:38a
BOS
12:07p
2h 29m
nonstop
Depart: Fri May 1 2015 Return: Sat May 2 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:38a
BOS
12:07p
2h 29m
nonstop
Depart: Sat Mar 14 2015 Return: Tue Mar 17 2015 Trip spans 4 days
United
United
BOS
6:32a
ORD
9:23a
2h 51m
nonstop
ORD
6:40a
BOS
8:55a
2h 15m
nonstop
Depart: Mon Feb 2 2015 Return: Sat Feb 14 2015 Trip spans 13 days
Multiple Airlines
Multiple Airlines
BOS
2:15a
ORD
5:17a
3h 02m
nonstop
ORD
1:35p
BOS
3:49p
2h 14m
nonstop
Depart: Fri Feb 6 2015 Return: Sun Feb 8 2015 Trip spans 3 days
Delta
Delta
BOS
1:00a
MDW
7:29a
6h 29m
1 stop
MDW
1:35p
BOS
5:34p
3h 59m
1 stop
Depart: Thu Jun 11 2015 Return: Sat Jun 13 2015 Trip spans 3 days
Delta
Delta
BOS
2:00a
ORD
7:08a
5h 08m
1 stop
ORD
2:55a
BOS
8:56a
6h 01m
1 stop
Depart: Sun Jul 19 2015 Return: Wed Jul 22 2015 Trip spans 4 days
US Airways
US Airways
BOS
1:00p
ORD
6:17p
5h 17m
1 stop
ORD
5:10a
BOS
10:30a
5h 20m
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
289 7:01 am 9:05 am Feb 19 - Feb 26
289 7:01 am 9:05 am Feb 16 - Feb 23
289 7:01 am 9:05 am Jan 29 - Feb 15
289 7:01 am 9:05 am Feb 27 - Mar 7
289 7:01 am 9:05 am Mar 8 - Mar 27
2431 8:51 am 10:45 am Feb 21 - Feb 21
2431 8:51 am 10:45 am Feb 14 - Feb 14
2431 8:51 am 10:45 am Feb 28 - Feb 28
260 9:00 am 10:54 am Mar 7 - Mar 7
2376 9:01 am 10:55 am Jan 31 - Feb 7
160 10:05 am 11:58 am Mar 5 - Mar 6
160 10:05 am 11:58 am Mar 8 - Mar 27
160 10:07 am 12:00 pm Feb 10 - Feb 10
160 10:07 am 12:00 pm Feb 8 - Feb 16
160 10:07 am 12:00 pm Feb 19 - Feb 25
160 10:07 am 12:00 pm Feb 26 - Mar 3
160 10:07 am 12:00 pm Mar 4 - Mar 4
160 10:07 am 12:00 pm Jan 30 - Feb 6
160 10:07 am 12:00 pm Feb 17 - Feb 24
187 11:56 am 1:50 pm Feb 12 - Feb 18
187 11:56 am 1:50 pm Feb 19 - Feb 23
187 11:56 am 1:50 pm Feb 24 - Mar 2
187 11:56 am 1:50 pm Mar 3 - Mar 3
187 11:56 am 1:50 pm Mar 4 - Mar 6
187 11:56 am 1:50 pm Mar 8 - Mar 27
187 11:56 am 1:50 pm Jan 29 - Feb 6
187 11:56 am 1:50 pm Jan 31 - Mar 7
187 11:56 am 1:50 pm Feb 8 - Feb 11
1551 1:56 pm 3:55 pm Feb 13 - Mar 2
1551 1:56 pm 3:55 pm Feb 18 - Mar 4
1551 1:56 pm 3:55 pm Mar 3 - Mar 6
1551 1:56 pm 3:55 pm Feb 12 - Feb 26
1551 1:56 pm 3:55 pm Mar 8 - Mar 8
1551 2:11 pm 4:10 pm Feb 1 - Feb 8
1551 2:11 pm 4:10 pm Feb 6 - Feb 11
1551 2:11 pm 4:10 pm Feb 3 - Feb 10
1063 3:40 pm 5:35 pm Mar 8 - Mar 27
1063 3:40 pm 5:35 pm Jan 29 - Mar 7
1065 4:58 pm 6:55 pm Jan 29 - Mar 7
1065 4:58 pm 6:55 pm Jan 30 - Mar 6
1065 5:03 pm 7:00 pm Mar 8 - Mar 27
1670 5:58 pm 8:00 pm Mar 8 - Mar 28
1670 5:58 pm 8:00 pm Feb 7 - Feb 13
1670 5:58 pm 8:00 pm Feb 14 - Feb 28
1670 5:58 pm 8:00 pm Feb 15 - Mar 6
1670 5:58 pm 8:00 pm Jan 29 - Feb 6
1670 5:58 pm 8:00 pm Mar 7 - Mar 7
1612 7:49 pm 9:40 pm Feb 13 - Feb 23
1612 7:49 pm 9:40 pm Mar 8 - Mar 27
1612 7:49 pm 9:40 pm Feb 24 - Feb 26
1612 7:49 pm 9:40 pm Mar 3 - Mar 5
1612 7:49 pm 9:40 pm Feb 27 - Mar 6
1612 7:49 pm 9:40 pm Feb 12 - Feb 17
1612 7:49 pm 9:40 pm Feb 19 - Feb 19
1612 7:49 pm 9:40 pm Feb 25 - Mar 4
1612 7:51 pm 9:42 pm Jan 30 - Feb 9
1612 7:51 pm 9:42 pm Feb 3 - Feb 5
1612 7:51 pm 9:42 pm Feb 10 - Feb 10
1612 7:51 pm 9:42 pm Feb 11 - Feb 11
1612 7:51 pm 9:42 pm Feb 1 - Feb 8
Airports
Origin

Boston
$133
Destination

Chicago
only $133
only $184