$59 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 9/22. 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.
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1 adult, Economy

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Best Canada Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
Toronto1 stop$154
Calgary
Calgarynonstop$157
Halifax
Halifax1 stop$383
Ottawa
Ottawa1 stop$257
Québec City
Québec City1 stop$372
Winnipeg
Winnipeg2 stops$258
St. John's
St. John's1 stop$448
Saskatoon
Saskatoon1 stop$250
Moncton
Moncton2 stops$488
Thunder Bay
Thunder Bay1 stop$375
Toronto
Toronto1 stop$154
Calgary
Calgarynonstop$157
Halifax
Halifax1 stop$383
Ottawa
Ottawa1 stop$257
Québec City
Québec City1 stop$372
Winnipeg
Winnipeg2 stops$258
St. John's
St. John's1 stop$448
Saskatoon
Saskatoon1 stop$250
Moncton
Moncton2 stops$488
Thunder Bay
Thunder Bay1 stop$375

Cheap Flights from Chicago to Canada

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Canada that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Canada

Thu, Sep 4 - Mon, Sep 15
Air Canada Logo
10:40 am - 1:54 pmORD-YUL
2h 14mnonstop
Air Canada Logo
8:20 am - 9:51 amYUL-ORD
2h 31mnonstop
$150Air Canada
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Tue, Sep 9 - Wed, Sep 10
United Airlines Logo
9:31 pm - 10:04 amORD-YYZ
11h 33m1 stop
United Airlines Logo
1:00 pm - 2:01 pmYYZ-ORD
2h 01mnonstop
$154United Airlines
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Thu, Jul 17 - Tue, Jul 22
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$157WestJet
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Tue, Jul 15 - Tue, Jul 22
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$158WestJet
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Tue, Oct 7 - Thu, Oct 9
Air Canada Logo
6:20 pm - 9:02 pmORD-YYZ
1h 42mnonstop
Air Canada Logo
1:00 pm - 2:01 pmYYZ-ORD
2h 01mnonstop
$164Air Canada
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Thu, Sep 18 - Wed, Sep 24
Porter Airlines Logo
9:15 am - 11:57 amMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$170Porter Airlines
Find Deal
Wed, Jun 25 - Wed, Jul 2
Porter Airlines Logo
5:50 pm - 8:32 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$171Porter Airlines
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Thu, Sep 18 - Wed, Sep 24
United Airlines Logo
9:31 pm - 10:04 amORD-YYZ
11h 33m1 stop
United Airlines Logo
5:15 pm - 6:12 pmYYZ-ORD
1h 57mnonstop
$177United Airlines
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Sun, Sep 7 - Thu, Sep 11
American Airlines Logo
8:25 am - 11:46 amORD-YUL
2h 21mnonstop
American Airlines Logo
5:15 pm - 6:50 pmYUL-ORD
2h 35mnonstop
$188American Airlines
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Sun, Sep 7 - Thu, Sep 11
American Airlines Logo
7:00 am - 10:57 pmORD-YUL
14h 57m1 stop
American Airlines Logo
5:15 pm - 6:50 pmYUL-ORD
2h 35mnonstop
$198American Airlines
Find Deal
Useful Info

KAYAK's insights & trends for Chicago to Canada flights

Get data-powered insights and trends into flights from Chicago to Canada to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Canada flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Canada.

The cheapest ticket to Canada from Chicago found in the last 72 hours was to Edmonton, at $122 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Toronto Pearson Intl Airport (YYZ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $136.

Can I save money by flying with a layover from Chicago to Canada?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $581 on average.

What is the cheapest month to fly from Chicago to Canada?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Canada, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Canada is July, when tickets cost $268 (return) on average. On the other hand, the most expensive months are November and January, when the average cost of round-trip tickets is $342 and $326 respectively.

What’s the cheapest day of the week to fly from Chicago to Canada?

The average price of all round-trip flights from Chicago to Canada clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Canada, look for departures on Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Canada, Friday is the cheapest day to fly and Monday is the most expensive.

How far in advance should I book a flight from Chicago to Canada?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Canada, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Canada, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$59
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Chicago O'Hare Airport to Montreal

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

Insights shared by verified travelers who flew the route from Chicago to Canada 
valerieFlew with Air CanadaORD-YULJan 2025
“Meal” usually means more than a light snack. I thought what they served was an appetizer not the total meal. So I’d eat before or bring food.
Verified travelerFlew with Air CanadaORD-YOWNov 2024
Ottawa, as a small airport is easiest to navigate! Overhead baggage compartments seem to be smaller, and on every flight they seem to need travellers to volunteer to put carryons in checked luggage instead.
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.
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.

