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Find cheap flights from Chicago to Canada from $61

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 5/16. 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
0 bags
Sat 5/25
Sat 6/1

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Best Canada Flight Deals

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

Toronto
Toronto1 stop$220
Calgary
Calgarynonstop$204
Halifax
Halifax1 stop$333
Ottawa
Ottawa1 stop$376
Québec City
Québec City1 stop$412
Winnipeg
Winnipeg1 stop$330
St. John's
St. John's1 stop$547
Saskatoon
Saskatoon1 stop$310
Moncton
Moncton2 stops$511
Thunder Bay
Thunder Bay1 stop$578

Good to know

Low season

January

High season

July

Cheapest flight

$61
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago O'Hare Airport to Toronto Pearson Airport

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 to Canada from Chicago 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 to Canada with an airline and back to Chicago 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 to Canada from Chicago 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

  • Morning departure is around 18% more expensive than an evening flight, on average*.
  • 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
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
7.5
WestJetOverall score based on 2985 reviews
8.2crew
7.3comfort
6.5entertainment
7.7boarding
6.5food
Airline reviews

food worker strike caused lack of service. I know, not your fault but a bit of a inconvenience.

8.0 ExcellentMark, Apr 2024BNA - YYZ
Read more about WestJet reviews

food worker strike caused lack of service. I know, not your fault but a bit of a inconvenience.

The staff on the WestJet flight were friendly and helpful. The flight was smooth and we arrived 30 minutes ahead of time.

The on time performance and the ease of boarding are great. The crew were cordial. During landing the pilot made a hard landing with some swerve that was a bit rough but other than that everything else is as smooth as it can be.

Horrible, flight on the way to Vegas was delayed significantly and then on my way back my second flight was cancelled

If they have a tv for movie or map during 5h flight could be better and the food can purchase on flight are ok with that.

We requested 2 wheel chairs upon arrival. On board an attendant told us to remain in our seats until everyone was off the plane. we were in row 11 and thought we would be off early. After all were off, a different attendant said we should leave, and that the chairs were gone. One was available for my friend who had just spent 9 days in hospital but I had to walk quite some distance. Eventually a cart arrived to take us the rest of the way. This was over an hour after our arrival. The staff at the terminal did their best to help us but if we had been allowed off with the other passengers, our ride home would have been an hour earlier.

Our flight experience was great! Flight staff was funny and offered great service. Made record flying time coming home from Vegas after having to wait for planes on the tarmac because of high winds

Seats can use more cushioning, it felt very hard. The snack option could be better

Over all good. I had some issues with trying to buy my seat. The Westjet system kept trying to charge my credit card, without getting the seat. In the end after 5 times being charged, I got my seat.

I did not have a meal or entertainment, but flight was comfortable, beverage service was quick, crew was very helpful and pleasant. And a very smooth flight overall.

Wish we had music during take off and landing like the last flight

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

my seat got changed twice after checking on then boarding it had been given to a family so by the time they found a seat for me no overhead storage left. i ended up losing my Sony Headphones case because i could even access underthe seat in front of my when deplaning.

All good, useful to have the united app from check in to boarding

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

The flight was very uncomfortable and there was no snacks served for the 13 hours international flight. In addition, the flight was delayed 3 hours

Due to a strike taking place with the airline, it negatively impacted my flight in multiple ways. My flight was delayed over 2 hours and the food served was mediocre at best.

Cabin crew were great. Seats are criminal for tall people

Flight was delayed 1.5 hrs due to problem with a previous flight to mine; I was informed appropriately via Text & Email, however, website did not keep up with messages sent by nearly an hour. When checking-in warm & friendly reception at check-in desk until female Air Canada Rep noticed my flight number and instantly pivoted to a condescending & sarcastic comments about getting my bag checked in since I’m running so late; then tone instantly changed again few minutes later when she muttered, “Oh, they’ve delayed it” another sign systems & worse front line staff, not fully informed or simply not reading their flight status updates. Flight crew were very friendly & did a great job trying to make up lost time due to the delay.

It was great, love the experience and will definitely recommend 👌. Communication was great

My flight was great! Gate attendants and crew were great… pleasant and in good spirits. Flight delayed several hours and we were well informed of the status while on plane. Thank you!

