Skyscanner home

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 airfare 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
DirectFrom AED 714
Ottawa
1+ stopsFrom AED 904
Calgary
DirectFrom AED 1,017
Montreal
1+ stopsFrom AED 1,021
See more destinations

Flying from Chicago to Canada

The things to know before you go.
Cheapest plane ticket foundAED 714
Cheapest month to flySeptember
Average flight time2 hrs, 15 mins
Places to go229
Most popular airlineUnited
Average flights per week1,303

Chicago to Canada flight deals

Looking for a cheap last-minute deal or the best roundtrip flight from Chicago to Canada? If you want to travel next month, roundtrip fares start from AED 764. Find the lowest prices on one-way and roundtrip flight tickets right here.
Toronto.AED 714 per passenger.Departing Sun, Sep 6, returning Wed, Sep 16.Round-trip flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Chicago O'Hare International on Sun, Sep 6, arriving in Toronto Island.Inbound direct flight with Porter Airlines departing from Toronto Island on Wed, Sep 16, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 714, select.
Ottawa.AED 904 per passenger.Departing Wed, Jul 8, returning Wed, Jul 8.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Wed, Jul 8, arriving in Ottawa International.Inbound indirect flight with Air Canada, departing from Ottawa International on Wed, Jul 8, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 904, select.
Calgary.AED 1,017 per passenger.Departing Mon, Sep 14, returning Fri, Oct 30.Round-trip flight with WestJet.Outbound direct flight with WestJet departing from Chicago O'Hare International on Mon, Sep 14, arriving in Calgary.Inbound direct flight with WestJet departing from Calgary on Fri, Oct 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,017, select.
Montreal.AED 1,021 per passenger.Departing Sat, Sep 5, returning Tue, Sep 8.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Chicago O'Hare International on Sat, Sep 5, arriving in Montreal St Hubert.Inbound indirect flight with Porter Airlines, departing from Montreal St Hubert on Tue, Sep 8, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,021, select.
Vancouver.AED 1,090 per passenger.Departing Mon, Aug 31, returning Mon, Sep 14.Round-trip flight with Frontier Airlines and WestJet.Outbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Mon, Aug 31, arriving in Vancouver International.Inbound indirect flight with WestJet, departing from Vancouver International on Mon, Sep 14, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,090, select.
Montreal.AED 1,126 per passenger.Departing Sat, Aug 15, returning Sat, Aug 22.Round-trip flight with Air Canada.Outbound direct flight with Air Canada departing from Chicago O'Hare International on Sat, Aug 15, arriving in Montreal Pierre Elliott Trudeau.Inbound direct flight with Air Canada departing from Montreal Pierre Elliott Trudeau on Sat, Aug 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,126, select.
Halifax.AED 1,203 per passenger.Departing Sat, Sep 12, returning Thu, Sep 17.Round-trip flight with Porter Airlines and WestJet.Outbound indirect flight with Porter Airlines, departing from Chicago O'Hare International on Sat, Sep 12, arriving in Halifax International.Inbound indirect flight with WestJet, departing from Halifax International on Thu, Sep 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,203, select.
Edmonton.AED 1,244 per passenger.Departing Tue, Sep 15, returning Tue, Sep 22.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Tue, Sep 15, arriving in Edmonton International.Inbound indirect flight with WestJet, departing from Edmonton International on Tue, Sep 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,244, select.
Winnipeg.AED 1,256 per passenger.Departing Tue, Sep 8, returning Mon, Sep 21.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Chicago O'Hare International on Tue, Sep 8, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Mon, Sep 21, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,256, select.
Saskatoon.AED 1,274 per passenger.Departing Wed, Aug 19, returning Sun, Aug 23.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Wed, Aug 19, arriving in Saskatoon.Inbound indirect flight with WestJet, departing from Saskatoon on Sun, Aug 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,274, select.
Quebec.AED 1,334 per passenger.Departing Fri, Jul 24, returning Fri, Jul 31.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Fri, Jul 24, arriving in Quebec.Inbound indirect flight with Air Canada, departing from Quebec on Fri, Jul 31, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,334, select.
Victoria.AED 1,434 per passenger.Departing Tue, Aug 18, returning Tue, Aug 25.Round-trip flight with Frontier Airlines and WestJet.Outbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Tue, Aug 18, arriving in Victoria International.Inbound indirect flight with WestJet, departing from Victoria International on Tue, Aug 25, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,434, select.
Regina.AED 1,455 per passenger.Departing Fri, Oct 9, returning Sun, Oct 11.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Fri, Oct 9, arriving in Regina.Inbound indirect flight with WestJet, departing from Regina on Sun, Oct 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,455, select.
Comox.AED 1,479 per passenger.Departing Tue, Sep 8, returning Tue, Sep 15.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Tue, Sep 8, arriving in Comox.Inbound indirect flight with WestJet, departing from Comox on Tue, Sep 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,479, select.
Kelowna.AED 1,485 per passenger.Departing Fri, Oct 16, returning Sun, Oct 18.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Fri, Oct 16, arriving in Kelowna.Inbound indirect flight with WestJet, departing from Kelowna on Sun, Oct 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,485, select.
Thunder Bay.AED 1,560 per passenger.Departing Fri, Jul 3, returning Thu, Jul 9.Round-trip flight with Porter Airlines and Flair Airlines.Outbound indirect flight with Porter Airlines, departing from Chicago Midway on Fri, Jul 3, arriving in Thunder Bay.Inbound indirect flight with Flair Airlines, departing from Thunder Bay on Thu, Jul 9, arriving in Chicago Midway.Price includes taxes and charges.From AED 1,560, select.
Show more deals

Flights from Chicago to Canada FAQs

The cheapest month to fly from Chicago to Canada is September. See if any of these flights in September 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 Island. You can buy a ticket to fly this route from AED 714.

Take a look at Chicago to Toronto Island flights.
The average flight time from Chicago to Canada is 2 hours and 17 minutes.
Looking at the year ahead, the cheapest airline flying to Canada from Chicago is Porter Airlines.

Explore flight ticket options today.

How to find cheap flights from Chicago to Canada

Looking for flight tickets from Chicago to Canada? Whether you're flying one-way or round-trip, here are a few tips on how to score the best price and make your flight journey as smooth as possible.

  • Simply hit "search." From United Airlines to international carriers like Emirates, we've compared flights from all major airlines and online travel agents to find the cheapest Chicago–Canada flights. And with us, there are no hidden fees – what you see is what you pay.
  • 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.
  • 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–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 points 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.

Book a ticket from Chicago to Canada with extra peace of mind

  • Find flexible flights from Chicago to Canada. Your airline might be offering flexible flight tickets from Chicago to Canada, which means you won't lose out if your flight has to be changed or canceled.
  • Add travel cost protection. Avoid travel pitfalls and research the possibility of adding insurance to your Chicago–Canada flight booking.

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 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 from your origin.


Canada hotels and car rentals

Did you know we can help you plan the rest of your trip from Chicago to Canada? Get exclusive deals and great rates for hotels and car rental in Canada.

More travel options

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.