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Find Deals on Flights from Toronto to Chicago (YTO - CHI)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Toronto to Chicago

(Round-trip)
Depart: Wed Sep 9 2015 Return: Sat Sep 19 2015 Trip spans 11 days
Porter Airlines
Porter Airlines
YTZ
3:00a
MDW
4:50a
1h 50m
nonstop
MDW
4:00a
YTZ
5:35a
1h 35m
nonstop
Depart: Thu Sep 10 2015 Return: Sun Sep 13 2015 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
3:00a
MDW
4:50a
1h 50m
nonstop
MDW
8:30a
YTZ
10:05a
1h 35m
nonstop
Depart: Thu Sep 17 2015 Return: Sun Sep 20 2015 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
5:00a
MDW
6:50a
1h 50m
nonstop
MDW
6:00a
YTZ
7:30a
1h 30m
nonstop
Depart: Fri Sep 18 2015 Return: Sun Sep 20 2015 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
11:20a
MDW
1:10p
1h 50m
nonstop
MDW
6:00a
YTZ
7:30a
1h 30m
nonstop
Depart: Sun Sep 20 2015 Return: Sun Oct 4 2015 Trip spans 15 days
Porter Airlines
Porter Airlines
YTZ
4:15p
MDW
6:05p
1h 50m
nonstop
MDW
10:45a
YTZ
12:20p
1h 35m
nonstop
Depart: Mon Sep 21 2015 Return: Mon Oct 5 2015 Trip spans 15 days
Porter Airlines
Porter Airlines
YTZ
11:20a
MDW
1:10p
1h 50m
nonstop
MDW
9:55a
YTZ
11:30a
1h 35m
nonstop
Depart: Thu Sep 24 2015 Return: Sun Sep 27 2015 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
5:00a
MDW
6:50a
1h 50m
nonstop
MDW
3:20p
YTZ
4:55p
1h 35m
nonstop
Depart: Fri Sep 25 2015 Return: Mon Sep 28 2015 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
11:20a
MDW
1:10p
1h 50m
nonstop
MDW
2:30a
YTZ
4:05a
1h 35m
nonstop
Depart: Sat Sep 26 2015 Return: Fri Oct 2 2015 Trip spans 7 days
Porter Airlines
Porter Airlines
YTZ
8:15a
MDW
10:05a
1h 50m
nonstop
MDW
6:30a
YTZ
8:05a
1h 35m
nonstop
Depart: Sun Sep 27 2015 Return: Fri Oct 2 2015 Trip spans 6 days
Porter Airlines
Porter Airlines
YTZ
6:55a
MDW
8:45a
1h 50m
nonstop
MDW
12:50p
YTZ
2:25p
1h 35m
nonstop
Depart: Mon Sep 28 2015 Return: Fri Oct 2 2015 Trip spans 5 days
Porter Airlines
Porter Airlines
YTZ
3:00a
MDW
4:50a
1h 50m
nonstop
MDW
12:50p
YTZ
2:25p
1h 35m
nonstop
Depart: Thu Oct 1 2015 Return: Sun Oct 4 2015 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
8:25a
MDW
10:15a
1h 50m
nonstop
MDW
10:45a
YTZ
12:20p
1h 35m
nonstop
Depart: Thu Oct 15 2015 Return: Sun Oct 18 2015 Trip spans 4 days
Porter Airlines
Porter Airlines
YTZ
3:00a
MDW
4:50a
1h 50m
nonstop
MDW
10:45a
YTZ
12:20p
1h 35m
nonstop
Depart: Sun Nov 15 2015 Return: Tue Nov 17 2015 Trip spans 3 days
Porter Airlines
Porter Airlines
YTZ
3:15p
MDW
5:05p
1h 50m
nonstop
MDW
1:30a
YTZ
3:05a
1h 35m
nonstop
Depart: Sat Oct 31 2015 Return: Sun Nov 8 2015 Trip spans 9 days
Air Canada
Air Canada
YYZ
6:25a
ORD
8:19a
1h 54m
nonstop
ORD
8:45a
YYZ
10:17a
1h 32m
nonstop
Depart: Thu Oct 8 2015 Return: Sun Oct 11 2015 Trip spans 4 days
American Airlines
American Airlines
YYZ
3:15p
ORD
7:48a
16h 33m
1 stop
ORD
2:30p
YYZ
4:11p
1h 41m
nonstop
Depart: Wed Oct 7 2015 Return: Thu Oct 8 2015 Trip spans 2 days
US Airways
US Airways
YYZ
3:15p
ORD
8:38p
5h 23m
1 stop
ORD
1:40a
YYZ
6:29a
4h 49m
1 stop
Depart: Mon Aug 24 2015 Return: Wed Aug 26 2015 Trip spans 3 days
United
United
YYZ
1:18p
ORD
3:10p
1h 52m
nonstop
ORD
2:44a
YYZ
4:18a
1h 34m
nonstop
Depart: Tue Jul 14 2015 Return: Wed Jul 22 2015 Trip spans 9 days
Delta
Delta
YYZ
1:47p
MDW
5:28p
3h 41m
1 stop
MDW
11:42a
YYZ
7:11p
7h 29m
1 stop
Depart: Mon Jul 13 2015 Return: Fri Jul 17 2015 Trip spans 5 days
Delta
Delta
YYZ
5:05a
ORD
8:55a
3h 50m
1 stop
ORD
6:45a
YYZ
11:35a
4h 50m
1 stop
Direct flights YTO to CHI on American Airlines
Flight # Depart YYZ Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3523 8:15 am 9:05 am Jun 27 - Sep 8
3134 10:16 am 11:05 am Jul 6 - Sep 8
3194 11:46 am 12:25 pm Jun 28 - Aug 30
3194 11:46 am 12:25 pm Jun 27 - Sep 2
3516 3:15 pm 4:05 pm Jun 27 - Sep 8
3216 6:22 pm 7:18 pm Aug 5 - Sep 4
3216 6:22 pm 7:18 pm Jul 7 - Aug 4
3216 6:22 pm 7:18 pm Jul 6 - Aug 3
3216 6:22 pm 7:18 pm Aug 6 - Aug 20
3348 8:26 pm 9:07 pm Jul 6 - Aug 4
3348 8:26 pm 9:07 pm Jul 10 - Aug 1
3348 8:29 pm 9:10 pm Aug 6 - Aug 21
3348 8:29 pm 9:10 pm Aug 5 - Sep 2
Flight # Depart YKF Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3137 7:00 am 7:36 am Jun 27 - Sep 8
3278 3:07 pm 3:43 pm Jul 6 - Sep 8
Airports
Origin

Toronto
only $215
only $204
Destination

Chicago
only $215
only $204