Find Cheap Flights from Chicago to Canada
Flights to Canada
Return flight deals:
Canada - Chicago
Browse Origins:
- Flights »
- United States »
- Chicago:
- Chicago Midway $202
- Chicago O'Hare International $220
Browse Destinations:
- Flights »
- Worldwide »
- North America »
- Canada:
- Abbotsford $639
- Calgary $317
- Charlottetown (Prince Edward Island) $478
- Deer Lake $498
- Edmonton $307
- Fort St John $485
- Fredericton $504
- Halifax Intl $328
- Hamilton $321
- Kamloops $779
- Kelowna $423
- Kitchener-Waterloo $811
- London Airport $388
- Moncton Intl $444
- Montreal $260
- Ottawa $298
- Québec City $354
- Red Deer $659
- Regina $396
- Saint John $423
- Saskatoon $310
- St John's $422
- Sudbury $339
- Thunder Bay $297
- Toronto $202
- Vancouver $340
- Victoria Intl $343
- Windsor $923
- Winnipeg $447
Dates flexible? Here are the best fares found in the past 48 hours...
Book cheap flights from Chicago to Canada
(Round-trip)
Depart: Fri Oct 6 2017
Return: Tue Oct 10 2017
Trip spans 5 days
$202
Select
Porter Airlines
MDW
→
YTZ
1h 45m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Sat Sep 16 2017
Return: Tue Sep 19 2017
Trip spans 4 days
$212
Select
Major Airline
MDW
→
YTZ
1h 40m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Wed Sep 27 2017
Return: Sun Oct 1 2017
Trip spans 5 days
$329
Select
Delta
MDW
→
YEG
11h 43m
2 stops
YEG
→
MDW
7h 19m
1 stop
Depart: Fri Oct 13 2017
Return: Sun Oct 15 2017
Trip spans 3 days
$212
Select
Porter Airlines
MDW
→
YTZ
1h 45m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Fri Jan 12 2018
Return: Sun Jan 14 2018
Trip spans 3 days
$457
Select
Multiple Airlines
MDW
→
YQB
10h 09m
2 stops
YQB
→
MDW
6h 25m
1 stop
Depart: Thu Aug 10 2017
Return: Tue Aug 29 2017
Trip spans 20 days
$216
Select
Porter Airlines
MDW
→
YTZ
1h 40m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Wed Sep 6 2017
Return: Fri Sep 8 2017
Trip spans 3 days
$216
Select
Porter Airlines
MDW
→
YTZ
1h 40m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Thu Nov 30 2017
Return: Sun Dec 3 2017
Trip spans 4 days
$216
Select
Porter Airlines
MDW
→
YTZ
1h 37m
nonstop
YTZ
→
MDW
1h 50m
nonstop
Depart: Thu Dec 7 2017
Return: Sun Dec 10 2017
Trip spans 4 days
$216
Select
Porter Airlines
MDW
→
YTZ
1h 37m
nonstop
YTZ
→
MDW
1h 50m
nonstop
Depart: Fri Nov 3 2017
Return: Sun Nov 5 2017
Trip spans 3 days
$220
Select
Porter Airlines
MDW
→
YTZ
1h 37m
nonstop
YTZ
→
MDW
1h 50m
nonstop
Depart: Sat Sep 16 2017
Return: Wed Sep 27 2017
Trip spans 12 days
$376
Select
Delta
MDW
→
YVR
6h 53m
1 stop
YVR
→
MDW
8h 10m
1 stop
Depart: Fri Aug 18 2017
Return: Mon Aug 21 2017
Trip spans 4 days
$232
Select
Porter Airlines
MDW
→
YTZ
1h 45m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Sat Oct 7 2017
Return: Sun Oct 15 2017
Trip spans 9 days
$379
Select
Delta
MDW
→
YEG
5h 42m
1 stop
YEG
→
MDW
7h 19m
1 stop
Depart: Tue Aug 29 2017
Return: Sat Sep 2 2017
Trip spans 5 days
$235
Select
Porter Airlines
MDW
→
YTZ
1h 45m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Fri Oct 27 2017
Return: Tue Oct 31 2017
Trip spans 5 days
$388
Select
Delta
MDW
→
YVR
8h 39m
1 stop
YVR
→
MDW
7h 10m
1 stop
Depart: Thu Dec 28 2017
Return: Tue Jan 2 2018
Trip spans 6 days
$240
Select
Porter Airlines
MDW
→
YTZ
1h 37m
nonstop
YTZ
→
MDW
1h 50m
nonstop
Depart: Sat Sep 30 2017
Return: Tue Oct 3 2017
Trip spans 4 days
$409
Select
Delta
MDW
→
YYC
7h 58m
1 stop
YYC
→
MDW
5h 45m
1 stop
Depart: Sat Sep 9 2017
Return: Mon Sep 11 2017
Trip spans 3 days
$243
Select
Porter Airlines
MDW
→
YTZ
1h 40m
nonstop
YTZ
→
MDW
1h 45m
nonstop
Depart: Wed Oct 4 2017
Return: Sun Oct 8 2017
Trip spans 5 days
$409
Select
Delta
MDW
→
YYC
8h 02m
1 stop
YYC
→
MDW
5h 45m
1 stop
Depart: Thu Nov 9 2017
Return: Mon Nov 13 2017
Trip spans 5 days
$415
Select
Delta
MDW
→
YVR
6h 01m
1 stop
YVR
→
MDW
6h 20m
1 stop
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