Cheap Flights from Chicago Midway to Canada from $168

Looking for a cheap plane ticket from Chicago Midway to Canada? Whether you're looking for a direct flight, round-trip flight or one-way ticket, we've got you.

Toronto.$168 per passenger.Departing Wed, Jul 8, returning Tue, Jul 14.Round-trip flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Chicago Midway on Wed, Jul 8, arriving in Toronto Island.Inbound direct flight with Porter Airlines departing from Toronto Island on Tue, Jul 14, arriving in Chicago Midway.Price includes taxes and charges.From $168, select.

Montreal.$204 per passenger.Departing Wed, May 6, returning Wed, May 13.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Chicago Midway on Wed, May 6, arriving in Montreal Pierre Elliott Trudeau.Inbound indirect flight with Porter Airlines, departing from Montreal Pierre Elliott Trudeau on Wed, May 13, arriving in Chicago Midway.Price includes taxes and charges.From $204, select.

Calgary.$299 per passenger.Departing Sat, May 9, returning Sat, May 16.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago Midway on Sat, May 9, arriving in Calgary.Inbound indirect flight with Delta, departing from Calgary on Sat, May 16, arriving in Chicago Midway.Price includes taxes and charges.From $299, select.

Winnipeg.$342 per passenger.Departing Thu, Apr 23, returning Mon, Apr 27.Round-trip flight with Frontier Airlines and Flair Airlines.Outbound indirect flight with Frontier Airlines, departing from Chicago Midway on Thu, Apr 23, arriving in Winnipeg.Inbound indirect flight with Flair Airlines, departing from Winnipeg on Mon, Apr 27, arriving in Chicago Midway.Price includes taxes and charges.From $342, select.

Ottawa.$349 per passenger.Departing Sat, May 9, returning Sat, May 16.Round-trip flight with Porter Airlines and WestJet.Outbound indirect flight with Porter Airlines, departing from Chicago Midway on Sat, May 9, arriving in Ottawa International.Inbound indirect flight with WestJet, departing from Ottawa International on Sat, May 16, arriving in Chicago Midway.Price includes taxes and charges.From $349, select.

Vancouver.$382 per passenger.Departing Thu, Apr 23, returning Thu, Apr 30.Round-trip flight with Frontier Airlines and WestJet.Outbound indirect flight with Frontier Airlines, departing from Chicago Midway on Thu, Apr 23, arriving in Vancouver International.Inbound indirect flight with WestJet, departing from Vancouver International on Thu, Apr 30, arriving in Chicago Midway.Price includes taxes and charges.From $382, select.

Halifax.$395 per passenger.Departing Mon, Apr 27, returning Tue, May 5.Round-trip flight with Porter Airlines and Flair Airlines.Outbound indirect flight with Porter Airlines, departing from Chicago Midway on Mon, Apr 27, arriving in Halifax International.Inbound indirect flight with Flair Airlines, departing from Halifax International on Tue, May 5, arriving in Chicago Midway.Price includes taxes and charges.From $395, select.

Saskatoon.$409 per passenger.Departing Sat, May 9, returning Sat, May 16.Round-trip flight with Porter Airlines and WestJet.Outbound indirect flight with Porter Airlines, departing from Chicago Midway on Sat, May 9, arriving in Saskatoon.Inbound indirect flight with WestJet, departing from Saskatoon on Sat, May 16, arriving in Chicago Midway.Price includes taxes and charges.From $409, select.

See more deals

Flights from Chicago Midway Airport to Canada FAQs

What is the cheapest flight to Canada from Chicago Midway?

The cheapest flight from Chicago Midway to Canada costs $168.

Explore the different prices of flights from Chicago Midway to Canada and find the best option for you.

When is it the cheapest time to fly from Chicago Midway to Canada?

The cheapest month to fly from Chicago Midway to Canada is July. See if any of these flights in July suit you.

What is the cheapest Chicago Midway to Canada flight route?

We've taken a look at the year ahead using our flights calendar. The cheapest flight route from Chicago Midway to Canada is Chicago Midway to Toronto Island. You can buy a ticket to fly this route from $168.

Take a look at Chicago Midway to Toronto Island flights.

What is the cheapest airline that flies to Canada from Chicago Midway?

Looking at the year ahead, the cheapest airline flying to Canada from Chicago Midway is Porter Airlines.

Explore flight ticket options today.

Cheapest flights to Canada from Chicago Midway

How to find cheap flights from Chicago Midway to Canada

Looking for flight tickets from Chicago Midway 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 Midway–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 Midway-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 Midway 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 Midway 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 Midway to Canada? Make sure to tick "Direct flights only" when performing a search. If there are direct Chicago Midway–Canada flights available, these will appear in the results.
Find the cheapest Business Class flights from Chicago Midway to Canada. Check the difference in price of your plane ticket to Canada from Chicago Midway 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 Midway-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 Midway to Canada when out and about.

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

Find flexible flights from Chicago Midway to Canada. Your airline might be offering flexible flight tickets from Chicago Midway 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 Midway–Canada flight booking.

Combine your flight from Chicago Midway 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 Midway-to-Canada flight tickets with other routes using the Everywhere search

Not quite yet set on flying to Canada from Chicago Midway? 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 Midway to Canada? Get exclusive deals and great rates for hotels and car rentals in Canada too.