Flights from Chicago to Canada

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.

Cheap Chicago - Canada flight offers

Find cheap flight tickets and last-minute flight deals from Chicago to Canada

Porter Airlines
Mon, 06-15 (CHI) Chicago -> (YTO) Toronto
Direct
Porter Airlines
Thu, 06-25 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 4 days ago
from Can$245
United
Mon, 06-15 (CHI) Chicago -> (YTO) Toronto
Direct
United
Fri, 06-19 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 14 days ago
from Can$339
Porter Airlines
Fri, 06-26 (CHI) Chicago -> (YTO) Toronto
Direct
Porter Airlines
Wed, 07-01 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 10 days ago
from Can$383
Porter Airlines
Fri, 07-10 (CHI) Chicago -> (YTO) Toronto
Direct
Porter Airlines
Fri, 07-17 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 10 days ago
from Can$383
Air Canada
Sat, 06-06 (CHI) Chicago -> (YTO) Toronto
Direct
Air Canada
Sun, 06-07 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 8 days ago
from Can$392
Air Canada
Fri, 06-05 (CHI) Chicago -> (YUL) Montreal
Direct
Air Canada
Sun, 06-07 (YUL) Montreal -> (CHI) Chicago
Direct
Price found 12 days ago
from Can$484
Porter Airlines
Thu, 10-01 (CHI) Chicago -> (YUL) Montreal
Direct
Porter Airlines
Sat, 10-31 (YUL) Montreal -> (CHI) Chicago
Direct
Price found 15 days ago
from Can$498
United
Mon, 06-22 (CHI) Chicago -> (YVR) Vancouver
Direct
United
Fri, 06-26 (YVR) Vancouver -> (CHI) Chicago
Direct
Price found 2 days ago
from Can$520
United
Thu, 06-11 (CHI) Chicago -> (YTO) Toronto
Direct
Price found Yesterday
from Can$185
DELTA
Fri, 08-28 (CHI) Chicago -> (YUL) Montreal
Direct
Price found 15 days ago
from Can$211
Air Canada
Sat, 06-20 (CHI) Chicago -> (YKF) Kitchener Lake
Price found Yesterday
from Can$233
United
Fri, 04-09 (CHI) Chicago -> (YMQ) Montreal
Direct
Price found 14 days ago
from Can$257
Air Canada
Sun, 06-21 (CHI) Chicago -> (YKF) Kitchener Lake
Price found Yesterday
from Can$387
United
Sat, 04-10 (CHI) Chicago -> (YMQ) Montreal
Direct
Price found 15 days ago
from Can$600
Porter Airlines
Mon, 06-15 (CHI) Chicago -> (YTO) Toronto
Direct
Porter Airlines
Thu, 06-25 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 4 days ago
from Can$245
United
Mon, 06-15 (CHI) Chicago -> (YTO) Toronto
Direct
United
Fri, 06-19 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 14 days ago
from Can$339
Porter Airlines
Fri, 06-26 (CHI) Chicago -> (YTO) Toronto
Direct
Porter Airlines
Wed, 07-01 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 10 days ago
from Can$383
Porter Airlines
Fri, 07-10 (CHI) Chicago -> (YTO) Toronto
Direct
Porter Airlines
Fri, 07-17 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 10 days ago
from Can$383
Air Canada
Sat, 06-06 (CHI) Chicago -> (YTO) Toronto
Direct
Air Canada
Sun, 06-07 (YTO) Toronto -> (CHI) Chicago
Direct
Price found 8 days ago
from Can$392
Air Canada
Fri, 06-05 (CHI) Chicago -> (YUL) Montreal
Direct
Air Canada
Sun, 06-07 (YUL) Montreal -> (CHI) Chicago
Direct
Price found 12 days ago
from Can$484
Porter Airlines
Thu, 10-01 (CHI) Chicago -> (YUL) Montreal
Direct
Porter Airlines
Sat, 10-31 (YUL) Montreal -> (CHI) Chicago
Direct
Price found 15 days ago
from Can$498
United
Mon, 06-22 (CHI) Chicago -> (YVR) Vancouver
Direct
United
Fri, 06-26 (YVR) Vancouver -> (CHI) Chicago
Direct
Price found 2 days ago
from Can$520
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

Top airlines on the route Chicago - Canada

Airlines providing flights to Canada from Chicago

American Airlines
American Airlines
Air Canada
Air Canada
Alaska Airlines
Alaska Airlines
DELTA
DELTA
Porter Airlines
Porter Airlines
Air Transat
Air Transat
United
United

Flights to Canada in just a few clicks

Book your cheap flights from Chicago to Canada with Jetcost in seconds. Take advantage of deals from the best airlines and best online travel agencies. Simply enter your travel details and compare flight prices from Chicago to Canada. Find cheap low-cost flights in one click.

Don't miss the chance to find the right ticket for you among thousands of flight offers from Chicago to Canada. With Jetcost you will find the best flight at the lowest price . Book your cheap flight now from Chicagoto Canada with Jetcost.

The best flights from Chicago to Canada at the best price

Every day our database records offers from over 600 specialized agencies and airlines from all over the world, so that you can get the best price for your next flight from Chicago to Canada. Don't miss the right opportunity for you and filter your search according to your preferences and needs: choose the company, the agency, whether to stop over or look for direct flights only. You can filter and modify your search at any time: choose the number of passengers, the class you want to travel in and the dates of your trip and Jetcost will do the rest in seconds. Choose the right ticket for you from Chicago to Canada and save even more by flying on the cheapest days.