
Cheap Flights from Chicago to Canada
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook Cheap Chicago to Canada Plane Tickets
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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 ticket to Canada from Chicago found in the last 5 days was to Toronto, at $146 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 5 days was $211.
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 $419 on average. Morning departures are around 46% 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 $794.
Can I save money by flying with a layover from Chicago to Canada?
No, with an average price for the route of $580, prices are generally cheapest when you fly direct.
What is the cheapest month to fly from Chicago to Canada?
The cheapest month for flights from Chicago to Canada is February, when tickets cost $336 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $443 and $428 respectively.
What’s the cheapest day of the week to fly from Chicago to Canada?
If you are looking for a flight deal from Chicago to Canada, look for departures on Thursdays 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 get a below average price on the flight from Chicago to Canada, you should book around 3 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.
Which airlines fly non-stop between Chicago and Canada?
There are 8 airlines that fly nonstop from Chicago to Canada. They are: American Airlines, Qatar Airways, Air Canada, Porter Airlines, Qantas Airways, Delta, WestJet and United Airlines. The cheapest price of all airlines flying this route was found with Air Canada at $128 for a round-trip flight to Calgary (YYC). On average, Delta offers the best prices for nonstop flights between Chicago and Canada.
Which airlines fly most frequently between Chicago and Canada?
Chicago and Canada are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (239 flights per week), Air Canada (231 flights per week), and Air New Zealand (109 flights per week).
How long does a flight from Chicago to Canada take?
The duration of a flight to Canada depends on your arrival airport. The shortest routes to Canada from Chicago are to Toronto, which takes 1h 59m, Montreal, which takes 2h 56m, and Winnipeg, which takes 3h 33m.
Which cabin class options are there for flights between Chicago and Canada?
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
What’s the earliest departure time from Chicago to Canada?
The earliest flight from Chicago to Canada departs at 7:03 am, landing in Toronto at 9:47 am.
What’s the latest departure time from Chicago to Canada?
If you prefer to fly at night, the latest flight from Chicago to Canada jets off at 9:21 pm and lands in Toronto at 11:59 pm.
Good to know
Low season | February |
|---|---|
High season | July |
Cheapest flight | $109 |
Flights from Chicago to Canada: the best tips from KAYAK users
FAQs - booking Canada flights
Top tips for finding cheap flights to Canada
Reviews of the top 5 airlines serving from Chicago to Canada
A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..
A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..
The flight booking code given by Kayak was not the correct one used by the airline. I had to call to get the correct one. It was never sent to me. Totally unacceptable!
Much roomer than air Canada! Great flight for the price. No complaints
As a first time flyer with Porter I was happy with the service and comfort of the airline.
Other than wifi no on board entertainment. Will use them again, roomier seats than other airlines and snacks and beverages, better than average
I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc
The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.
There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!
Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.
Flight was delayed over 2 hours, then landed at a different airport!
On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.
The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive
Not United Airlines' fault. It's ORL airport's fault.
Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.
Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.
Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.
We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.
Delay and keep changing gates. I have to run around from B to C then to E.
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.
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
Our flight was delayed 3x and we were unaware until 15min of arriving at the airport so had we been made aware sooner we could have enjoyed possibly another 4hrs poolside. Very frustrating. Made the next day going back to work extremely tough too.
It was ok. Jet was ok but it lacked many convinces we have experienced on other airlines such as in seat entertainment. Space seamed more compact than other airlines. They did not provide the gate to gate assistance we arranged for for our mom who needed a wheel chair.
Due to delays at SFO, my WestJet light missed its connecting WestJet flight. If they had held the plane in Calgary for 15 minutes, 2 families with children would not have been stranded in Calgary for more than 24 hours. I understand the need to be on-time, but when it is the same company, you would think they could make a phone call. Or maybe they could go to a higher altitude to make up for lost time? Instead of attempting to put us on another flight, they rescheduled us for the same connecting flight 24 hours later. We then had to scramble to find a hotel, which they state that they were not responsible for since the delay was not their fault and therefore became an additional out of pocket expense for us. The customer service is severely lacking here at this company. They also mentioned that if we purchased our tickets through a 3rd party site (Kayak) versus WestJet directly, that they couldn't help us. Seriously?? Additionally, we lost 2 days of travel and missed out on tours and taxis that were pre-booked. I will not be using WestJet again,
This airline would not refund my money and I had a physician note that I could not fly. They are crooks
Westjet was late and we missed our connecting flight with Cathay. Had to wait 8 hours. Westjet only allows 1 checked in baggage for international flights- it’s always been 2. Canada allows only 1 sandwhich bag size full off small liquids. Everything else will be tossed. Awful trip. Will never fly west jet or go to Toronto to connect flights!
No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,
Flight was good, crew was excellent. No complaints at all
Delayed 3 times in a row for 4 hours total. Incrementally pushing back the flight claiming gate delays but they eventually changed the actual plane, due to technical issues. This strategy to avoid compensation to passengers is unprofessional.
Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable
Everything was good except for flight delay, but it was because of the snow storm in the arrival airport.
Boarding was delayed 50 minutes. The flight going to Chicago was canceled, causing lots of problems and causing me to rebook and miss an event. I was traveling with a colleague, and he was unable to get on the same flight after 40 minutes on the phone, which meant I had to wait for him after my arrival. My flight down was delayed an hour before take off, had to sit on the plane, then 30 minutes after landing to get to a gate. No real food, only juice/ water offered for the 3.5 hours on the plane. Not a good experience.
The code sharing reservation with United was messed up requiring extra trip to airport to fix. Air Canada customer service 2.5 hours on hold and resolved nothing.
I'm 6'8" (2.03m) so more legroom would alwqys be appreciated, especially on long international flights. The food choices were underwhelming.
Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight
the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)
Short flight. Everything was fine except the flight was delayed twice for a total of an hour.
There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.
Very bad, flight was cancelled due to strike and staff was unable to rebook us
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.
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.
First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.
My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.
The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.
After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.
DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.
AA was fine....the overall experience was subpar, but not due to the airline due to broader issues
No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.
Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.
The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.
Flight was delayed and so much of inconvenience related to the gate change.