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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: Tue Jan 6 2015 Return: Wed Jan 7 2015 Trip spans 2 days
Multiple Airlines
Multiple Airlines
BOS
2:15a
ORD
5:17a
3h 02m
nonstop
ORD
9:00a
BOS
11:13a
2h 13m
nonstop
Depart: Mon Feb 2 2015 Return: Tue Feb 3 2015 Trip spans 2 days
Multiple Airlines
Multiple Airlines
BOS
9:45a
ORD
12:43p
2h 58m
nonstop
ORD
10:55a
BOS
1:06p
2h 11m
nonstop
Depart: Wed Jan 7 2015 Return: Thu Jan 8 2015 Trip spans 2 days
American Airlines
American Airlines
BOS
2:51p
ORD
5:42p
2h 51m
nonstop
ORD
9:00a
BOS
11:13a
2h 13m
nonstop
Depart: Mon Jan 19 2015 Return: Wed Jan 21 2015 Trip spans 3 days
JetBlue Airways
JetBlue Airways
BOS
2:15a
ORD
5:17a
3h 02m
nonstop
ORD
8:53a
BOS
11:04a
2h 11m
nonstop
Depart: Wed Feb 4 2015 Return: Mon Feb 9 2015 Trip spans 6 days
United
United
BOS
12:26p
ORD
3:19p
2h 53m
nonstop
ORD
1:10p
BOS
3:26p
2h 16m
nonstop
Depart: Thu Jan 8 2015 Return: Sat Jan 10 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
6:56a
ORD
9:50a
2h 54m
nonstop
ORD
6:40a
BOS
8:51a
2h 11m
nonstop
Depart: Sat Jan 10 2015 Return: Mon Jan 12 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
1:15p
ORD
4:16p
3h 01m
nonstop
ORD
1:35p
BOS
3:49p
2h 14m
nonstop
Depart: Mon Jan 12 2015 Return: Tue Jan 13 2015 Trip spans 2 days
American Airlines
American Airlines
BOS
12:58p
ORD
4:00p
3h 02m
nonstop
ORD
3:05p
BOS
5:14p
2h 09m
nonstop
Depart: Tue Jan 13 2015 Return: Thu Jan 15 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
10:40a
ORD
1:35p
2h 55m
nonstop
ORD
8:00a
BOS
10:13a
2h 13m
nonstop
Depart: Wed Jan 14 2015 Return: Thu Jan 15 2015 Trip spans 2 days
American Airlines
American Airlines
BOS
12:58p
ORD
4:00p
3h 02m
nonstop
ORD
8:00a
BOS
10:13a
2h 13m
nonstop
Depart: Thu Jan 15 2015 Return: Sat Jan 17 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
5:07a
ORD
8:00a
2h 53m
nonstop
ORD
3:05p
BOS
5:14p
2h 09m
nonstop
Depart: Sat Jan 17 2015 Return: Tue Jan 20 2015 Trip spans 4 days
American Airlines
American Airlines
BOS
12:58p
ORD
4:00p
3h 02m
nonstop
ORD
3:05p
BOS
5:14p
2h 09m
nonstop
Depart: Tue Jan 20 2015 Return: Wed Jan 21 2015 Trip spans 2 days
American Airlines
American Airlines
BOS
11:58a
ORD
2:55p
2h 57m
nonstop
ORD
5:15a
BOS
7:24a
2h 09m
nonstop
Depart: Wed Jan 21 2015 Return: Thu Jan 22 2015 Trip spans 2 days
JetBlue Airways
JetBlue Airways
BOS
2:15a
ORD
5:17a
3h 02m
nonstop
ORD
1:00a
BOS
3:16a
2h 16m
nonstop
Depart: Thu Jan 22 2015 Return: Mon Jan 26 2015 Trip spans 5 days
JetBlue Airways
JetBlue Airways
BOS
9:45a
ORD
12:43p
2h 58m
nonstop
ORD
12:20p
BOS
2:34p
2h 14m
nonstop
Depart: Sat Jan 24 2015 Return: Mon Jan 26 2015 Trip spans 3 days
American Airlines
American Airlines
