Cheap flights from Chicago to Canada from $196

Compare flights from Chicago to Canada

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Flying from Chicago to Canada

The things to know before you go.

Cheapest plane ticket found	$196
Cheapest month to fly	October
Average flight time	2 hrs, 18 mins
Places to go	229
Most popular airline	United
Average flights per week	1,309

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 $196. Find the lowest prices on one-way and roundtrip flight tickets right here.

Toronto.$196 per passenger.Departing Tue, Oct 6, returning Sun, Oct 11.Round-trip flight with Porter Airlines.Outbound direct flight with Porter Airlines departing from Chicago Midway on Tue, Oct 6, arriving in Toronto Island.Inbound direct flight with Porter Airlines departing from Toronto Island on Sun, Oct 11, arriving in Chicago Midway.Price includes taxes and charges.From $196, select.

Montreal.$225 per passenger.Departing Fri, Nov 13, returning Fri, Nov 13.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Fri, Nov 13, arriving in Montreal Pierre Elliott Trudeau.Inbound indirect flight with Air Canada, departing from Montreal Pierre Elliott Trudeau on Fri, Nov 13, arriving in Chicago O'Hare International.Price includes taxes and charges.From $225, select.

Kelowna.$241 per passenger.Departing Fri, Sep 18, returning Tue, Sep 22.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Fri, Sep 18, arriving in Kelowna.Inbound indirect flight with WestJet, departing from Kelowna on Tue, Sep 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From $241, select.

Victoria.$251 per passenger.Departing Fri, Oct 16, returning Fri, Oct 23.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Fri, Oct 16, arriving in Victoria International.Inbound indirect flight with WestJet, departing from Victoria International on Fri, Oct 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From $251, select.

Cranbrook.$253 per passenger.Departing Sun, Oct 18, returning Fri, Oct 23.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Sun, Oct 18, arriving in Cranbrook.Inbound indirect flight with WestJet, departing from Cranbrook on Fri, Oct 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From $253, select.

Saskatoon.$255 per passenger.Departing Thu, Oct 15, returning Thu, Oct 22.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Thu, Oct 15, arriving in Saskatoon.Inbound indirect flight with WestJet, departing from Saskatoon on Thu, Oct 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From $255, select.

Vancouver.$260 per passenger.Departing Thu, Oct 8, returning Thu, Oct 15.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Thu, Oct 8, arriving in Abbotsford.Inbound indirect flight with WestJet, departing from Abbotsford on Thu, Oct 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From $260, select.

Calgary.$264 per passenger.Departing Fri, Oct 16, returning Fri, Oct 23.Round-trip flight with American Airlines.Outbound direct flight with American Airlines departing from Chicago O'Hare International on Fri, Oct 16, arriving in Calgary.Inbound direct flight with American Airlines departing from Calgary on Fri, Oct 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From $264, select.

Regina.$270 per passenger.Departing Fri, Oct 16, returning Fri, Oct 23.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Fri, Oct 16, arriving in Regina.Inbound indirect flight with WestJet, departing from Regina on Fri, Oct 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From $270, select.

Nanaimo.$282 per passenger.Departing Sun, Oct 11, returning Sun, Oct 18.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Sun, Oct 11, arriving in Nanaimo.Inbound indirect flight with WestJet, departing from Nanaimo on Sun, Oct 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $282, select.

Edmonton.$283 per passenger.Departing Thu, Oct 15, returning Sun, Oct 18.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Thu, Oct 15, arriving in Edmonton International.Inbound indirect flight with WestJet, departing from Edmonton International on Sun, Oct 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $283, select.

Kamloops.$304 per passenger.Departing Sat, Oct 17, returning Sat, Oct 24.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Sat, Oct 17, arriving in Kamloops.Inbound indirect flight with Air Canada, departing from Kamloops on Sat, Oct 24, arriving in Chicago O'Hare International.Price includes taxes and charges.From $304, select.

Whitehorse.$311 per passenger.Departing Sat, Nov 14, returning Tue, Nov 17.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Sat, Nov 14, arriving in Whitehorse.Inbound indirect flight with Air Canada, departing from Whitehorse on Tue, Nov 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From $311, select.

Winnipeg.$312 per passenger.Departing Sun, Oct 11, returning Sun, Oct 18.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Sun, Oct 11, arriving in Winnipeg.Inbound indirect flight with WestJet, departing from Winnipeg on Sun, Oct 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $312, select.

Comox.$314 per passenger.Departing Sun, Oct 11, returning Sun, Oct 18.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Sun, Oct 11, arriving in Comox.Inbound indirect flight with Air Canada, departing from Comox on Sun, Oct 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $314, select.

Grande Prairie.$314 per passenger.Departing Mon, Sep 28, returning Mon, Oct 5.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Chicago O'Hare International on Mon, Sep 28, arriving in Grande Prairie.Inbound indirect flight with WestJet, departing from Grande Prairie on Mon, Oct 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From $314, select.

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Airlines with direct flights from Chicago to Canada

Alternative Chicago to Canada routes

Compare flight prices from airports across Canada. If you're flexible, you might find a cheaper flight or a faster route from a different airport.

Flights from Chicago to Canada FAQs

What is the cheapest flight to Canada from Chicago?

The cheapest flight from Chicago to Canada costs $196.

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 October. See if any of these flights in October 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 $196.

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 19 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

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.