Cheapest plane ticket found	C$279
Cheapest month to fly	September
Average flight time	2 hrs, 18 mins
Places to go	228
Most popular airline	United
Average flights per week	5,668

Cheapest time to fly from Chicago to Canada

Looking for the lowest ticket prices to Canada from Chicago? We can help you pick the cheapest month to fly.

Jul.

from C$638

Aug.

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Chicago to Canada flight deals

Looking for a cheap last-minute deal or the best return flight from Chicago to Canada? If you want to travel next month, return fares start from C$325. Find the lowest prices on one-way and return flight tickets right here.

Toronto.C$279 per passenger.Departing Wed., Sep. 9, returning Mon., Sep. 21.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Wed., Sep. 9, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Mon., Sep. 21, arriving in Chicago Midway.Price includes taxes and charges.From C$279, select.

Calgary.C$327 per passenger.Departing Tue., Aug. 25, returning Tue., Sep. 1.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Tue., Aug. 25, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Tue., Sep. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$327, select.

Vancouver.C$367 per passenger.Departing Mon., Oct. 19, returning Fri., Oct. 23.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon., Oct. 19, arriving in Abbotsford.Inbound indirect flight with WestJet, departs from Abbotsford on Fri., Oct. 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$367, select.

Montreal.C$413 per passenger.Departing Tue., Aug. 18, returning Tue., Aug. 18.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Tue., Aug. 18, arriving in Montreal Pierre Elliott Trudeau.Inbound indirect flight with Air Canada, departs from Montreal Pierre Elliott Trudeau on Tue., Aug. 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$413, select.

Edmonton.C$424 per passenger.Departing Fri., Aug. 14, returning Thu., Aug. 27.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Fri., Aug. 14, arriving in Edmonton International.Inbound indirect flight with WestJet, departs from Edmonton International on Thu., Aug. 27, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$424, select.

Winnipeg.C$440 per passenger.Departing Sun., Oct. 11, returning Sun., Oct. 18.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Sun., Oct. 11, arriving in Winnipeg.Inbound indirect flight with WestJet, departs from Winnipeg on Sun., Oct. 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$440, select.

Saskatoon.C$470 per passenger.Departing Tue., Sep. 8, returning Tue., Sep. 15.Return flight with Porter Airlines and WestJet.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Tue., Sep. 8, arriving in Saskatoon.Inbound indirect flight with WestJet, departs from Saskatoon on Tue., Sep. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$470, select.

Regina.C$479 per passenger.Departing Tue., Aug. 18, returning Mon., Aug. 24.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Tue., Aug. 18, arriving in Regina.Inbound indirect flight with WestJet, departs from Regina on Mon., Aug. 24, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$479, select.

Comox.C$483 per passenger.Departing Tue., Sep. 8, returning Tue., Sep. 15.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Tue., Sep. 8, arriving in Comox.Inbound indirect flight with WestJet, departs from Comox on Tue., Sep. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$483, select.

Halifax.C$491 per passenger.Departing Fri., Sep. 18, returning Mon., Sep. 21.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Fri., Sep. 18, arriving in Halifax International.Inbound indirect flight with Porter Airlines, departs from Halifax International on Mon., Sep. 21, arriving in Chicago Midway.Price includes taxes and charges.From C$491, select.

Kelowna.C$495 per passenger.Departing Thu., Oct. 8, returning Sun., Oct. 11.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu., Oct. 8, arriving in Kelowna.Inbound indirect flight with WestJet, departs from Kelowna on Sun., Oct. 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$495, select.

Ottawa.C$502 per passenger.Departing Wed., Sep. 9, returning Wed., Sep. 16.Return flight with Porter Airlines and WestJet.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Wed., Sep. 9, arriving in Ottawa International.Inbound indirect flight with WestJet, departs from Ottawa International on Wed., Sep. 16, arriving in Chicago Midway.Price includes taxes and charges.From C$502, select.

Victoria.C$503 per passenger.Departing Thu., Sep. 24, returning Mon., Sep. 28.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu., Sep. 24, arriving in Victoria International.Inbound indirect flight with WestJet, departs from Victoria International on Mon., Sep. 28, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$503, select.

Prince George.C$522 per passenger.Departing Wed., Sep. 9, returning Wed., Sep. 16.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Wed., Sep. 9, arriving in Prince George.Inbound indirect flight with Air Canada, departs from Prince George on Wed., Sep. 16, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$522, select.

Cranbrook.C$537 per passenger.Departing Tue., Sep. 8, returning Tue., Sep. 15.Return flight with WestJet and Air Canada.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Tue., Sep. 8, arriving in Cranbrook.Inbound indirect flight with Air Canada, departs from Cranbrook on Tue., Sep. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$537, select.

