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

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.
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Book cheap flights from Boston Logan International to Chicago

(Round-trip)
Depart: Wed Sep 16 2015 Return: Tue Sep 22 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Tue Nov 10 2015 Return: Tue Dec 8 2015 Trip spans 29 days
JetBlue Airways
JetBlue Airways
BOS
5:45a
ORD
8:42a
2h 57m
nonstop
ORD
8:20a
BOS
10:36a
2h 16m
nonstop
Depart: Thu Sep 17 2015 Return: Mon Sep 21 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Sat Sep 19 2015 Return: Tue Sep 22 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Mon Sep 21 2015 Return: Tue Sep 22 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Tue Sep 22 2015 Return: Wed Sep 23 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Wed Sep 23 2015 Return: Thu Sep 24 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Thu Sep 24 2015 Return: Tue Sep 29 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Fri Sep 25 2015 Return: Sat Sep 26 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Sat Sep 26 2015 Return: Tue Sep 29 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Tue Sep 29 2015 Return: Wed Sep 30 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Wed Sep 30 2015 Return: Thu Oct 1 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Sat Oct 3 2015 Return: Mon Oct 5 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Mon Oct 5 2015 Return: Sat Oct 10 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Tue Oct 6 2015 Return: Wed Oct 7 2015 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
8:56a
ORD
11:47a
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Mon Sep 7 2015 Return: Wed Oct 7 2015 Trip spans 31 days
American Airlines
American Airlines
BOS
2:00a
ORD
4:48a
2h 48m
nonstop
ORD
3:00a
BOS
5:27a
2h 27m
nonstop
Depart: Sun Aug 30 2015 Return: Sat Sep 19 2015 Trip spans 21 days
US Airways
US Airways
BOS
3:10a
ORD
6:07a
2h 57m
nonstop
ORD
4:37p
BOS
7:04p
2h 27m
nonstop
Depart: Fri Oct 30 2015 Return: Tue Nov 3 2015 Trip spans 5 days
United
United
BOS
3:30a
ORD
6:28a
2h 58m
nonstop
ORD
4:11a
BOS
6:31a
2h 20m
nonstop
Depart: Fri Dec 11 2015 Return: Sun Dec 13 2015 Trip spans 3 days
Delta
Delta
BOS
9:43a
MDW
1:50p
4h 07m
1 stop
MDW
4:15a
BOS
9:53a
5h 38m
1 stop
Depart: Fri Nov 20 2015 Return: Mon Nov 23 2015 Trip spans 4 days
Delta
Delta
BOS
7:33a
ORD
11:49a
4h 16m
1 stop
ORD
1:00a
BOS
6:12a
5h 12m
1 stop
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 6:47 am Sep 9 - Oct 16
1500 5:00 am 6:44 am Sep 3 - Sep 8
1488 6:00 am 7:51 am Sep 9 - Oct 5
1488 6:00 am 7:48 am Sep 3 - Sep 8
289 7:10 am 9:03 am Sep 9 - Oct 16
289 7:10 am 9:07 am Sep 3 - Sep 8
160 9:00 am 10:48 am Sep 3 - Sep 8
160 9:00 am 10:54 am Sep 9 - Oct 16
2253 9:40 am 11:28 am Sep 5 - Sep 5
2253 9:40 am 11:28 am Sep 3 - Sep 8
2253 9:40 am 11:34 am Sep 12 - Oct 10
2253 9:40 am 11:34 am Sep 9 - Oct 16
1240 12:31 pm 2:22 pm Sep 9 - Oct 4
1240 12:35 pm 2:19 pm Sep 3 - Sep 8
1240 12:35 pm 2:19 pm Sep 4 - Sep 6
187 12:35 pm 2:26 pm Oct 5 - Oct 16
1435 2:10 pm 3:56 pm Oct 5 - Oct 16
187 2:10 pm 3:56 pm Sep 9 - Oct 4
187 2:10 pm 3:56 pm Sep 12 - Oct 3
187 2:12 pm 4:04 pm Sep 5 - Sep 5
187 2:12 pm 4:04 pm Sep 3 - Sep 8
1404 3:55 pm 5:44 pm Oct 5 - Oct 16
1404 3:55 pm 5:44 pm Sep 9 - Oct 4
1404 3:57 pm 5:45 pm Sep 3 - Sep 8
197 5:35 pm 7:35 pm Sep 7 - Sep 7
197 5:35 pm 7:35 pm Sep 4 - Sep 6
197 5:35 pm 7:35 pm Sep 8 - Sep 8
197 5:35 pm 7:35 pm Sep 3 - Sep 5
197 5:37 pm 7:30 pm Sep 24 - Oct 1
197 5:37 pm 7:30 pm Sep 13 - Oct 4
197 5:37 pm 7:30 pm Sep 9 - Sep 23
197 5:37 pm 7:30 pm Sep 25 - Oct 3
197 5:40 pm 7:33 pm Oct 5 - Oct 16
40 7:30 pm 9:16 pm Sep 6 - Sep 8
40 7:30 pm 9:11 pm Sep 9 - Oct 16
40 7:30 pm 9:16 pm Sep 3 - Sep 5
Airports
Origin

Boston
$81
Destination

Chicago
only $81
only $184