C$ 76 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 30/9. 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
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
Ottawa
Ottawa1 stopC$ 440
Kelowna
Kelowna1 stopC$ 371
Québec City
Québec City1 stopC$ 486
Thunder Bay
Thunder Bay1 stopC$ 566
Ottawa
Ottawa1 stopC$ 440
Kelowna
Kelowna1 stopC$ 371
Québec City
Québec City1 stopC$ 486
Thunder Bay
Thunder Bay1 stopC$ 566

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

Sat, 11 Oct - Fri, 17 Oct
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
C$ 196WestJet
Find Deal
Tue, 9 Sep - Tue, 16 Sep
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
C$ 199WestJet
Find Deal
Sat, 13 Sep - Fri, 19 Sep
Air Canada Logo
3:35 p.m. - 11:16 p.m.ORD-YYC
8h 41m1 stop
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
C$ 212Air Canada
Find Deal
Mon, 15 Sep - Tue, 23 Sep
Air Canada Logo
6:20 p.m. - 1:12 a.m.ORD-YYC
7h 52m1 stop
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
C$ 217Air Canada
Find Deal
Mon, 15 Sep - Wed, 24 Sep
 Logo
3:50 p.m. - 11:22 p.m.ORD-YYC
8h 32m1 stop
 Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
C$ 218
Find Deal
Sat, 13 Sep - Fri, 19 Sep
 Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
 Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
C$ 225
Find Deal
Thu, 11 Sep - Mon, 15 Sep
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
C$ 226Porter Airlines
Find Deal
Thu, 4 Sep - Sun, 7 Sep
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
C$ 228Porter Airlines
Find Deal
Sat, 22 Nov - Sat, 29 Nov
United Airlines Logo
6:28 p.m. - 9:21 p.m.ORD-YYZ
1h 53mdirect
United Airlines Logo
5:30 p.m. - 6:39 p.m.YYZ-ORD
2h 09mdirect
C$ 232United Airlines
Find Deal
Wed, 3 Sep - Wed, 3 Sep
United Airlines Logo
8:50 a.m. - 2:19 p.m.ORD-YYZ
4h 29m1 stop
United Airlines Logo
5:15 p.m. - 6:12 p.m.YYZ-ORD
1h 57mdirect
C$ 239United Airlines
Find Deal
Booking Insights

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 Toronto, at C$ 92 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$ 92.

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 C$ 464 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 August, when tickets cost C$ 357 (return) on average. On the other hand, the most expensive months are November and January, when the average cost of round-trip tickets is C$ 469 and C$ 447 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 Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday 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 a flight from Chicago to Canada, you should book around 4 weeks before departure, which saves you about 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flightC$ 76
Best time to beat the crowds (14% less expensive on average)
Most popular time to fly (1% more expensive on average)
Flight from Chicago to Calgary

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

Insights shared by verified travellers who flew the route from Chicago to Canada 
NikhilFlew with Air CanadaORD-YYZJul 2025
small flight, not much storage space as per the passengers. Try to get a booking which is Group 1 or 2 latest.
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 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.

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

    The cheapest time of day to fly to Canada is generally at night, when round-trip flights cost C$ 249 on average. Morning departures are around 21% 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$ 337.

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.

Reviews of the top 4 airlines flying 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 318 reviews
7.6Food
8.7Crew
8.0Comfort
7.0Entertainment
8.2Boarding
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

Great! Personable crew. I love that they pour complimentary beer and wine.

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. :)

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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.

They cancelled and moved my flight with no email or text or any other notice. I discovered this only when I attempted to check in for my flight. Actual flying experience was above average.

They were on time and everything went as expected. The only thing that could be better was they didn't wait for us to get through customs to pick up our luggage off the carousel. An employee picked it up and was shoving it together with others onto a cart. Later we found one of our luggage was slightly bent.

Delayed boarding. Delayed taking off. Delayed landing. Missed our connecting flight. Our seats on this plane were not assigned until last minute, splitting up our family with kids. I sat in the last row next to the bathroom with so many people rubbing up against me to get to the bathroom the entire flight.

Another delayed flight. Then got bumped to a later connecting flight, over two hours later! Plane was hot and uncomfortable.

Asked to cancel flight 6 days in advance of flight back to St. Louis, MO. Would not allow. No credit either.

Crew was nice especially by North American standards. Bad good. No entertainment screens. Terrible WiFi

Not only was the flight delayed more than 3 hours but also there was no internet or movies on the flight. It was Flair/Spirit quality of experience at Westjet prices

West Jet flight was cancelled and I was not notified. I found out when I tried to check in on-line. Spent 4 hours on the phone with West Jet and Just Fly trying to figure what happened.

Only issue was checking in took over an hour and was very stressful. It all worked out, but we weren't sure for a while.

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

Both flights are delayed so I rate the whole experience as mediocre.

I booked my flight months ago, and checked-in online about 12 hours before the flight. I received an email confirmation of check-in. I had no subsequent communication from Air Canada after my original booking. After arriving at the airport three hours before the flight, as instructed, I waited 90 minutes for an agent to appear to check my bag. I was informed that my flight had been canceled many weeks before, and that flight was no longer being run!! I showed a copy of my check-in confirmation, but no explanation could be found. I was placed on standby for the next flight and the connection. Luckily, those flights were not full and I arrived at my destination. I double checked my email, but I received no update about the flight from Air Canada until the day of the flight.

I had a good experience. I liked being informed about the status of my luggage

I was forcefully re-routed to another destination and was delayed a total of 8hours. I have still not received my bags, no one is taking responsibility. The agents at the airport lied to me that I will get to my destination same time as my previous flight where I was forcefully re-routed from.

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Our flight was canceled at the last minute. Someone on the flight said the exact same thing happened to her the day before. I will say they helped us book a flight on another airline so that we could still make our vacation with little delay.

We had a very long delay. First the inbound flight took a while, then maintenance, they “fixed it” to then do boarding and leave the gate, and waste a lot of time to have to go back to the gate and eventually deplane. Had to wait for a new aircraft, wait for a gate, and do the whole thing again. Instead of leaving at 9:50am we left until past 1. I could’ve not woken up at 5am, or spend some more time with my family if they gave more grace period of time between flights to give some time in case of any issues. But they have to make all and every dollar possible

Aircraft had technical issues. After 3 hours of trying to resolve, flight was cancelled. Was booked on a flight leaving 12 hours after intended departure. Now on 4 flights instead of 2 and a day late to my destination.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

I am very tall. All airline seats are a bit uncomfortable.

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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