Vancouver.C$540 per passenger.Departing Tue., Dec. 1, returning Tue., Dec. 8.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Chicago O'Hare International on Tue., Dec. 1, arriving in Vancouver International.Inbound direct flight with Air Canada departs from Vancouver International on Tue., Dec. 8, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$540, select.

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Flights from Chicago to Canada FAQs

What is the cheapest flight to Canada from Chicago?

The cheapest flight from Chicago to Canada costs C$279.

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

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

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

What is the cheapest Chicago to Canada flight route?

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 C$279.

Take a look at Chicago to Toronto Island flights.

How long is the flight from Chicago to Canada?

The average flight time from Chicago to Canada is 2 hours and 18 minutes.

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

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

Explore flight ticket options today.

Cheapest flights to Canada from Chicago

How to find cheap flights from Chicago to Canada

C$279 is currently the cheapest price for a return flight from Chicago to Canada.
You'll be travelling from Chicago into Toronto Island in Toronto with that fare.
A one-way ticket starts at C$119.
Happy to let the deals decide your next stop? Enter 'Canada' in the 'To' field to discover the lowest fares for different cities.
Canada has roughly 25 international airports, so you can choose from plenty of arrival options.
Expand your search by choosing 'Add nearby airports.' This will compare prices across the airports closest to both your departure and destination points, which could help you find a better deal.
Early booking can pay off. Fares are more likely to go up as your departure date gets closer, not drop.
Get notified when fares change by creating a Price Alert. Download the Skyscanner app to have updates sent straight to your phone.

Best time to fly from Chicago to Canada

Catch a flight from Chicago to Canada in September and you'll be travelling at one of the cheapest times of the year.
Tuesdays and Wednesdays are often the most affordable days to fly in general, with prices dipping during the quieter midweek period.
July, August and September are the most popular months to travel to Canada. July comes out on top, making it an ideal time to visit if you want everything open and buzzing.
Alternatively, skip the peak season rush by checking out flights in January, February and March. Out of these low season months, March is the quietest.

Flights from Chicago to Canada: what to expect

You can choose from Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW) when planning your Chicago departure.
Around ten airports throughout Canada can be reached on a nonstop flight from Chicago.
Roughly 282 direct flights connect Chicago with cities across Canada every week.
The main airlines flying this route are:
When it comes to the most popular routes from Chicago to Canada, Toronto, Montreal and Vancouver sit high on the travel wishlist.
Toronto is the quickest destination to reach at around 1 hour 40 minutes, while Vancouver has the longest flight time at roughly 4 hours 35 minutes.
Across all routes, the average journey takes around 2 hours 55 minutes.

Popular places to visit in Canada

Toronto

Located in Ontario, this city is a popular destination for Chicago to Canada flights. CN Tower, Royal Ontario Museum and Toronto Islands are must-sees for first-time visitors.
There are plenty of flight deals to Toronto's busiest airport, Toronto Pearson International Airport (YYZ). Toronto Island Airport (YTZ) and John C. Munro Hamilton Airport (YHM) give you even more flexibility.
Ready to lock in your perfect base? Browse the lineup of hotels in Toronto.

Vancouver

The biggest highlights in this British Columbia city include Stanley Park Seawall, Stanley Park and Downtown Vancouver.
When deciding where to land, your options include Vancouver International Airport (YVR), Vancouver Coal Harbour Airport (CXH) and Abbotsford Airport (YXX).
After locking in your airfare, you can move on to finding the right stay among the hotels in Vancouver.

Montreal

Well-known attractions to tick off while you're in this part of Quebec include Notre-Dame Basilica of Montreal, Montreal International Jazz Festival and Cirque du Soleil.
You can touch down at Montreal Pierre Elliott Trudeau Airport (YUL), Montreal St Hubert Airport (YHU) or Montreal Mirabel Airport (YMX), depending on what fits your route best.
From brief visits to extended stays, hotels in Montreal cater to all types of budgets and travel styles.

Visiting Canada for the first time? Here's what you need to know

Entry rules can vary, so check whether you'll need a visa or any other type of documentation before you travel. Your airline, travel agent or the local consulate or embassy should have the most up-to-date information.
The Canadian dollar (CAD) is the main currency.
Ottawa is the capital of Canada, which has a population of roughly 41 million.
Standard time zones across this destination vary, from UTC-8 to UTC-3.
Choose the season that matches how you like to explore, whether that's cooler, hotter or somewhere in between. July is one of the warmest months in Canada.
Conditions are often coolest around February.
October is usually the rainiest month, while February is the driest.
Headline events on the local calendar include Canada Day, Calgary Stampede and the Toronto International Film Festival. Line up your Chicago to Canada flight around moments like these to experience something beyond the everyday.

Complete your trip with hotels and a car rental

With your cheap flight from Chicago to Canada booked, it's time to plan what comes next. Discover the best prices and exclusive rates for hotels in Canada. You can also check out car rental options in Canada and compare offers from top providers in seconds.

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.