BOS
10:40a
ORD
1:35p
2h 55m
nonstop
ORD
9:00a
BOS
11:13a
2h 13m
nonstop
Depart: Thu Apr 23 2015 Return: Mon Apr 27 2015 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
10:00a
ORD
12:43p
2h 43m
nonstop
ORD
9:38a
BOS
12:04p
2h 26m
nonstop
Depart: Wed Jun 24 2015 Return: Mon Jun 29 2015 Trip spans 6 days
Delta
Delta
BOS
6:30a
MDW
1:10p
6h 40m
1 stop
MDW
9:50a
BOS
3:25p
5h 35m
1 stop
Depart: Tue Jun 23 2015 Return: Thu Jun 25 2015 Trip spans 3 days
Delta
Delta
BOS
6:30a
ORD
12:39p
6h 09m
1 stop
ORD
7:05a
BOS
1:10p
6h 05m
1 stop
Depart: Sat Feb 21 2015 Return: Sun Feb 22 2015 Trip spans 2 days
US Airways
US Airways
BOS
2:00a
ORD
7:12a
5h 12m
1 stop
ORD
7:25a
BOS
1:15p
5h 50m
1 stop
Change your search
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1083 5:50 am 7:50 am Jan 2 - Jan 5
1083 5:50 am 7:50 am Dec 18 - Dec 31
1247 7:00 am 9:05 am Dec 18 - Jan 5
289 7:01 am 9:05 am Jan 6 - Feb 15
289 7:50 am 9:50 am Dec 22 - Dec 28
289 7:50 am 9:50 am Dec 31 - Jan 1
289 7:50 am 9:50 am Dec 29 - Jan 5
2376 8:55 am 10:55 am Jan 3 - Jan 3
2376 9:01 am 10:55 am Jan 10 - Feb 7
160 10:05 am 12:05 pm Dec 18 - Dec 29
160 10:05 am 12:05 pm Dec 31 - Jan 5
160 10:05 am 12:05 pm Dec 30 - Dec 30
160 10:07 am 12:00 pm Jan 6 - Jan 28
1083 11:55 am 1:50 pm Jan 1 - Jan 1
187 11:55 am 1:50 pm Dec 26 - Jan 5
187 11:55 am 1:50 pm Jan 3 - Jan 3
187 11:56 am 1:50 pm Jan 19 - Feb 2
187 11:56 am 1:50 pm Jan 10 - Mar 7
187 11:56 am 1:50 pm Jan 15 - Jan 30
187 11:56 am 1:50 pm Jan 20 - Jan 27
187 11:56 am 1:50 pm Jan 12 - Jan 14
187 11:56 am 1:50 pm Jan 6 - Jan 13
1551 1:40 pm 3:40 pm Jan 5 - Jan 5
1551 1:40 pm 3:40 pm Dec 23 - Dec 30
1551 1:40 pm 3:40 pm Dec 19 - Dec 31
1551 1:40 pm 3:40 pm Jan 1 - Jan 4
1551 2:11 pm 4:10 pm Jan 6 - Feb 3
1551 2:11 pm 4:10 pm Jan 7 - Feb 4
1551 2:11 pm 4:10 pm Jan 11 - Feb 8
1063 3:40 pm 5:45 pm Dec 18 - Jan 5
1063 3:40 pm 5:35 pm Jan 6 - Mar 7
1063 3:55 pm 6:00 pm Dec 21 - Jan 4
1065 4:58 pm 6:55 pm Jan 7 - Jan 30
1065 4:58 pm 6:55 pm Jan 6 - Jan 29
1065 5:00 pm 7:00 pm Jan 4 - Jan 5
1065 5:00 pm 7:00 pm Dec 30 - Jan 1
1065 5:00 pm 7:00 pm Dec 24 - Dec 29
1065 5:00 pm 7:00 pm Dec 27 - Jan 3
1670 5:55 pm 8:00 pm Dec 26 - Jan 5
1670 5:55 pm 8:00 pm Jan 3 - Jan 3
1670 5:58 pm 8:00 pm Jan 6 - Feb 6
1670 5:58 pm 8:00 pm Jan 17 - Jan 31
1670 6:15 pm 8:16 pm Jan 10 - Jan 10
1670 6:35 pm 8:35 pm Dec 21 - Jan 4
1612 7:50 pm 9:45 pm Dec 30 - Dec 30
1612 7:50 pm 9:45 pm Dec 21 - Jan 4
1612 7:50 pm 9:45 pm Dec 29 - Jan 5
1612 7:50 pm 9:45 pm Jan 1 - Jan 1
1612 7:51 pm 9:42 pm Jan 6 - Feb 3
1612 7:51 pm 9:42 pm Jan 8 - Jan 22
1612 7:51 pm 9:42 pm Jan 11 - Feb 8
1612 7:51 pm 9:42 pm Jan 7 - Feb 2
Airports
Origin

Boston
$130
Destination

Chicago
only $130
only $201