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 from Chicago to Canada 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 from Chicago to Canada with an airline and back 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 from Chicago to Canada up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Canada?

    The cheapest time of day to fly to Canada is generally in the morning, when round-trip flights cost $568 on average. Morning departures are around 26% cheaper than evening flights, on average. The most expensive time of day to fly to Canada is generally in the evening, which is peak travel time and where the average cost of a ticket is $764.

Top tips for finding cheap flights to Canada

  • 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.

Top 5 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.
8.0
Porter AirlinesOverall score based on 288 reviews
8.7Crew
7.6Food
8.1Comfort
7.0Entertainment
8.2Boarding
Airline reviews

I love the 2 seats per row. More room. The crew were excellent.

10.0 ExcellentAnonymous, Apr 2025YHZ - YOW
Read more Porter Airlines reviews

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

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

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

We didn’t make the flight due to Delta’s check in line moving too slow.

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic! No entertainment possibilities. Not even a plug-in for phone or IPad if you wanted to watch a downloaded movie. Back to flying Air Canada!

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic!

The staff were the friendliest I have encountered in years. Absolutely great!

Plane changed to one with no entertainment system or ability to serve hot meals

Flight was delayed 3 times. Then cancelled due to pilot being timed out. They refused hotel vouchers. Gate attendants were very rude and could not help you at all.

Good. Would be better if the carry on baggage was free.

Horrible. I checked out myself that it seems that I can have a free carry-on. But they ask me to pay $75 when we are nearly boarding. It was tricky during check out that make you mistake that you can have a carry-on beside your personal item. Also they ask $75 in the airport instead of $35 during checkout. So the whole process is designed to make you this mistake

Westjet is one of the worst airlines in the world. 100% guaranteed to have flight delays and flight cancellations. Will never book again with Westjet.

Plane should have entertainment, instead of people paying to use wifi

Flight was delayed but the real issue is how long we sat after boarding. Space very limited for an overnight flight and seatbacks didn’t recline so it was almost impossible to sleep.

The staff made sure I was comfortable, moved me to a better seat with more leg room

Easy boarding and comfortable seating were plusses. Enjoyed the experience and good service from the captain and crew. Many thanks...!

Somehow, my booking was under my preferred name instead of my legal name so they almost didn’t let me board the plane at LAX. This problem should have been notified to me when I was still in Toronto.

Great overall. Quick boarding, attentive staff - great experience in premium class.

When arriving over 2 hours early to check k in at Charlotte airport I was told I would have to check my carry on ? Apparently the flight was full and may not be room. I was not given a choice and the agent was quite unpleasant about it. I am a senior amd was not comfortable me having to worry about my bag being lost vut it didn’t seem to bother him. There were lots and lots of people of all ages in line when we boarded with carryons and most larger than mine .the rest of my journey was pleasant vut this was totally unacceptable.

The layover was 6 PLUS hours and we were only given a $15.00 voucher. We missed our first activity in Quebec due to the delay.

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

It was a short flight, and no entertainment. That was not a problem for us, but there is no option for "not applicable". There was a bit of turbulence, so there was no food service.

the fact air Canada changed my flight from 850 PM to 815 AM with zero regard to the plans i made that last day, the cost i lost out on as things were non refundable amd shortening my first vacation in 7 years sickened me. when we purchase a service thats whats we expect. when we want to change the service we have to pay for that option but you do whatever you want . i called accessibility dept as i have a cpap and an implanted loop recorder first person said no problem just let security know you cant go thru scanners. then i got an email saying i had to fill out a fit to fly form . which again there was NO need to have that none. But that cost me money and time to have a doctor fill it out. then when i went to check in online i was declined i had to see a person at the airport instead. i couldnt get my boarding pass like everyone elseso here I was contacting air canada so I would have a easy travel experience and it ended up being a nightmare with more work for me, more cost and time. the flight itself was great the nightmare around it i will never subject myself to again. i tried to stick with supporting Canada but Air Canada was not worth supporting. very disappointed especially with a dept that is supposed to help disabled people not make an already challenging event not worth going thru at all.

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.

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