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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: Wed Jun 3 2015 Return: Wed Jun 10 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 Jun 10 2015 Return: Tue Jun 16 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: Thu Oct 1 2015 Return: Sat Oct 3 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
9:17a
ORD
12:08p
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
9:17a
ORD
12:08p
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Thu Oct 15 2015 Return: Mon Oct 19 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
9:17a
ORD
12:08p
2h 51m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Tue Jun 9 2015 Return: Sat Jun 13 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: Thu Jun 4 2015 Return: Wed Jun 24 2015 Trip spans 21 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:39a
BOS
12:08p
2h 29m
nonstop
Depart: Sat Jun 6 2015 Return: Tue Jun 16 2015 Trip spans 11 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 Jun 16 2015 Return: Wed Jun 17 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 Jun 17 2015 Return: Tue Jun 23 2015 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BOS
9:55a
ORD
12:44p
2h 49m
nonstop
ORD
9:39a
BOS
12:08p
2h 29m
nonstop
Depart: Tue Aug 18 2015 Return: Thu Aug 20 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:39a
BOS
12:05p
2h 26m
nonstop
Depart: Wed Aug 19 2015 Return: Sat Aug 22 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:39a
BOS
12:05p
2h 26m
nonstop
Depart: Thu Aug 20 2015 Return: Sat Aug 22 2015 Trip spans 3 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 22 2015 Return: Mon Aug 24 2015 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:39a
BOS
12:05p
2h 26m
nonstop
Depart: Sun Jun 14 2015 Return: Tue Jun 16 2015 Trip spans 3 days
United
United
BOS
2:10a
ORD
4:50a
2h 40m
nonstop
ORD
4:50p
BOS
7:15p
2h 25m
nonstop
Depart: Sat Jul 4 2015 Return: Wed Jul 8 2015 Trip spans 5 days
American Airlines
American Airlines
BOS
4:00a
ORD
8:21a
4h 21m
1 stop
ORD
2:56a
BOS
5:17a
2h 21m
nonstop
Depart: Mon Sep 7 2015 Return: Wed Sep 9 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
BOS
4:00a
ORD
6:42a
2h 42m
nonstop
ORD
5:59a
BOS
8:14a
2h 15m
nonstop
Depart: Sat Nov 28 2015 Return: Wed Dec 2 2015 Trip spans 5 days
Delta
Delta
BOS
5:40a
ORD
12:22p
6h 42m
1 stop
ORD
11:25a
BOS
5:32p
6h 07m
1 stop
Depart: Sun Jul 26 2015 Return: Tue Jul 28 2015 Trip spans 3 days
US Airways
US Airways
BOS
2:00a
ORD
4:48a
2h 48m
nonstop
ORD
2:56a
BOS
5:17a
2h 21m
nonstop
Depart: Fri Nov 20 2015 Return: Tue Nov 24 2015 Trip spans 5 days
Delta
Delta
BOS
11:25a
MDW
4:53p
5h 28m
1 stop
MDW
1:30p
BOS
5:32p
4h 02m
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 6:50 am May 21 - May 30
1500 5:00 am 6:50 am May 31 - Jun 3
1500 5:00 am 6:44 am Jun 4 - Jul 3
1488 6:00 am 7:56 am May 21 - Jun 3
1488 6:15 am 8:03 am Jun 4 - Jul 5
289 7:15 am 9:12 am Jun 4 - Jul 3
289 7:43 am 9:40 am May 21 - Jun 3
160 9:00 am 10:48 am Jun 4 - Jul 3
160 9:05 am 10:56 am May 21 - Jun 3
2253 9:45 am 11:33 am Jun 6 - Jun 27
2253 9:45 am 11:33 am Jun 4 - Aug 4
1240 11:09 am 12:59 pm May 21 - May 30
1240 11:09 am 12:59 pm May 31 - Jun 2
1240 11:09 am 12:59 pm May 27 - Jun 3
1240 12:35 pm 2:19 pm Jun 12 - Jul 3
1240 12:35 pm 2:19 pm Jun 4 - Jun 11
1240 12:35 pm 2:19 pm Jun 15 - Jul 2
1299 12:48 pm 2:30 pm May 23 - May 30
1299 12:48 pm 2:30 pm May 21 - Jun 3
187 2:15 pm 4:07 pm Jun 4 - Jul 5
187 2:15 pm 4:07 pm Jun 6 - Jun 27
187 2:17 pm 4:08 pm May 21 - Jun 3
1404 3:45 pm 5:42 pm Jun 3 - Jun 3
1404 3:45 pm 5:42 pm Jun 2 - Jun 2
1404 3:45 pm 5:42 pm May 22 - Jun 1
1404 3:57 pm 5:45 pm Jun 4 - Aug 17
197 5:35 pm 7:35 pm Jun 14 - Jul 1
197 5:35 pm 7:35 pm Jun 13 - Jul 2
197 5:35 pm 7:35 pm Jun 4 - Jun 12
197 5:35 pm 7:35 pm Jun 8 - Aug 17
1678 5:55 pm 7:55 pm May 31 - Jun 3
1678 5:55 pm 7:55 pm May 23 - May 30
1678 5:55 pm 7:55 pm May 21 - May 29
40 7:20 pm 9:10 pm May 21 - Jun 3
40 7:30 pm 9:16 pm Jun 14 - Aug 17
40 7:30 pm 9:16 pm Jun 4 - Jun 10
40 7:30 pm 9:16 pm Jun 11 - Jul 2
Airports
Origin

Boston
$157
Destination

Chicago
only $157
only $233