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C$ 92 Find cheap flights from Chicago to Canada

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Canada departing on 31/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags

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Best Canada Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Toronto
Toronto1 stopC$ 316
Ottawa
Ottawa1 stopC$ 443
Kelowna
Kelowna2 stopsC$ 498
Québec City
Québec City1 stopC$ 471

Good to know

Low season

January

High season

July
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 0% lower on average.

FAQs - booking Canada flights

  • Do I need a visa to take flights from Chicago to Canada?

    American citizens won't need to secure visas to fly to Canada, as long as they don't plan to be in the country for more than 180 days. They will, however, need to have valid passports to make their way into Canada once they arrive after taking a flight from Chicago.

  • Where might I have to make stops while flying from Chicago to Canada?

    In a perfect world, you won't need to be concerned about making any stops while flying from Chicago to Canada. But if you do have to make them, you can expect layovers to take place at airports like Detroit Metropolitan Wayne County Airport (DTW), where you can stock up on Detroit Lions gear at the Michigan Sports store.

  • Which airlines offer first-class flights from Chicago to Canada?

    Some airlines that offer flights from Chicago to Canada, such as Porter Airlines, don't have first-class sections. But the majority of them, including Air Canada, American Airlines, and United Airlines, can set you up with first-class tickets when you want to book them for trips to Canada.

  • How can I help make flights from Chicago to Canada sustainable?

    You can make flights from Chicago to Canada sustainable by packing light and choosing the right airline to fly with. Look for an airline like Air Canada that has committed to reducing its carbon emissions dramatically by 2050 to make your flight as sustainable as possible.

  • How does KAYAK find such low prices on flights from Chicago to Canada?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Canada.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Canada?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Canada from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Canada?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Canada with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Canada?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Canada from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Canada

  • Morning departure is around 15% more expensive than an evening flight, on average*.
  • Those looking to catch flights from Chicago to Canada can choose between two airports in the Chicago area. Chicago O'Hare International Airport (ORD) is the main airport and the one most people pick when traveling to Canada, but Chicago Midway International Airport (MDW) is another good option to consider.
  • You will need to consider which Canadian airport you want to use as a destination. Toronto Pearson International Airport (YYZ) is the largest airport in the country, but even if you're planning to fly to Toronto, it won't be the automatic choice. Billy Bishop Toronto City Airport (YTZ ) is another fantastic option. You'll also be able to access other parts of Canada by booking flights to Montréal-Pierre Elliott Trudeau International Airport (YUL), Calgary International Airport (YYC), and Halifax Stanfield International Airport (YHZ).
  • There are a few U.S. airlines, such as American Airlines and United Airlines, that offer flights from Chicago to Canada. But your best bet when flying to Canada might be to select one of the Canadian airlines, since they tend to provide more flight options. Air Canada, WestJet , and Porter Airlines can all provide a wealth of options to fit your travel plans.
  • You'll want to shop around for nonstop flights from Chicago to Canada as opposed to settling for flights that make stops. Air Canada has direct flights that can get you to Toronto Pearson International Airport in around 1 hour and 33 minutes. Porter Airlines has direct flights that can take you to Billy Bishop Toronto City Airport in just about 1 hour and 37 minutes.
  • Aim to arrive at least 2 hours early for flights from Chicago to Canada. Upon your arrival, you can relax in one of the lounges found in the Chicago airports. Chicago O'Hare International Airport has options like the Admirals Club available to American Airlines passengers, while Chicago Midway International Airport has Club MDW that is open to all passengers for a small fee.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Flights from Chicago to Canada: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from Chicago to Canada 
Verified travelerFlew with Porter AirlinesMDW-YTZSep 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
JohannesFlew with Air CanadaORD-YYZSep 2024
Avoid the red eye flight if you get older/retire.
MarcFlew with United AirlinesORD-YOWMar 2024
United's fleet of smaller aircraft on this route is very comfortable.
Verified travelerFlew with United AirlinesORD-YOWJan 2024
I always expect issues with United but there doesn't seem to be another airline to use. Advice: Give yourself and extra day to get anywhere - don't be in a hurry to get home either.

Top 3 airlines serving from Chicago to Canada

Need help choosing which airline to fly with from Chicago to Canada? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
Porter AirlinesOverall score based on 300 reviews
8.6Crew
8.1Boarding
6.9Entertainment
8.0Comfort
7.7Food
Airline reviews

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

10.0 ExcellentMatthew, Oct 2024YYJ - YYZ
Read more Porter Airlines reviews

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Service was amazing, and the plane was comfortable even for this long haul. But they could have more movies selections. But they were still a lot to choose from.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

United needs to figure out its Economy PLUS standards; its better than economy but that's not saying much. It seems like United stripped away all the basics for an international flight (such as In Seat entertainment) and repackaged some of them as plus. Would not fly United internationally again.

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Flight was delayed due to weather and clogged toilet. Had to deplane. Flight was 3 hours delayed. Crew was awesome and offered water and snacks.

Didn't make it dir to delays - no support from United staff

Horrible! I paid for a straight flight from Chicago to London. A week before trip it changed and now I had a connecting flight. Our flight was delayed an hour and a half because our flight crew was still flying in from CA. Forty passengers ran from one plane to the next. The next United Airlines flight was delayed two to three hours because of mechanical difficulties. They had to ready another plane which took time. I missed my scheduled excursion in London. 😢

My flight was delayed for a whole day, so I lost a day of my vacation.

