C$ 75 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 8/7. 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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Best Canada Flight Deals from Chicago

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

Ottawa
Ottawa1 stopC$ 295
Kelowna
Kelowna1 stopC$ 258
Québec City
Québec City1 stopC$ 575
Thunder Bay
Thunder Bay1 stopC$ 382

Cheap Flight Deals from Chicago to Canada (CHI-CA0)

 
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.

Recent round-trip flight deals from Chicago to Canada

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Canada.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Porter Airlines Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
4:05 p.m. - 4:54 p.m.YTZ-MDW
1h 49mdirect
C$ 195Porter Airlines
Find Deal
Sun, 8 Jun - Sun, 15 Jun
Porter Airlines Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
C$ 204Porter Airlines
Find Deal
Sat, 7 Jun - Sat, 14 Jun
 Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
 Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
C$ 222
Find Deal
Wed, 4 Jun - Wed, 11 Jun
Air Canada Logo
8:25 p.m. - 11:10 p.m.ORD-YYZ
1h 45mdirect
Air Canada Logo
8:15 a.m. - 9:09 a.m.YYZ-ORD
1h 54mdirect
C$ 223Air Canada
Find Deal
Thu, 19 Jun - Thu, 26 Jun
WestJet Logo
5:30 p.m. - 12:10 a.m.ORD-YVR
8h 40m1 stop
WestJet Logo
7:00 a.m. - 4:44 p.m.YVR-ORD
7h 44m1 stop
C$ 223WestJet
Find Deal
Fri, 9 May - Tue, 13 May
 Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
 Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
C$ 224
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Air Canada Logo
10:40 a.m. - 4:54 p.m.ORD-YYZ
5h 14m1 stop
Air Canada Logo
6:15 a.m. - 9:52 a.m.YYZ-ORD
4h 37m1 stop
C$ 226Air Canada
Find Deal
Sat, 7 Jun - Sat, 14 Jun
WestJet Logo
5:30 p.m. - 12:10 a.m.ORD-YVR
8h 40m1 stop
WestJet Logo
7:00 a.m. - 4:44 p.m.YVR-ORD
7h 44m1 stop
C$ 230WestJet
Find Deal
Thu, 29 May - Sat, 31 May
United Airlines Logo
7:10 a.m. - 9:58 a.m.ORD-YYZ
1h 48mdirect
United Airlines Logo
12:45 p.m. - 4:44 p.m.YYZ-ORD
4h 59m1 stop
C$ 233United Airlines
Find Deal
Sat, 17 May - Sat, 17 May
United Airlines Logo
7:40 p.m. - 8:32 a.m.ORD-YYZ
11h 52m1 stop
United Airlines Logo
11:00 a.m. - 12:03 p.m.YYZ-ORD
2h 03mdirect
C$ 242United Airlines
Find Deal
Sat, 17 May - Sun, 18 May

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 Calgary, at C$ 104 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 C$ 142.

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

The average price for all round-trip flights from Chicago to Canada depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Canada is generally in the evening, when round-trip flights cost C$ 339 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Canada is generally in the morning, which is peak travel time and where the average cost of a ticket is C$ 358.

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 1 stop layover the cheapest option at C$ 429 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 C$ 389 (return) on average. On the other hand, the most expensive months are November and April, when the average cost of round-trip tickets is C$ 478 and C$ 464 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 your flying dates are flexible, you should consider flying to Canada on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to Canada. For your return ticket, we recommend flying on a Friday and avoiding Tuesdays for the best deals.

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 23 weeks before departure.

Good to know

Low season

January

High season

July

Cheapest flight

C$ 75
Best time to beat the crowds (14% less expensive on average)
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Airport to Toronto Pearson Airport

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

Insights shared by verified travellers 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 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 Air CanadaORD-YULOct 2024
Ask questions to assure clarity. Don't assume you are receiving all of the information that you need.
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.
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.

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 travellers 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.

See more FAQs

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.
See more tips

Top 4 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 285 reviews
8.2Boarding
8.8Crew
7.6Food
8.1Comfort
7.0Entertainment
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.

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

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

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

Westjet has been absolutely terrible! Flights continually cancelled. Took 4 days to get home. Would have been 5, but we booked last flight with another airline after our Westjet flight was cancelled. Even pilot on original flight looked frustrated! Funny how they say cancelation is weather related, but they still have more than 1 other flight leaving to same destination on same day, but of course those are all full. This happened more than once on this trip. Two weather related cancelations and 1 mechanical. Not sure if the last flight even went ahead. Felt so sorry for families with kids and babies, and the older travellers. Felt like we lived out of suitcases and airports for days - SO RIDICULOUS! Next to no help from Westjet staff at airports, but it appears there is nothing they can help you with. Westjet has made it that they are unreachable when you need them! People were getting extremely frustrated, and rightfully so. Additional costs to us really added up, but Westjet literally DOESN'T CARE! Final straw was when we had to pay $1280 on a different airline (economy) trying to get home after another cancelled flight. Westjet will be refunding us a whole $140! Can't believe how this airline operates. We will never, ever use them again!

The only thing I didn’t like was how far away the gate was. I would have requested a wheelchair had I known.

no staff available to help, no systems available to coordinate

Flight was delayed. Arrived in Vancouver at 3 am. Not a great experience.

I hope these comments will find their way to AC customer experience team. Me and my spouse 50 years of aged coming back from 7 days perfect vacation... While boarding in FLL flight AC1621, one of the boarding agents (tall aged african american) man literelly yeld at my wife during the picture talking process. MAM ! STEP !! BACK !!! We are not illegal immegrants beying deported, nor are we in the millitary. We are customers returning home. This was unacceptable. While boarding in YYZ flight AC1154, one of the boarding agents (tall aged caucasian) man criticied with several complesant remarks my passport condition saying that I could not travel intl with it due to stain, decoloration, and BLOOD. My passport does not have blood on it! Yes it might be in less than perfect condition, but their are ways to talk to customer that does not imply not allow a boarding agent to be angry fathery like, or a custom agent looking at a suspicious individual. Both experience were less than acceptable for might I remind you a paying CUSTOMER returning home.

This flight didn't happen for me because of overbooking.

Poor air traffic controller staffing led to a 50%reduction on flights so we got to wait 4 hrs for our flight! Very disorganized at the gate Poor communication with customers

It was delayed by almost 90 minutes and that messed up our plans but it was beyond UA’s control that is what we heard

Terrible experience, flight was delayed both ways. Limited compensation for the 5+ hour delay. Will not be flying Air Canada Rouge, and don’t recommend you do either.

The boarding was relatively quick, the crew welcoming and flight uneventful. The omission of meals on all airlines is unacceptable especially when the flight is during a mealtime such as this one, (lunchtime), is unacceptable.

Everything was simple and easy. The lady at the gate was super friendly, I wish I had her name to share. She's a little older, dark-haired. You can tell she likes her job and would be a great influence on any young people training with her.

No Charging ports for personal electronics, which were required to use wifi entertainment.

Crammed in like cattle waited 30 mins for late connecting flight (flight didn’t wait for me for me when I missed my connection at 2 different airports on outward journey)

Rushed, the boarding was a great deal like a Chinese fire drill.

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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