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Find Deals on Flights 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 Jul 28 2015 Return: Wed Aug 5 2015 Trip spans 9 days
American Airlines
American Airlines
BOS
1:00a
ORD
3:44a
2h 44m
nonstop
ORD
2:45p
BOS
5:18p
2h 33m
nonstop
Depart: Wed Aug 19 2015 Return: Tue Aug 25 2015 Trip spans 7 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 26 2015 Return: Tue Sep 1 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
BOS
4:00a
ORD
6:42a
2h 42m
nonstop
ORD
3:05a
BOS
5:23a
2h 18m
nonstop
Depart: Wed Jul 29 2015 Return: Tue Aug 4 2015 Trip spans 7 days
American Airlines
American Airlines
BOS
1:00a
ORD
3:44a
2h 44m
nonstop
ORD
9:28a
BOS
11:52a
2h 24m
nonstop
Depart: Tue Aug 25 2015 Return: Wed Aug 26 2015 Trip spans 2 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 1 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
BOS
12:50p
ORD
3:37p
2h 47m
nonstop
ORD
3:05a
BOS
5:23a
2h 18m
nonstop
Depart: Tue Sep 1 2015 Return: Wed Sep 2 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
BOS
4:00a
ORD
6:42a
2h 42m
nonstop
ORD
6:25a
BOS
8:40a
2h 15m
nonstop
Depart: Wed Sep 2 2015 Return: Tue Sep 8 2015 Trip spans 7 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 Sep 9 2015 Return: Sat Sep 12 2015 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
9:53a
ORD
12:45p
2h 52m
nonstop
ORD
9:25a
BOS
11:48a
2h 23m
nonstop
Depart: Sat Sep 12 2015 Return: Tue Sep 15 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: Sat Sep 19 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: Wed Sep 16 2015 Return: Sat Sep 19 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: 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: Tue Sep 22 2015 Return: Tue Sep 29 2015 Trip spans 8 days
JetBlue Airways
JetBlue Airways
BOS
1:00p
ORD
3:51p
2h 51m
nonstop
ORD
5:59a
BOS
8:14a
2h 15m
nonstop
Depart: Wed Sep 23 2015 Return: Tue Sep 29 2015 Trip spans 7 days
JetBlue Airways
JetBlue Airways
BOS
1:00p
ORD
3:51p
2h 51m
nonstop
ORD
5:59a
BOS
8:14a
2h 15m
nonstop
Depart: Sat Sep 26 2015 Return: Tue Sep 29 2015 Trip spans 4 days
JetBlue Airways
JetBlue Airways
BOS
3:30a
ORD
6:14a
2h 44m
nonstop
ORD
3:30p
BOS
5:47p
2h 17m
nonstop
Depart: Wed Aug 12 2015 Return: Tue Aug 18 2015 Trip spans 7 days
US Airways
US Airways
BOS
4:00a
ORD
9:39a
5h 39m
1 stop
ORD
1:00p
BOS
3:34p
2h 34m
nonstop
Depart: Mon Aug 3 2015 Return: Wed Aug 12 2015 Trip spans 10 days
United
United
BOS
5:12p
ORD
7:52p
2h 40m
nonstop
ORD
4:59p
BOS
7:30p
2h 31m
nonstop
Depart: Tue Nov 17 2015 Return: Thu Nov 19 2015 Trip spans 3 days
Delta
Delta
BOS
1:00a
MDW
8:15a
7h 15m
1 stop
MDW
4:15a
BOS
11:36a
7h 21m
1 stop
Depart: Wed Nov 25 2015 Return: Thu Nov 26 2015 Trip spans 2 days
Delta
Delta
BOS
12:00p
ORD
4:12p
4h 12m
1 stop
ORD
12:40a
BOS
4:32a
3h 52m
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 Jul 11 - Sep 8
1488 6:00 am 7:48 am Jul 6 - Sep 8
289 7:15 am 9:12 am Jul 11 - Aug 17
160 9:00 am 10:48 am Jul 11 - Sep 8
2253 9:40 am 11:28 am Aug 5 - Sep 8
2253 9:40 am 11:28 am Aug 8 - Aug 15
2253 9:45 am 11:33 am Jul 11 - Aug 1
2253 9:45 am 11:33 am Jul 2 - Aug 4
1240 12:35 pm 2:19 pm Jul 7 - Jul 30
1240 12:35 pm 2:19 pm Jul 10 - Aug 2
1240 12:35 pm 2:19 pm Aug 3 - Aug 4
1240 12:35 pm 2:19 pm Aug 5 - Aug 17
1240 12:35 pm 2:19 pm Jul 6 - Jul 27
1240 12:35 pm 2:19 pm Aug 7 - Aug 16
187 2:15 pm 4:07 pm Jul 11 - Aug 15
187 2:15 pm 4:07 pm Aug 3 - Aug 17
187 2:15 pm 4:07 pm Jul 6 - Jul 27
187 2:15 pm 4:07 pm Jul 2 - Aug 2
1404 3:57 pm 5:45 pm Jul 2 - Sep 8
197 5:35 pm 7:35 pm Jul 11 - Aug 15
197 5:35 pm 7:35 pm Jul 5 - Aug 16
197 5:35 pm 7:35 pm Jul 6 - Aug 17
40 7:30 pm 9:16 pm Jul 10 - Sep 5
40 7:30 pm 9:16 pm Jul 5 - Sep 8
Airports
Origin

Boston
$147
Destination

Chicago
only $147
only $206