$54 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 10/31. 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
Toronto
Torontononstop$146
Calgary
Calgarynonstop$185
Halifax
Halifax1 stop$389
Ottawa
Ottawa1 stop$340
Québec City
Québec City1 stop$378
Winnipeg
Winnipeg1 stop$279
St. John's
St. John's2 stops$477
Saskatoon
Saskatoon1 stop$327
Moncton
Moncton2 stops$503
Thunder Bay
Thunder Bay1 stop$413
Toronto
Torontononstop$146
Calgary
Calgarynonstop$185
Halifax
Halifax1 stop$389
Ottawa
Ottawa1 stop$340
Québec City
Québec City1 stop$378
Winnipeg
Winnipeg1 stop$279
St. John's
St. John's2 stops$477
Saskatoon
Saskatoon1 stop$327
Moncton
Moncton2 stops$503
Thunder Bay
Thunder Bay1 stop$413

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, Nov 6 - Tue, Nov 11
United Airlines Logo
4:50 pm - 7:45 pmORD-YYZ
1h 55mnonstop
United Airlines Logo
9:00 pm - 9:59 pmYYZ-ORD
1h 59mnonstop
$146United Airlines
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Thu, Aug 14 - Thu, Aug 21
Air Canada Logo
3:35 pm - 6:50 pmORD-YUL
2h 15mnonstop
Air Canada Logo
6:40 pm - 8:16 pmYUL-ORD
2h 36mnonstop
$156Air Canada
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Thu, Nov 6 - Tue, Nov 11
United Airlines Logo
6:02 am - 1:43 pmORD-YYZ
6h 41m1 stop
United Airlines Logo
8:55 am - 10:00 amYYZ-ORD
2h 05mnonstop
$156United Airlines
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Thu, Aug 14 - Thu, Aug 21
Air Canada Logo
10:40 am - 4:55 pmORD-YYZ
5h 15m1 stop
Air Canada Logo
2:10 pm - 3:04 pmYYZ-ORD
1h 54mnonstop
$158Air Canada
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Mon, Sep 22 - Fri, Sep 26
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
$185WestJet
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Mon, Sep 8 - Mon, Sep 15
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
$186WestJet
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Thu, Aug 14 - Thu, Aug 21
Porter Airlines Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$191Porter Airlines
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Mon, Aug 18 - Sun, Aug 24
Porter Airlines Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$193Porter Airlines
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Mon, Sep 1 - Wed, Sep 10
American Airlines Logo
8:10 am - 11:36 amORD-YUL
2h 26mnonstop
American Airlines Logo
5:15 pm - 6:50 pmYUL-ORD
2h 35mnonstop
$203American Airlines
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Mon, Sep 1 - Fri, Sep 5
American Airlines Logo
8:10 am - 11:36 amORD-YUL
2h 26mnonstop
American Airlines Logo
2:31 pm - 8:27 pmYUL-ORD
6h 56m1 stop
$219American 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 $124 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 $167.

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 $587 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 $266 (return) on average. On the other hand, the most expensive months are November and January, when the average cost of round-trip tickets is $341 and $324 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 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 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$54
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 3% 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 $560 on average. Morning departures are around 27% 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 $766.

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 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 296 reviews
7.6Food
8.1Comfort
7.0Entertainment
8.7Crew
8.2Boarding
Airline reviews

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

10.0 ExcellentSteve, Jun 2025LAS - YOW
Read more Porter Airlines reviews

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. :)

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.

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.

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

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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

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.

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.

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.

Bad experience boarding and flight got delayed didn’t make it to my next flight

The food on the trip Toronto to Athens could be better: the chicken didn’t taste good.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

The plane is too cramped! Zero leg room and when the person in front of me put their seat back they were basically laying in my lap.

Before final boarding, my husband and I — both seniors — were told that we could not bring our carry-on bags with us due to being in Zone 6. The staff took our bags with little explanation, stating it was policy. While we understand boarding procedures may vary by zone, the way we were spoken to was unnecessarily rude and dismissive. We felt disrespected and singled out, and the interaction left us deeply uncomfortable. As seniors, we expect to be treated with courtesy and dignity, especially during travel when accommodations and communication matter most. We hope you will look into this matter and ensure better training for staff in handling such situations with more empathy and professionalism.

They canceled my flight and then refused to reschedule me on another flight. I had to take a train. No compensation. I won't use Air Canada again.

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.

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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