Flights North America Canada Chicago to Canada

Cheap flights from Chicago to Canada

Depart
Return
Any month
Compare vs. momondo |

Easily compare round-trip flights from Chicago to Canada

Below you can see the best fares for your round-trip flight 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
United Airlines
United Airlines
23 Jan
11:00 pm
ORD
Chicago O'Hare Intl airport
4h 13m
YYC
2:13 am
+1
Calgary airport
United Airlines
30 Jan
10:00 pm
YYC
Calgary airport
3h 42m
ORD
2:42 am
+1
Chicago O'Hare Intl airport
$163
United Airlines
United Airlines
11 Apr
11:00 pm
ORD
Chicago O'Hare Intl airport
8h 15m
1 Stop
YYC
6:15 am
+1
Calgary airport
United Airlines
15 Apr
10:00 pm
YYC
Calgary airport
3h 46m
ORD
2:46 am
+1
Chicago O'Hare Intl airport
$172
United Airlines
United Airlines
14 Apr
11:00 pm
ORD
Chicago O'Hare Intl airport
3h 46m
YYC
1:46 am
+1
Calgary airport
United Airlines
22 Apr
10:00 pm
YYC
Calgary airport
3h 46m
ORD
2:46 am
+1
Chicago O'Hare Intl airport
$190
American Airlines
American Airlines
05 Mar
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 42m
YYZ
1:42 am
+1
Toronto Pearson Intl airport
American Airlines
08 Mar
12:00 am
YYZ
Toronto Pearson Intl airport
1h 50m
ORD
12:50 am
Chicago O'Hare Intl airport
$194
American Airlines
American Airlines
11 Apr
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 45m
YYZ
1:45 am
+1
Toronto Pearson Intl airport
American Airlines
14 Apr
12:00 am
YYZ
Toronto Pearson Intl airport
1h 59m
ORD
12:59 am
Chicago O'Hare Intl airport
$196
United Airlines
United Airlines
27 Feb
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 37m
YYZ
1:37 am
+1
Toronto Pearson Intl airport
United Airlines
01 Mar
12:00 am
YYZ
Toronto Pearson Intl airport
2h 17m
ORD
1:17 am
Chicago O'Hare Intl airport
$205
American Airlines
American Airlines
05 Mar
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 42m
YYZ
1:42 am
+1
Toronto Pearson Intl airport
American Airlines
08 Mar
12:00 am
YYZ
Toronto Pearson Intl airport
1h 50m
ORD
12:50 am
Chicago O'Hare Intl airport
$194
Major Airline
Major Airline
28 May
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 40m
YYZ
1:40 am
+1
Toronto Pearson Intl airport
Major Airline
02 Jun
12:00 am
YYZ
Toronto Pearson Intl airport
1h 53m
ORD
12:53 am
Chicago O'Hare Intl airport
$220
American Airlines
American Airlines
08 May
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 40m
YYZ
1:40 am
+1
Toronto Pearson Intl airport
American Airlines
10 May
12:00 am
YYZ
Toronto Pearson Intl airport
1h 59m
ORD
12:59 am
Chicago O'Hare Intl airport
$226
American Airlines
American Airlines
11 Apr
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 45m
YYZ
1:45 am
+1
Toronto Pearson Intl airport
American Airlines
14 Apr
12:00 am
YYZ
Toronto Pearson Intl airport
1h 59m
ORD
12:59 am
Chicago O'Hare Intl airport
$196
American Airlines
American Airlines
21 Feb
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 48m
YYZ
1:48 am
+1
Toronto Pearson Intl airport
American Airlines
23 Feb
12:00 am
YYZ
Toronto Pearson Intl airport
2h 05m
ORD
1:05 am
Chicago O'Hare Intl airport
$240
United Airlines
United Airlines
27 Feb
11:00 pm
ORD
Chicago O'Hare Intl airport
1h 37m
YYZ
1:37 am
+1
Toronto Pearson Intl airport
United Airlines
01 Mar
12:00 am
YYZ
Toronto Pearson Intl airport
2h 17m
ORD
1:17 am
Chicago O'Hare Intl airport
$205

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 Calgary
Fastest flight time
3h 42m
Cheapest price
$163
Chicago to Toronto
Fastest flight time
1h 35m
Cheapest price
$189
Indianapolis to Montreal
Fastest flight time
4h 18m
Cheapest price
$216
Chicago to Montreal
Fastest flight time
3h 45m
Cheapest price
$249
Chicago to Ottawa
Fastest flight time
3h 39m
Cheapest price
$256
Indianapolis to Calgary
Fastest flight time
5h 32m
Cheapest price
$268
Indianapolis to Vancouver
Fastest flight time
6h 16m
Cheapest price
$274
Chicago to Québec City
Fastest flight time
4h 38m
Cheapest price
$302
Chicago to Winnipeg
Fastest flight time
2h 23m
Cheapest price
$306
Indianapolis to Québec City
Fastest flight time
4h 36m
Cheapest price
$330
Chicago to Vancouver
Fastest flight time
4h 24m
Cheapest price
$348
Chicago to Halifax
Fastest flight time
3h 12m
Cheapest price
$355
Chicago to Kelowna
Fastest flight time
6h 59m
Cheapest price
$360
Indianapolis to Toronto
Fastest flight time
1h 36m
Cheapest price
$365
Indianapolis to Halifax
Fastest flight time
6h 08m
Cheapest price
$396
Chicago to Regina
Fastest flight time
7h 05m
Cheapest price
$594
View more

Flights from Chicago to:

*Flight prices to Canada 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.
Flights North America Canada Chicago to Canada