United cancelled the flight after a 2 hour delay. The only choice was a 24 hour delay which was then 3 hours delayed.

The mid flight snack could have been more substantial than tiny bag of pretzels.

Flight was over an hour late departing and when we got to Montreal there was no gate and so we had to wait on the tarmac for over an hour!!!!!

No complaints l will always do Air Canada once they are flying where I want to go

Same problem with the entertainment controls being on top of the armrests than on the previous flight, also a Boeing 737 series.

2 weeks before the flight we have got a pilot strike notice. Luckily it didn’t happen but we had to buy a travel insurance. It was wasted.

No service in the main cabin whatsoever! I finally ask for water and was requested to get out of my seat and come back to the flight attendants if I wanted water. 3 hour flight, some bumps, but seat belt sign off for about half the flight.

Both fights were delayed. Food could be better comparing to other international flights

Flight took off little late and landed back at YVR after an hour without informing a reason to the passengers. Also, second time also got late but an hour to take off. Therefore, I had to change my plans during due to delay in landing to SFO roughly about 6 to 7 hours.

Great crew and the plane was very nice! The problem was that we didn’t have WiFi on both of my flights. I found that to be very disappointing today when all the other airlines always have WiFi so I could work or watch a movie.

Even after booking in advance and getting to airport early, multiple delays and gate changes as well as forceful check in of bags even though it is within size and weight limits.

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

29/11Fri
directAir Canada
3h 54mORD-YYC
6/12Fri
directAir Canada
3h 28mYYC-ORD
C$ 274
29/11Fri
directAir Canada
3h 54mORD-YYC
6/12Fri
directAir Canada
3h 28mYYC-ORD
C$ 278
17/10Thu
1 stop
9h 28mORD-YYC
22/10Tue
1 stop
7h 38mYYC-ORD
C$ 300
19/10Sat
1 stop
7h 23mORD-YVR
25/10Fri
1 stop
17h 47mYVR-ORD
C$ 302
9/11Sat
1 stopPorter Airlines
4h 20mMDW-YUL
11/11Mon
1 stopPorter Airlines
6h 55mYUL-MDW
C$ 327
5/11Tue
1 stopUnited Airlines
8h 06mORD-YYC
19/11Tue
1 stopUnited Airlines
12h 41mYYC-ORD
C$ 328
29/11Fri
directUnited Airlines
3h 54mORD-YYC
6/12Fri
directUnited Airlines
3h 28mYYC-ORD
C$ 330
3/11Sun
directPorter Airlines
1h 42mMDW-YTZ
25/11Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 331
12/11Tue
1 stopAlaska Airlines
28h 43mORD-YYC
15/11Fri
1 stopAlaska Airlines
9h 02mYYC-ORD
C$ 334
12/11Tue
1 stopAlaska Airlines
28h 43mORD-YYC
15/11Fri
2 stopsAlaska Airlines
9h 30mYYC-ORD
C$ 347

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Recent one-way flight deals

31/10Thu
2 stops
18h 29mMDW-YVR
C$ 92
24/10Thu
1 stop
12h 40mORD-YYZ
C$ 107
6/12Fri
directAir Canada
3h 54mORD-YYC
C$ 115
12/11Tue
1 stopAir Canada
8h 13mORD-YYC
C$ 123
9/11Sat
1 stopUnited Airlines
6h 36mORD-YYC
C$ 129
9/12Mon
1 stopAlaska Airlines
16h 26mORD-YYC
C$ 131
31/10Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 145
2/11Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 146
6/11Wed
directUnited Airlines
1h 39mORD-YYZ
C$ 167
18/11Mon
1 stopAlaska Airlines
17h 49mORD-YYC
C$ 167

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Last minute flights from Chicago to Canada

Last minute flight, train and bus deals

13/10Sun
multi-stopDelta
11h 33mORD-YYC
19/10Sat
multi-stopDelta
9h 42mYYC-ORD
C$ 409
13/10Sun
multi-stopDelta
8h 35mORD-YYC
19/10Sat
multi-stopDelta
9h 42mYYC-ORD
C$ 453
15/10Tue
directUnited Airlines
4h 37mORD-YVR
19/10Sat
multi-stopUnited Airlines
12h 35mYVR-ORD
C$ 462
15/10Tue
multi-stopAir Canada
9h 38mORD-YVR
19/10Sat
multi-stopAir Canada
8h 55mYVR-ORD
C$ 464
15/10Tue
multi-stopAmerican Airlines
16h 03mORD-YVR
29/10Tue
multi-stopAmerican Airlines
14h 31mYVR-ORD
C$ 475
14/10Mon
multi-stopUnited Airlines
6h 36mORD-YVR
12/11Tue
multi-stopUnited Airlines
12h 21mYVR-ORD
C$ 476
12/10Sat
directAir Canada
4h 37mORD-YVR
14/10Mon
directAir Canada
4h 09mYVR-ORD
C$ 494
15/10Tue
directPorter Airlines
1h 39mMDW-YTZ
16/10Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 557
12/10Sat
directPorter Airlines
1h 39mMDW-YTZ
15/10Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 616
13/10Sun
directAmerican Airlines
3h 56mORD-YYC
19/10Sat
multi-stopAmerican Airlines
7h 01mYYC-ORD
C$ 631

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Everything you need to know for your flight from Chicago to Canada

Cabin class types available on flights to Canada
Cabin classes available on flights to Canada. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.