Flights North America Canada Chicago to Canada

Flights from Chicago to Canada

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Chicago to Canada 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 Chicago to Canada by changing tabs
Quickest
Cheapest
American Airlines
American Airlines
17 Sep
ORD
11:00 pm
Chicago O'Hare Intl airport
9h 18m
1 Stop
9:18 am
+1
YYZ
Toronto Pearson Intl airport
American Airlines
19 Sep
YYZ
12:00 am
Toronto Pearson Intl airport
1h 55m
12:55 am
ORD
Chicago O'Hare Intl airport
232 USD
Porter Airlines
Porter Airlines
19 Sep
MDW
11:00 pm
Chicago Midway airport
4h 10m
1 Stop
4:10 am
+1
YUL
Montreal Pierre Elliott Trudeau Intl airport
Porter Airlines
23 Sep
YUL
12:00 am
Montreal Pierre Elliott Trudeau Intl airport
3h 42m
1 Stop
2:42 am
MDW
Chicago Midway airport
240 USD
Porter Airlines
Porter Airlines
13 Sep
MDW
11:00 pm
Chicago Midway airport
3h 55m
1 Stop
3:55 am
+1
YUL
Montreal Pierre Elliott Trudeau Intl airport
Porter Airlines
15 Sep
YUL
12:00 am
Montreal Pierre Elliott Trudeau Intl airport
6h 50m
1 Stop
5:50 am
MDW
Chicago Midway airport
241 USD
American Airlines
American Airlines
24 Oct
ORD
11:00 pm
Chicago O'Hare Intl airport
1h 43m
1:43 am
+1
YYZ
Toronto Pearson Intl airport
American Airlines
27 Oct
YYZ
12:00 am
Toronto Pearson Intl airport
2h 02m
1:02 am
ORD
Chicago O'Hare Intl airport
241 USD
Porter Airlines
Porter Airlines
02 Oct
MDW
11:00 pm
Chicago Midway airport
4h 10m
1 Stop
4:10 am
+1
YUL
Montreal Pierre Elliott Trudeau Intl airport
Porter Airlines
07 Oct
YUL
12:00 am
Montreal Pierre Elliott Trudeau Intl airport
4h 05m
1 Stop
3:05 am
MDW
Chicago Midway airport
241 USD
Porter Airlines
Porter Airlines
04 Oct
MDW
11:00 pm
Chicago Midway airport
3h 55m
1 Stop
3:55 am
+1
YUL
Montreal Pierre Elliott Trudeau Intl airport
Porter Airlines
07 Oct
YUL
12:00 am
Montreal Pierre Elliott Trudeau Intl airport
4h 46m
1 Stop
3:46 am
MDW
Chicago Midway airport
241 USD
United Airlines
United Airlines
06 Jan
ORD
11:00 pm
Chicago O'Hare Intl airport
1h 43m
1:43 am
+1
YYZ
Toronto Pearson Intl airport
United Airlines
14 Jan
YYZ
12:00 am
Toronto Pearson Intl airport
1h 52m
12:52 am
ORD
Chicago O'Hare Intl airport
257 USD
United Airlines
United Airlines
13 Sep
ORD
11:00 pm
Chicago O'Hare Intl airport
1h 44m
1:44 am
+1
YYZ
Toronto Pearson Intl airport
United Airlines
15 Sep
YYZ
12:00 am
Toronto Pearson Intl airport
1h 58m
12:58 am
ORD
Chicago O'Hare Intl airport
244 USD
American Airlines
American Airlines
24 Oct
ORD
11:00 pm
Chicago O'Hare Intl airport
1h 43m
1:43 am
+1
YYZ
Toronto Pearson Intl airport
American Airlines
27 Oct
YYZ
12:00 am
Toronto Pearson Intl airport
2h 02m
1:02 am
ORD
Chicago O'Hare Intl airport
241 USD
American Airlines
American Airlines
22 Dec
ORD
11:00 pm
Chicago O'Hare Intl airport
1h 40m
1:40 am
+1
YYZ
Toronto Pearson Intl airport
American Airlines
26 Dec
YYZ
12:00 am
Toronto Pearson Intl airport
2h 06m
1:06 am
ORD
Chicago O'Hare Intl airport
257 USD
American Airlines
American Airlines
01 Nov
ORD
11:00 pm
Chicago O'Hare Intl airport
1h 43m
1:43 am
+1
YYZ
Toronto Pearson Intl airport
American Airlines
03 Nov
YYZ
12:00 am
Toronto Pearson Intl airport
2h 06m
1:06 am
ORD
Chicago O'Hare Intl airport
257 USD
Porter Airlines
Porter Airlines
19 Sep
MDW
11:00 pm
Chicago Midway airport
4h 10m
1 Stop
4:10 am
+1
YUL
Montreal Pierre Elliott Trudeau Intl airport
Porter Airlines
23 Sep
YUL
12:00 am
Montreal Pierre Elliott Trudeau Intl airport
3h 42m
1 Stop
2:42 am
MDW
Chicago Midway airport
240 USD

Alternative routes for Chicago to Canada

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to Toronto
Fastest flight time
1h 35m
Cheapest price
198 USD
Chicago to Montreal
Fastest flight time
3h 55m
Cheapest price
241 USD
Chicago to Ottawa
Fastest flight time
3h 49m
Cheapest price
244 USD
Chicago to Calgary
Fastest flight time
3h 40m
Cheapest price
253 USD
Indianapolis to Montreal
Fastest flight time
4h 09m
Cheapest price
254 USD
Indianapolis to Québec City
Fastest flight time
4h 31m
Cheapest price
275 USD
Indianapolis to Calgary
Fastest flight time
5h 26m
Cheapest price
286 USD
Chicago to Québec City
Fastest flight time
4h 48m
Cheapest price
293 USD
Chicago to Vancouver
Fastest flight time
4h 24m
Cheapest price
303 USD
Indianapolis to Vancouver
Fastest flight time
6h 34m
Cheapest price
319 USD
Chicago to Halifax
Fastest flight time
3h 15m
Cheapest price
360 USD
Chicago to Kelowna
Fastest flight time
7h 46m
Cheapest price
360 USD
Indianapolis to Toronto
Fastest flight time
1h 33m
Cheapest price
376 USD
Chicago to Winnipeg
Fastest flight time
2h 21m
Cheapest price
383 USD
Indianapolis to Halifax
Fastest flight time
5h 19m
Cheapest price
400 USD
Chicago to Regina
Fastest flight time
6h 50m
Cheapest price
500 USD
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Flights from Chicago to:

Flights to Canada from:

  • Chicago
  • Illinois
  • United States
  • North America
Flights North America Canada Chicago to Canada