Cheap flights from Chicago to Canada from $195

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.

See more destinations

Flying from Chicago to Canada

The things to know before you go.

Cheapest plane ticket found	$195
Cheapest month to fly	May
Average flight time	2 hrs, 19 mins
Places to go	225
Most popular airline	United
Average flights per week	1,441

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.

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Chicago to Canada flight deals

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

Montreal.$195 per passenger.Departing Fri, May 1, returning Wed, May 6.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Chicago Midway on Fri, May 1, arriving in Montreal Pierre Elliott Trudeau.Inbound indirect flight with Porter Airlines, departing from Montreal Pierre Elliott Trudeau on Wed, May 6, arriving in Chicago Midway.Price includes taxes and charges.From $195, select.

Calgary.$207 per passenger.Departing Wed, May 27, returning Sat, May 30.Round-trip flight with WestJet.Outbound direct flight with WestJet departing from Chicago O'Hare International on Wed, May 27, arriving in Calgary.Inbound direct flight with WestJet departing from Calgary on Sat, May 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From $207, select.

Toronto.$211 per passenger.Departing Wed, Apr 29, returning Sat, May 2.Round-trip flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Chicago Midway on Wed, Apr 29, arriving in Toronto Island.Inbound direct flight with Porter Airlines departing from Toronto Island on Sat, May 2, arriving in Chicago Midway.Price includes taxes and charges.From $211, select.

Vancouver.$235 per passenger.Departing Thu, May 28, returning Tue, Jun 2.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Thu, May 28, arriving in Abbotsford.Inbound indirect flight with WestJet, departing from Abbotsford on Tue, Jun 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From $235, select.

Edmonton.$249 per passenger.Departing Sun, May 31, returning Wed, Jun 3.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Sun, May 31, arriving in Edmonton International.Inbound indirect flight with WestJet, departing from Edmonton International on Wed, Jun 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From $249, select.

Saskatoon.$260 per passenger.Departing Mon, Apr 27, returning Sun, May 3.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Mon, Apr 27, arriving in Saskatoon.Inbound indirect flight with WestJet, departing from Saskatoon on Sun, May 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From $260, select.

Winnipeg.$267 per passenger.Departing Sat, May 2, returning Sat, May 9.Round-trip flight with Frontier Airlines and WestJet.Outbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Sat, May 2, arriving in Winnipeg.Inbound indirect flight with WestJet, departing from Winnipeg on Sat, May 9, arriving in Chicago O'Hare International.Price includes taxes and charges.From $267, select.

Victoria.$268 per passenger.Departing Sun, Apr 26, returning Sun, May 3.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Sun, Apr 26, arriving in Victoria International.Inbound indirect flight with WestJet, departing from Victoria International on Sun, May 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From $268, select.

See more deals

Flights from Chicago to Canada FAQs

What is the cheapest flight to Canada from Chicago?

The cheapest flight from Chicago to Canada costs $195.

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 May. See if any of these flights in May 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 Montreal Pierre Elliott Trudeau. You can buy a ticket to fly this route from $195.

Take a look at Chicago to Montreal Pierre Elliott Trudeau flights.

How long is the flight from Chicago to Canada?

The average flight time from Chicago to Canada is 2 hours and 13 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 Porter Airlines flight ticket options today.

If this airline doesn't suit you, the second cheapest airline is WestJet.

Cheapest flights to Canada from Chicago

How to find cheap flights from Chicago to Canada

Looking for affordable flights from Chicago to Canada? We make it simple. Use Skyscanner to compare major airlines and online travel agents, ensuring no hidden fees surprise you later. October is the cheapest month to fly, perfect for budgeting travel enthusiasts. With over 4,500 flights on average each week and an average journey duration of 2 hours and 15 minutes, you have plenty of options. Use our Whole Month view to spot cost-effective dates quickly and set up Price Alerts to keep up with fare changes. Exploring nearby airports may add potential savings, and filtering for direct routes shows faster options. Consider flexible tickets or travel insurance for added peace of mind if plans change.

Other routes from the United States to Canada

At Skyscanner, we offer a variety of routes from the United States to Canada, making your travel plans convenient. From Boston, you can book direct flights to destinations such as Toronto or Montreal. If you are traveling from Seattle, you have options such as Vancouver or Calgary. In Houston, travelers can find direct trips to Toronto and Montreal. Those departing from Miami can explore options to fly into Toronto. Skyscanner allows you to compare these routes easily, ensuring that you find the best option for your travel needs. Start your journey with us today.

Canada destinations you can fly to from Chicago

From Chicago, it's practical to fly to Vancouver, Calgary, Toronto, and Montreal. In Calgary, attend the Calgary Stampede or visit Heritage Park Historical Village. Toronto offers the CN Tower and St. Lawrence Market as highlights. Montreal's Old Montreal and Mont-Royal Park are notable attractions. In Montreal, expect French cultural influences. Each city has distinct points of interest: Vancouver is known for its natural scenery and active lifestyle, Calgary for its cultural events, Toronto for its cityscape and diverse neighborhoods, and Montreal for its blend of history and modernity. Plan for varied outdoor and cultural experiences across these destinations.

The cheapest city in Canada to catch a flight to

If you are flying from Chicago, Vancouver is the cheapest city in Canada to travel to. Once you arrive, consider visiting Stanley Park for outdoor activities or explore the historic Gastown with its unique architecture. You can also visit Granville Island Public Market for fresh produce and unique crafts. Vancouver offers these attractions alongside affordable travel options, making it an appealing destination for budget-conscious travelers.

The weather in Canada

Canada's weather varies widely, affecting what you should pack for your trip. The northern regions experience extremely cold temperatures, especially in winter, while the south has milder, temperate conditions. Visiting in spring is more economical, with moderate temperatures between 50°F and 68°F. Summer is perfect for outdoor activities, although it is often hot and humid. Autumn offers cooler weather and fewer crowds, whereas winter invites you skiing, especially in British Columbia and Quebec. Stay informed about potential severe weather events, such as storms and flooding, particularly in Ontario and Quebec. Always plan for shifting conditions by dressing in layers.

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.