The fact that I got to Toronto alive and well and safe is a huge plus. I thank the captain and crew for a safe flight The comfort of the aircraft leaves much to be desired. Human beings should not have to be that cramped and squashed on a flight that we pay a lot for and even have to pay for lousy food choices The cabin crew were pleasant and helpful Kudos to them as the flight was packed to capacity and there was a lot of work for them in a short space of time All in all a good experience, but too cramped

It was great to check carryon luggage at no charge when there was no room for ours. A hidden benefit of having low-tier tickets. Also great to stay off plane as long as possible. Airline gave us seats we wanted on this last leg, again at no charge.

The late departure Of two hours waitresses, immature, and gossiping

We had a good flight, service was good and lots of leg room. Service was good and the staff were friendly.

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

5/17Fri
nonstopWestJet
3h 27mORD-YYC
5/23Thu
nonstopWestJet
3h 35mYYC-ORD
$204
6/5Wed
1 stop
18h 20mORD-YYZ
6/12Wed
1 stop
17h 23mYYZ-ORD
$220
5/23Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
5/30Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
$252
5/23Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
5/30Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
$255
5/7Tue
nonstopUnited Airlines
3h 46mORD-YYC
5/15Wed
nonstopUnited Airlines
3h 30mYYC-ORD
$255
10/9Wed
nonstopAir Canada
3h 51mORD-YYC
10/13Sun
1 stopAir Canada
7h 53mYYC-ORD
$289
10/1Tue
1 stopAir Canada
8h 37mORD-YYC
10/5Sat
1 stopAir Canada
8h 43mYYC-ORD
$294
6/14Fri
nonstopUnited Airlines
1h 43mORD-YYZ
6/16Sun
nonstopUnited Airlines
1h 54mYYZ-ORD
$311
5/31Fri
1 stopAmerican Airlines
6h 00mORD-YYZ
6/2Sun
nonstopAmerican Airlines
1h 55mYYZ-ORD
$319
5/22Wed
1 stopAmerican Airlines
5h 04mORD-YYZ
5/28Tue
nonstopAmerican Airlines
1h 55mYYZ-ORD
$320

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Recent one-way flight deals

5/16Thu
1 stop
6h 47mORD-YYZ
$61
5/16Thu
1 stop
6h 47mORD-YYZ
$64
5/15Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$114
5/15Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$116
9/10Tue
1 stopUnited Airlines
9h 33mORD-YYC
$127
5/15Wed
nonstopAmerican Airlines
1h 35mORD-YYZ
$127
8/6Tue
nonstopAir Canada
1h 48mORD-YYZ
$129
5/15Wed
1 stopAir Canada
5h 46mORD-YTZ
$132
5/29Wed
nonstopUnited Airlines
1h 48mORD-YYZ
$133
6/23Sun
1 stopAmerican Airlines
16h 14mORD-YUL
$144

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Last minute flights from Chicago to Canada

Last minute flight, train and bus deals

4/30Tue
multi-stop
21h 38mORD-YVR
5/7Tue
multi-stop
13h 30mYVR-ORD
$299
4/30Tue
multi-stop
27h 36mORD-YVR
5/7Tue
multi-stop
11h 00mYVR-ORD
$309
4/28Sun
nonstopUnited Airlines
3h 46mORD-YYC
5/4Sat
nonstopUnited Airlines
3h 30mYYC-ORD
$401
4/30Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
5/1Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$411
4/28Sun
multi-stopUnited Airlines
15h 33mORD-YYC
5/4Sat
nonstopUnited Airlines
3h 30mYYC-ORD
$411
4/29Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
5/4Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$444
4/30Tue
nonstopAir Canada
4h 38mORD-YVR
5/2Thu
nonstopAir Canada
4h 13mYVR-ORD
$490
4/30Tue
nonstopAir Canada
4h 38mORD-YVR
5/2Thu
multi-stopAir Canada
7h 00mYVR-ORD
$495
4/28Sun
nonstopAmerican Airlines
1h 40mORD-YYZ
5/5Sun
nonstopAmerican Airlines
1h 55mYYZ-ORD
$528
4/30Tue
multi-stopAmerican Airlines
8h 04mORD-YUL
5/28Tue
multi-stopAmerican Airlines
10h 57mYUL-ORD
$534

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