$104 Find Cheap Flights from Chicago to Canada - Compare and Save

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Cheap Flights from Chicago to Canada

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Toronto
Torontononstop$222
Calgary
Calgary1 stop$329
Halifax
Halifax1 stop$488
Ottawa
Ottawa1 stop$416
Winnipeg
Winnipeg1 stop$354
Québec City
Québec City1 stop$499
St. John's
St. John's2 stops$627
Saskatoon
Saskatoon1 stop$443
Moncton
Moncton1 stop$700
Thunder Bay
Thunder Bay1 stop$602
Toronto
Torontononstop$222
Calgary
Calgary1 stop$329
Halifax
Halifax1 stop$488
Ottawa
Ottawa1 stop$416
Winnipeg
Winnipeg1 stop$354
Québec City
Québec City1 stop$499
St. John's
St. John's2 stops$627
Saskatoon
Saskatoon1 stop$443
Moncton
Moncton1 stop$700
Thunder Bay
Thunder Bay1 stop$602
Booking Insights

Price, demand and travel trends for Chicago to Canada flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Chicago to Canada cheaper or more expensive than last year?

Fares from Chicago to Canada are running about 8% higher than they were around this time last year, averaging $408 round-trip.

What are the cheapest fares from Chicago to Canada right now?

Here are the cheapest round-trip fares from Chicago to Canada on KAYAK in the last week:

• Toronto Pearson Intl (YYZ) from $221
• Montreal Pierre Elliott Trudeau Intl (YUL) from $322
• Vancouver Intl (YVR) from $324
• Calgary (YYC) from $329
• Winnipeg (YWG) from $354

What’s the cheapest month to fly from Chicago to Canada?

May is the cheapest time of year to fly, with average fares of $359. Prices are highest in July, when average flight costs increase to around $476.

When is the best time to book flights from Chicago to Canada?

Book your flights 5 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 35% compared to booking last-minute (within 2 weeks of departure).

Which airport in Canada is the cheapest to fly to from Chicago?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Canada are:

• Toronto Island (YTZ) from $289
• Toronto Pearson Intl (YYZ) from $314
• Calgary (YYC) from $402

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

Friday tends to be the cheapest day to fly from Chicago to Canada, while Monday is the most expensive. Fares run about 12% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago to Canada?

Data from the past 12 months shows it's cheapest to fly to Canada during the night with average prices of $393. The morning is the most expensive time to fly, with average prices of $467.

Key details for Chicago to Canada flights

Low season

February

Cheapest flight

$104
Beat the crowds with an average 50% drop in travelers.
The most popular month to fly with an average 103% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Toronto Pearson Intl Airport

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

Insights shared by verified travelers who flew the route from Chicago to Canada 
MonyeeFlew with United Airlines-Sep 2026
Chicago is a large airport so it takes time to commute from one gate to another.
ScottFlew with Air Canada-Jun 2026
Make sure you have enough time between connecting flights so ½ of your baggage doesn't miss the flight and take another 24hrs to show up
NikhilFlew with Air Canada-Jul 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 Canada-Jan 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 Canada-Nov 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 Airlines-Sep 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
Verified travelerFlew with United Airlines-Jan 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.

Your Chicago to Canada flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago to Canada?

    Yes. Fares from Chicago to Canada are low right now. As a rule of thumb, a round-trip under $294 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Chicago to Canada?

    Over the past 12 months, round-trip fares from Chicago to Canada have ranged from $294 to $625.

  • What are the main airports serving Canada?

    Canada has 37 airports. The three busiest are Toronto Pearson Intl (YYZ) (24% of arrivals), Calgary (YYC) (19%) and Montreal Pierre Elliott Trudeau Intl (YUL) (17%).

  • What airlines fly nonstop from Chicago to Canada?

    Based on the flight schedule for the next 3 months, 5 airlines offer nonstop flights on this route:

    • United Airlines
    • Air Canada
    • American Airlines
    • Porter Airlines
    • WestJet

  • Where in Canada can I fly nonstop from Chicago?

    You can fly nonstop from Chicago to 8 destinations in Canada. Some of the most popular among KAYAK travelers include Toronto, Calgary, Montreal, Vancouver and Québec City.

  • Is it cheaper to fly with a layover from Chicago to Canada?

    Yes. Nonstop flights from Chicago to Canada average $394 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Washington, D.C. Dulles Intl (IAD) from $261
    • Salt Lake City (SLC) from $325
    • Edmonton (YEG) from $358

  • How long is a flight from Chicago to Canada?

    Nonstop flights take 2h 18m on average. The fastest scheduled flight takes 1h 37m, from Chicago O'Hare Intl (ORD) to Toronto Pearson Intl (YYZ).

  • How often are flights from Chicago to Canada delayed and what's the average delay?

    23% of flights on this route are delayed by at least 15 minutes. The average delay is 1h 58m.

  • Which cabin classes are available on flights from Chicago to Canada?

    On flights from Chicago to Canada you can book Economy Class, Premium Economy Class, Business Class or First Class.

  • What are some popular landmarks in Canada?

    KAYAK travelers' favorite landmarks in Canada include:

    • Rogers Centre
    • BC Place Vancouver
    • Union Station
    • Scotiabank Arena

  • What are the earliest and latest flights from Chicago to Canada?

    The earliest nonstop flight from Chicago to Canada departs at 6:54 am and the latest departs at 9:22 pm. Nonstop flights take about 2h 18m.

  • 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.

Your guide to booking Chicago to Canada flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 5 weeks before your trip. KAYAK data shows fares in this window are around 35% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for May when flights are typically cheapest and avoid July when prices are at their highest.
  • Flying on Friday is usually the cheapest. Flights on Monday cost about 12% more on average, so being flexible with your travel dates could help you save.
  • If arriving on time matters more than price, consider flying with one of the most punctual airlines on this route: American Airlines, United Airlines, Air Canada, WestJet and Delta.
  • If you're looking to save, Toronto Island (YTZ) is the cheapest airport to fly into from Chicago. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in Toronto, which is the most popular destination in Canada. From there, it's easy to continue on to other popular destinations such as Niagara Falls, Vancouver and Montreal.
  • If you want the shortest trip, choose the nonstop route from Chicago Midway Airport to Canada. If you'd rather save money, the route from Chicago Greater Rockford Airport via Washington, D.C. Dulles Intl (IAD) is usually the cheapest.
  • 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 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 468 reviews
7.6Food
7.0Entertainment
8.2Boarding
8.0Comfort
8.6Crew
Airline reviews

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..

6.0 GoodHarsh, Apr 2026
Read more Porter Airlines reviews

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.

I have posted the comments in the first flight leg.

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.

More options for your flight from Chicago to Canada

Complete your trip to Canada with a hotel stay or car rental