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 Aug 26 2015 Return: Mon Aug 31 2015 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:39a
BOS
12:05p
2h 26m
nonstop
Depart: Tue Sep 1 2015 Return: Sat Sep 12 2015 Trip spans 12 days
United
United
BOS
5:30a
ORD
8:14a
2h 44m
nonstop
ORD
3:30a
BOS
5:53a
2h 23m
nonstop
Depart: Tue Oct 6 2015 Return: Wed Oct 7 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
BOS
3:11a
ORD
5:55a
2h 44m
nonstop
ORD
5:36a
BOS
7:53a
2h 17m
nonstop
Depart: Wed Oct 28 2015 Return: Sat Oct 31 2015 Trip spans 4 days
American Airlines
American Airlines
BOS
2:00a
ORD
4:51a
2h 51m
nonstop
ORD
11:10a
BOS
1:37p
2h 27m
nonstop
Depart: Thu Aug 27 2015 Return: Mon Aug 31 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:39a
BOS
12:05p
2h 26m
nonstop
Depart: Sat Aug 29 2015 Return: Tue Sep 15 2015 Trip spans 18 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Sun Aug 30 2015 Return: Tue Sep 15 2015 Trip spans 17 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Wed Sep 2 2015 Return: Wed Sep 9 2015 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:39a
BOS
12:05p
2h 26m
nonstop
Depart: Sat Sep 5 2015 Return: Wed Sep 9 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:39a
BOS
12:05p
2h 26m
nonstop
Depart: Tue Sep 8 2015 Return: Sat Sep 19 2015 Trip spans 12 days
United
United
BOS
12:22p
ORD
3:10p
2h 48m
nonstop
ORD
5:10p
BOS
7:35p
2h 25m
nonstop
Depart: Wed Sep 9 2015 Return: Sat Sep 19 2015 Trip spans 11 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Thu Sep 10 2015 Return: Tue Sep 15 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: Mon Sep 14 2015 Return: Thu Sep 17 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 15 2015 Return: Wed Sep 16 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 16 2015 Return: Thu Sep 17 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 17 2015 Return: Sat Sep 19 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 Sep 21 2015 Return: Sat Sep 26 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: Thu Oct 8 2015 Return: Tue Oct 13 2015 Trip spans 6 days
US Airways
US Airways
BOS
1:30a
ORD
6:19a
4h 49m
1 stop
ORD
2:45p
BOS
6:58p
4h 13m
1 stop
Depart: Wed Dec 9 2015 Return: Sat Dec 12 2015 Trip spans 4 days
Delta
Delta
BOS
7:30a
MDW
1:50p
6h 20m
1 stop
MDW
7:40a
BOS
11:30a
3h 50m
1 stop
Depart: Tue Dec 29 2015 Return: Tue Jan 5 2016 Trip spans 8 days
Delta
Delta
BOS
4:15a
ORD
8:40a
4h 25m
1 stop
ORD
7:00a
BOS
11:36a
4h 36m
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 6:44 am Aug 6 - Sep 8
1488 6:00 am 7:48 am Aug 6 - Sep 8
289 7:10 am 9:07 am Aug 18 - Sep 8
289 7:15 am 9:12 am Aug 6 - Aug 17
160 9:00 am 10:48 am Aug 6 - Sep 8
2253 9:40 am 11:28 am Aug 6 - Sep 8
2253 9:40 am 11:28 am Aug 8 - Aug 15
2253 9:40 am 11:28 am Aug 22 - Sep 5
1240 12:35 pm 2:19 pm Sep 3 - Sep 8
1240 12:35 pm 2:19 pm Aug 21 - Aug 30
1240 12:35 pm 2:19 pm Sep 4 - Sep 6
1240 12:35 pm 2:19 pm Aug 20 - Aug 27
1240 12:35 pm 2:19 pm Aug 18 - Sep 2
1240 12:35 pm 2:19 pm Aug 7 - Aug 16
1240 12:35 pm 2:19 pm Aug 6 - Aug 17
187 2:12 pm 4:04 pm Aug 22 - Sep 5
187 2:12 pm 4:04 pm Aug 18 - Sep 8
187 2:15 pm 4:07 pm Aug 8 - Aug 15
187 2:15 pm 4:07 pm Aug 6 - Aug 17
1404 3:57 pm 5:45 pm Aug 6 - Sep 8
197 5:35 pm 7:35 pm Aug 20 - Sep 5
197 5:35 pm 7:35 pm Aug 10 - Aug 17
197 5:35 pm 7:35 pm Aug 19 - Sep 6
197 5:35 pm 7:35 pm Aug 18 - Sep 1
197 5:35 pm 7:35 pm Aug 7 - Aug 16
197 5:35 pm 7:35 pm Aug 6 - Aug 15
197 5:35 pm 7:35 pm Sep 8 - Sep 8
197 5:35 pm 7:35 pm Sep 7 - Sep 7
40 7:30 pm 9:16 pm Aug 6 - Sep 5
40 7:30 pm 9:16 pm Aug 9 - Sep 8
Airports
Origin

Boston
$81
Destination

Chicago
only $81
only $184