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Find cheap flights from Chicago to Canada from $81

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 7/31. 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
0 bags
Sat 6/22
Sat 6/29

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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$215
Calgary
Calgarynonstop$203
Halifax
Halifax1 stop$298
Ottawa
Ottawa1 stop$328
Québec City
Québec City1 stop$369
Winnipeg
Winnipeg3 stops$326
St. John's
St. John's1 stop$490
Saskatoon
Saskatoon1 stop$274
Moncton
Moncton2 stops$456
Thunder Bay
Thunder Bay1 stop$578

Good to know

Low season

January

High season

July

Cheapest flight

$81
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago O'Hare Airport to Calgary

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 2% 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 2895 reviews
8.2Crew
6.5Entertainment
7.7Boarding
7.3Comfort
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.

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

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

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.

This was a red eye return, so I doubt there would be anyway to make it better. Other than adding beds.

Direct nonstop flight was great. Flight was delayed and the crew announced a 2h delay on the sound system. 30 min or so later I hear my name on the sound system for immediate board. Several other passangers were late too. Reason: The crew incorrectly announced a 2h delay when in reality they meant a new boarding time at 2pm.

Plenty of room in the exit row. Sat on the plane an hour before taking off.☹️ Landed late and had to wait for gate availability.

Flight was on time early arrival better entertainment good staff.everything was excellent

Delayed leaving. On arrival we were taken to the airstrip and had to get off onto an over crowed bus, not all that passengers fit. Drove around the airport for 20 + minutes. Taken off the bus told to go upstairs 3 flights then all the passengers had to walk a mile or more , those of us old there was no one to direct us to were to go. I asked several people with no answers. Once I got to baggage claim my bags were not on the right bag claim. Once again asked for help and finally someone found my bags on a different carasel. Very frustrating.

Excellent host on board. Not so friendly check-in staff. Older plane with no food or entertainment due to short flight. Friendly captain and crew.

I don’t think there was entertainment? No mention of it. It was a good flight. Only complaint was my seat cushion was not attached and kept slipping.

They canceled the flight on us very close to the flight date .

It took 66 hours to get from Seattle to Tel Aviv. As a minor, I was left for more than 12 hours in Toronto and Frankfurt without hotel and food vouchers. It took 5 layovers. It was insane and not okay

It was delayed but got us to YYZ. I had great copassengers.

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

8/16Fri
nonstopWestJet
3h 45mORD-YYC
8/21Wed
nonstopWestJet
3h 27mYYC-ORD
$203
7/29Mon
nonstopWestJet
3h 45mORD-YYC
7/31Wed
nonstopWestJet
3h 27mYYC-ORD
$209
6/7Fri
nonstopAir Canada
3h 46mORD-YYC
6/13Thu
nonstopAir Canada
3h 29mYYC-ORD
$224
6/7Fri
nonstopUnited Airlines
3h 46mORD-YYC
6/10Mon
1 stopUnited Airlines
16h 34mYYC-ORD
$239
8/3Sat
1 stopAir Canada
7h 50mORD-YYC
8/6Tue
1 stopAir Canada
7h 01mYYC-ORD
$241
6/13Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
6/17Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$248
6/17Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
6/24Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$249
6/11Tue
1 stopAmerican Airlines
15h 45mORD-YUL
6/12Wed
nonstopAmerican Airlines
2h 39mYUL-ORD
$271
6/11Tue
1 stopUnited Airlines
11h 19mORD-YYZ
6/12Wed
nonstopUnited Airlines
2h 02mYYZ-ORD
$279
6/8Sat
1 stopAmerican Airlines
9h 08mORD-YYZ
6/14Fri
nonstopAmerican Airlines
1h 55mYYZ-ORD
$322

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Recent one-way flight deals

7/31Wed
nonstopWestJet
3h 45mORD-YYC
$81
9/20Fri
nonstopWestJet
3h 50mORD-YYC
$82
6/15Sat
nonstopAir Canada
1h 45mORD-YYZ
$94
8/4Sun
1 stopAir Canada
8h 55mORD-YYC
$97
6/21Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$105
6/6Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$107
6/21Fri
nonstopUnited Airlines
1h 52mORD-YYZ
$122
8/12Mon
1 stopUnited Airlines
11h 36mORD-YYZ
$132
7/21Sun
nonstopAmerican Airlines
2h 30mORD-YUL
$151
8/8Thu
1 stopAmerican Airlines
15h 31mORD-YUL
$161

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Last minute flights from Chicago to Canada

Last minute flight, train and bus deals

5/27Mon
nonstopWestJet
3h 27mORD-YYC
5/31Fri
nonstopWestJet
3h 35mYYC-ORD
$234
5/28Tue
multi-stop
6h 47mORD-YYZ
6/1Sat
multi-stop
9h 43mYYZ-ORD
$287
5/27Mon
nonstopAir Canada
4h 20mORD-YVR
5/29Wed
nonstopAir Canada
4h 14mYVR-ORD
$339
5/27Mon
nonstopAir Canada
4h 20mORD-YVR
5/29Wed
multi-stopAir Canada
7h 41mYVR-ORD
$344
5/27Mon
multi-stopUnited Airlines
11h 05mORD-YVR
6/1Sat
nonstopUnited Airlines
4h 01mYVR-ORD
$348
5/26Sun
multi-stopUnited Airlines
11h 05mORD-YVR
5/28Tue
multi-stopUnited Airlines
8h 53mYVR-ORD
$353
5/28Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
6/5Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$404
5/25Sat
multi-stopAmerican Airlines
7h 45mORD-YVR
6/1Sat
multi-stopAmerican Airlines
7h 44mYVR-ORD
$417
5/28Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
6/1Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$433
5/28Tue
nonstopAmerican Airlines
1h 35mORD-YYZ
6/5Wed
nonstopAmerican Airlines
1h 55mYYZ-ORD
$460

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