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Cheap Chicago to Canada flights

Compare flights from Chicago to Canada

Find the cheapest month or even day of the year to fly

Book the best fare with no fees

Where in Canada would you like to go?

There are lots of destinations to choose from when you're planning your trip from Chicago to Canada.
Toronto
1+ stopsFrom £174
Toronto
DirectFrom £197
Vancouver
1+ stopsFrom £215
Calgary
DirectFrom £226
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Flying from Chicago to Canada

The things to know before you go.
Cheapest flight ticket found£174
Cheapest month to flyMay
Average flight time2 hrs, 16 mins
Places to go233
Most popular airlineUnited
Average flights per week1,000

Cheapest time to fly from Chicago to Canada

Looking for the cheapest ticket prices to Canada from Chicago? We can help you pick the cheapest month to fly.
Apr
from £506
May
from £215
Jun
from £197
Jul
from £226
Aug
from £231
Sep
from £246
Oct
from £247
Nov
Find prices
Dec
from £420
Jan
Find prices
Feb
Find prices
Mar
Find prices

Chicago to Canada flight deals

Looking for a cheap flight ticket from Chicago to Canada? Whether you're looking for a direct flight, return flight or one way ticket we've got you.
Toronto.£174 per passenger.Departing Thu, 30 May, returning Sun, 2 Jun.Return flight with Frontier Airlines and Porter Airlines (Canada) Ltd.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 30 May, arriving in Toronto Pearson International.Inbound indirect flight with Porter Airlines (Canada) Ltd, departs from Toronto Island on Sun, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £174, select.
Toronto.£197 per passenger.Departing Tue, 4 Jun, returning Mon, 10 Jun.Return flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departs from Chicago Midway on Tue, 4 Jun, arriving in Toronto Island.Inbound direct flight with Porter Airlines (Canada) Ltd departs from Toronto Island on Mon, 10 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £197, select.
Vancouver.£215 per passenger.Departing Tue, 14 May, returning Sat, 18 May.Return flight with Spirit Airlines and Flair Airlines.Outbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 14 May, arriving in Vancouver International.Inbound indirect flight with Flair Airlines, departs from Vancouver International on Sat, 18 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From £215, select.
Calgary.£226 per passenger.Departing Fri, 26 Jul, returning Tue, 30 Jul.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Fri, 26 Jul, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Tue, 30 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From £226, select.
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Flights from Chicago to Canada FAQs

The cheapest month to fly from Chicago to Canada is May. See if any of these flights in May suit you.
We've taken a look at the year ahead using our flights calendar. The cheapest flight route from Chicago to Canada is Chicago to Toronto Pearson International. You can buy a ticket to fly this route from £174.

Take a look at Chicago to Toronto Pearson International flights.
The average flight time from Chicago to Canada is 2 hours and 10 minutes.
Looking at the year ahead, the cheapest airline flying to Canada from Chicago is Frontier Airlines.

Explore Frontier Airlines flight ticket options today. 

If this airline doesn't suit you, the second cheapest airline is Porter Airlines (Canada) Ltd.

How to find cheap flights from Chicago to Canada

Looking for flight tickets from Chicago to Canada? Round-trip tickets start from £174 and one-way flights from Chicago to Canada start from £53

Here are some tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit "search." From American Airlines to international carriers like Emirates, we've compared flights from all major airlines and online travel agents to find the cheapest Chicago to Canada flights. And with us, there are no hidden fees – what you see is what you pay.
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  • Compare cheap Chicago to Canada flight deals from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys. Flight tickets to Canada start from £53 one-way.
  • Flex your dates to secure the best fares for your Chicago to Canada ticket. If your travel dates are flexible, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly from Chicago to Canada.
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  • Set up a Price Alert. We price-check with over 1,000 travel companies so you don't have to. You can easily track the price of your airline tickets from Chicago to Canada by creating an alert. Whenever prices go up or down, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Look for direct flights. Only interested in direct flights from Chicago to Canada? Make sure to tick "Direct flights only" when performing a search. If there are direct Chicago to Canada flights available, these will appear in the results.
  • Find the cheapest Business Class flights from Chicago to Canada. Check the difference in price of your plane ticket to Canada from Chicago when traveling in Economy, Premium Economy, Business or First Class. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Chicago to Canada flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure and destination point and could help you save money.
  • Search for flights on the go. To get the best flight booking experience on the go, download our app and search for cheap flight tickets from Chicago to Canada when out and about.

Combine your flight from Chicago to Canada with hotels and car rental

Once you've secured your plane ticket, we'll also help you discover the best prices and exclusive rates for hotels in Canada or close by. Lastly, compare hundreds of car rental companies at once so that you get the best car rental deals for your trip.

Compare Chicago to Canada flight tickets with other routes using the everywhere search

Not quite yet set on flying to Canada from Chicago? You can easily browse other destinations by searching flights to "Everywhere" – this will allow you to find the cheapest place to travel to.


Prices shown on this page are estimated lowest prices only. Found in the last 45 days.