Cheap flights from Canada to Chicago

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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
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
American Airlines
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
Porter Airlines
09 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
Porter Airlines
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
Porter Airlines
10 Feb.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
Porter Airlines
13 Feb.
11:00 p.m.
MDW
Chicago Midway airport
1h 37m
YTZ
1:37 a.m.
+1
Toronto Island airport
268 C$
Delta
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
Delta
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
Porter Airlines
13 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
Porter Airlines
16 Jan.
11:00 p.m.
MDW
Chicago Midway airport
1h 35m
YTZ
1:35 a.m.
+1
Toronto Island airport
281 C$
Delta
Delta
08 Jan.
12:00 a.m.
YYZ
Toronto Pearson Intl airport
5h 30m
1 Stop
MDW
4:30 a.m.
Chicago Midway airport
Delta
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
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
Air Canada
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
Porter Airlines
01 Apr.
12:00 a.m.
YTZ
Toronto Island airport
1h 50m
MDW
12:50 a.m.
Chicago Midway airport
Porter Airlines
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
Porter Airlines
09 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
Porter Airlines
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
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
United Airlines
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
Porter Airlines
13 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
Porter Airlines
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
Porter Airlines
10 Jan.
12:00 a.m.
YTZ
Toronto Island airport
1h 53m
MDW
12:53 a.m.
Chicago Midway airport
Porter Airlines
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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358 C$
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1h 39m
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359 C$
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6h 38m
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408 C$
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3h 58m
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415 C$
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11h 05m
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416 C$
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4h 12m
Cheapest price
423 C$
Halifax to Chicago
Fastest flight time
3h 34m
Cheapest price
439 C$
Kelowna to Chicago
Fastest flight time
12h 17m
Cheapest price
533 C$
Regina to Chicago
Fastest flight time
10h 35m
Cheapest price
554 C$
St. John's to Chicago
Fastest flight time
7h 45m
Cheapest price
564 C$
Moncton to Chicago
Fastest flight time
6h 15m
Cheapest price
671 C$
Halifax to Indianapolis
Fastest flight time
9h 11m
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695 C$
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