Browse Origins:
Browse Destinations:

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: Wed May 6 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 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: Wed May 13 2015 Return: Tue May 19 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 19 2015 Return: Wed May 20 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: Wed Apr 29 2015 Trip spans 5 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: 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: 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
9:36a
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: Thu May 7 2015 Return: Tue May 12 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: Wed Apr 22 2015 Return: Tue Apr 28 2015 Trip spans 7 days
United
United
BOS
3:16a
ORD
6:04a
2h 48m
nonstop
ORD
6:41a
BOS
8:59a
2h 18m
nonstop
Depart: Tue Jun 9 2015 Return: Sat Jun 13 2015 Trip spans 5 days
American Airlines
American Airlines
BOS
2:00a
ORD
4:48a
2h 48m
nonstop
ORD
5:46p
BOS
8:08p
2h 22m
nonstop
Depart: Fri Sep 4 2015 Return: Tue Sep 8 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
BOS
4:00a
ORD
6:42a
2h 42m
nonstop
ORD
5:59a
BOS
8:14a
2h 15m
nonstop
Depart: Thu Aug 6 2015 Return: Mon Aug 10 2015 Trip spans 5 days
Delta
Delta
BOS
4:30a
MDW
10:12a
5h 42m
1 stop
MDW
1:55p
BOS
7:25p
5h 30m
1 stop
Depart: Fri Jul 10 2015 Return: Mon Jul 13 2015 Trip spans 4 days
Delta
Delta
BOS
6:30a
ORD
12:39p
6h 09m
1 stop
ORD
2:00p
BOS
7:25p
5h 25m
1 stop
Depart: Sun Jul 26 2015 Return: Wed Jul 29 2015 Trip spans 4 days
US Airways
US Airways
BOS
1:30p
ORD
6:17p
4h 47m
1 stop
ORD
5:40p
BOS
7:59p
2h 19m
nonstop
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1500 5:00 am 6:50 am May 7 - May 23
1678 5:00 am 6:50 am Apr 2 - May 6
1678 5:00 am 6:50 am Apr 4 - May 2
1488 6:00 am 7:56 am May 7 - Jun 3
289 7:40 am 9:37 am Apr 2 - May 6
289 7:43 am 9:40 am May 7 - Jun 3
160 9:05 am 10:56 am Apr 2 - Jun 3
1240 11:09 am 12:59 pm Apr 2 - May 23
1240 11:09 am 12:59 pm Apr 6 - May 20
1299 12:48 pm 2:30 pm May 9 - May 30
1299 12:48 pm 2:30 pm Apr 2 - Jun 3
1299 12:48 pm 2:30 pm Apr 4 - May 2
187 2:17 pm 4:08 pm Apr 2 - May 1
187 2:17 pm 4:08 pm May 3 - Jun 3
1404 3:45 pm 5:42 pm May 7 - May 28
1404 3:45 pm 5:42 pm May 8 - Jun 1
1415 3:45 pm 5:42 pm May 3 - May 6
1415 3:45 pm 5:42 pm Apr 3 - May 2
1415 3:45 pm 5:42 pm Apr 2 - Apr 30
1119 5:55 pm 7:55 pm Apr 2 - May 6
1119 5:55 pm 7:55 pm Apr 4 - May 2
1678 5:55 pm 7:55 pm May 9 - May 23
1678 5:55 pm 7:55 pm May 7 - May 22
40 7:20 pm 9:10 pm Apr 2 - May 8
Airports
Origin

Boston
$127
Destination

Chicago
only $127
only $184