C$273 Cheap Flights from Chicago to Canada

Return selected

origin

Enter the city you're flying from, or choose from the options below

Include nearby airports

selected

destination

. Enter your destination, or choose from the options below

Include nearby airports

selected

Travellers and cabin class, 1 Adult, Economy

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

Destinations Route info Cheapest month Flight deals FAQs Tips and advice

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	C$273
Cheapest month to fly	October
Average flight time	2 hrs, 16 mins
Places to go	229
Most popular airline	United
Average flights per week	1,403

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$275. Find the lowest prices on one-way and return flight tickets right here.

Toronto.C$273 per passenger.Departing Thu., Oct. 15, returning Sun., Nov. 1.Return flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Chicago Midway on Thu., Oct. 15, arriving in Toronto Island.Inbound direct flight with Porter Airlines departs from Toronto Island on Sun., Nov. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$273, select.

Montreal.C$312 per passenger.Departing Fri., Nov. 13, returning Fri., Nov. 13.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri., Nov. 13, arriving in Montreal Pierre Elliott Trudeau.Inbound indirect flight with Air Canada, departs from Montreal Pierre Elliott Trudeau on Fri., Nov. 13, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$312, select.

Cranbrook.C$350 per passenger.Departing Sun., Oct. 18, returning Fri., Oct. 23.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Sun., Oct. 18, arriving in Cranbrook.Inbound indirect flight with WestJet, departs from Cranbrook on Fri., Oct. 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$350, select.

Calgary.C$357 per passenger.Departing Fri., Oct. 16, returning Fri., Oct. 23.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri., Oct. 16, arriving in Calgary.Inbound indirect flight with Air Canada, departs from Calgary on Fri., Oct. 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$357, select.

Saskatoon.C$360 per passenger.Departing Thu., Oct. 15, returning Thu., Oct. 22.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu., Oct. 15, arriving in Saskatoon.Inbound indirect flight with WestJet, departs from Saskatoon on Thu., Oct. 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$360, select.

Victoria.C$364 per passenger.Departing Fri., Oct. 16, returning Thu., Oct. 22.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Fri., Oct. 16, arriving in Victoria International.Inbound indirect flight with WestJet, departs from Victoria International on Thu., Oct. 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$364, select.

Nanaimo.C$368 per passenger.Departing Tue., Oct. 6, returning Mon., Oct. 12.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Tue., Oct. 6, arriving in Nanaimo.Inbound indirect flight with WestJet, departs from Nanaimo on Mon., Oct. 12, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$368, select.

Kelowna.C$378 per passenger.Departing Fri., Sep. 25, returning Sat., Oct. 3.Return flight with WestJet and Air Canada.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Fri., Sep. 25, arriving in Kelowna.Inbound indirect flight with Air Canada, departs from Kelowna on Sat., Oct. 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$378, select.

Vancouver.C$392 per passenger.Departing Thu., Oct. 15, returning Thu., Oct. 22.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu., Oct. 15, arriving in Abbotsford.Inbound indirect flight with WestJet, departs from Abbotsford on Thu., Oct. 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$392, select.

Edmonton.C$405 per passenger.Departing Thu., Oct. 8, returning Mon., Oct. 12.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu., Oct. 8, arriving in Edmonton International.Inbound indirect flight with WestJet, departs from Edmonton International on Mon., Oct. 12, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$405, select.

Whitehorse.C$408 per passenger.Departing Fri., Oct. 16, returning Thu., Oct. 22.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri., Oct. 16, arriving in Whitehorse.Inbound indirect flight with Air Canada, departs from Whitehorse on Thu., Oct. 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$408, select.

Kamloops.C$420 per passenger.Departing Sat., Oct. 17, returning Sat., Oct. 24.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sat., Oct. 17, arriving in Kamloops.Inbound indirect flight with Air Canada, departs from Kamloops on Sat., Oct. 24, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$420, select.

Regina.C$427 per passenger.Departing Fri., Oct. 16, returning Fri., Oct. 23.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Fri., Oct. 16, arriving in Regina.Inbound indirect flight with WestJet, departs from Regina on Fri., Oct. 23, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$427, select.

Winnipeg.C$431 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$431, select.

Grande Prairie.C$434 per passenger.Departing Mon., Sep. 28, returning Mon., Oct. 5.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon., Sep. 28, arriving in Grande Prairie.Inbound indirect flight with WestJet, departs from Grande Prairie on Mon., Oct. 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$434, select.

Terrace.C$447 per passenger.Departing Mon., Nov. 2, returning Tue., Nov. 10.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon., Nov. 2, arriving in Terrace.Inbound indirect flight with Air Canada, departs from Terrace on Tue., Nov. 10, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$447, select.

Show more deals

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 C$273.

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 C$273.

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

C$273 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$105.
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 October 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.