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Cheap flights from Canada to Chicago
Canada to Chicago flight comparison made easy
Below you can see the best fares for your route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Canada to Chicago by changing tabs
Quickest
Cheapest
American Airlines
10 Feb.
12:00 a.m.
YYZ
Toronto Pearson Intl airport
2h 17m
ORD
1:17 a.m.
Chicago O'Hare Intl airport
13 Feb.
11:00 p.m.
ORD
Chicago O'Hare Intl airport
5h 07m
1 Stop
YYZ
5:07 a.m.
+1
Toronto Pearson Intl airport
254 C$
Porter Airlines
09 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
10 Jan.
11:00 p.m.
MDW
Chicago Midway airport
1h 35m
YTZ
1:35 a.m.
+1
Toronto Island airport
263 C$
Porter Airlines
10 Feb.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
13 Feb.
11:00 p.m.
MDW
Chicago Midway airport
1h 37m
YTZ
1:37 a.m.
+1
Toronto Island airport
268 C$
Delta
21 Jan.
12:00 a.m.
YYZ
Toronto Pearson Intl airport
4h 58m
1 Stop
ORD
3:58 a.m.
Chicago O'Hare Intl airport
29 Jan.
11:00 p.m.
ORD
Chicago O'Hare Intl airport
1h 43m
YYZ
1:43 a.m.
+1
Toronto Pearson Intl airport
272 C$
Porter Airlines
13 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
16 Jan.
11:00 p.m.
MDW
Chicago Midway airport
1h 35m
YTZ
1:35 a.m.
+1
Toronto Island airport
281 C$
Delta
08 Jan.
12:00 a.m.
YYZ
Toronto Pearson Intl airport
5h 30m
1 Stop
MDW
4:30 a.m.
Chicago Midway airport
10 Jan.
11:00 p.m.
MDW
Chicago Midway airport
5h 02m
1 Stop
YYZ
5:02 a.m.
+1
Toronto Pearson Intl airport
283 C$
Air Canada
22 Mar.
12:00 a.m.
YYZ
Toronto Pearson Intl airport
1h 50m
ORD
12:50 a.m.
Chicago O'Hare Intl airport
27 Mar.
11:00 p.m.
ORD
Chicago O'Hare Intl airport
1h 36m
YYZ
1:36 a.m.
+1
Toronto Pearson Intl airport
313 C$
Porter Airlines
01 Apr.
12:00 a.m.
YTZ
Toronto Island airport
1h 50m
MDW
12:50 a.m.
Chicago Midway airport
05 Apr.
11:00 p.m.
MDW
Chicago Midway airport
1h 37m
YTZ
1:37 a.m.
+1
Toronto Island airport
291 C$
Porter Airlines
09 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
10 Jan.
11:00 p.m.
MDW
Chicago Midway airport
1h 35m
YTZ
1:35 a.m.
+1
Toronto Island airport
263 C$
United Airlines
10 Mar.
12:00 a.m.
YYZ
Toronto Pearson Intl airport
1h 53m
ORD
12:53 a.m.
Chicago O'Hare Intl airport
14 Mar.
11:00 p.m.
ORD
Chicago O'Hare Intl airport
1h 35m
YYZ
1:35 a.m.
+1
Toronto Pearson Intl airport
288 C$
Porter Airlines
13 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
16 Jan.
11:00 p.m.
MDW
Chicago Midway airport
1h 35m
YTZ
1:35 a.m.
+1
Toronto Island airport
281 C$
Porter Airlines
10 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
17 Jan.
11:00 p.m.
MDW
Chicago Midway airport
1h 35m
YTZ
1:35 a.m.
+1
Toronto Island airport
289 C$
Alternative routes for Canada to Chicago
Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
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*Flight prices to Chicago are based on prices for economy tickets found by momondo users during searches within the last 72 hours. These prices may no longer be available.