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$73 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 9/1. 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 8/24
Sat 8/31

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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$191
Calgary
Calgary1 stop$198
Halifax
Halifax1 stop$272
Ottawa
Ottawa1 stop$361
Québec City
Québec City1 stop$348
Winnipeg
Winnipeg1 stop$274
St. John's
St. John's2 stops$398
Saskatoon
Saskatoon2 stops$327
Moncton
Moncton2 stops$426
Thunder Bay
Thunder Bay1 stop$351

Good to know

Low season

January

High season

July

Cheapest flight

$73
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago Midway Airport to Vancouver

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 10% 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.
7.6
Porter AirlinesOverall score based on 344 reviews
6.8Entertainment
7.6Food
7.7Comfort
7.8Boarding
8.4Crew
Airline reviews

Chaotic boarding, but mostly my issues are with Toronto airport

6.0 GoodArti, Jul 2024YYZ - YUL
Read more about Porter Airlines reviews

Chaotic boarding, but mostly my issues are with Toronto airport

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Service was amazing, and the plane was comfortable even for this long haul. But they could have more movies selections. But they were still a lot to choose from.

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!

Horrible! I paid for a straight flight from Chicago to London. A week before trip it changed and now I had a connecting flight. Our flight was delayed an hour and a half because our flight crew was still flying in from CA. Forty passengers ran from one plane to the next. The next United Airlines flight was delayed two to three hours because of mechanical difficulties. They had to ready another plane which took time. I missed my scheduled excursion in London. 😢

My flight was delayed for a whole day, so I lost a day of my vacation.

United cancelled the flight after a 2 hour delay. The only choice was a 24 hour delay which was then 3 hours delayed.

flight delayed, was put on another flight after standby queue, luggage was misplaced and arrived to me 3 days later

The baggage handlers broke the handle on my bag that they put under the plane that I checked on the jetway. They traded it out for a less quality bag in Tulsa. But, they said they would try to fix it. Bologna! There was no fixing that bag handle. Someone didn’t care how they treated the bag.

Flighty delayed on boarding - then group 1 had to check their carry on bags but groups 3 and beyond could carry bags on - very inconvenient for weekend business trip with no checked baggage. Then delayed on the runway - before take off. No communication from pilot on why or how long. Wifi/Entertainment didn't work for 4+ flight. Upon arrival, attendants announced wrong carousel for baggage claim - everyone was waiting at the wrong place for their checked bags. This was a mess united!

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

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

Okay but not like typical first or business class. On domestic airlines

Hey it got me from A to B on time on a crazy day. No food is offered in board No entertainment options And worst of all, no communication regarding baggage claims in Atlanta!! Having precleared CBP in Canada and landing at a domestic gate I expected to pickup baggage at the domestic terminal. No indication in app of where to pick up bag. No text message from WestJet. So I went to domestic where my bag was NOT. Do you know what a pain it is to get from domestic terminal to international at ATL? 45 min ordeal. My bag was still on the carousel, along with many other WestJet bags from mine and other flights. I pity any arriving customer not familiar with ATL trying to find their bags in this circumstance. And then no way to catch Marta from international. This falls far below the standards expected of modern airlines.

The flight attendants were amazing. But we checked in online and just needed to check our bags. The line was so long that it took over an hour to do this. There was only one person checking people in.

I liked the kindness of the check in counter crew, the flexibility with changing seats and the comfort. Better free drink selection would have been good but it wasn't a long flight.

Did not realize this was a super budget airline - we even had to pay for a carry on!

I understand that delays may be inevitable; however, the airline did absolutely nothing to reassure us during our flight. There were no apologies for the delay and business resumed as usual. A little compassion should have been garnered for our almost 4 hpur delay.

20+imite delay on the plane with no air. Part of our group had no seats assigned and took a long time to get fixed. Again no wifi and snacks were sad

The first flight was cancelled so they automatically re-booked me to fly out *2 days* later. I had to call and spend over an hour on hold to get a new flight. Woke up the next morning to find out the new flight had been delayed enough that I wouldn't be able to make my connection so I called again, spent another hour+ on hold, and then got disconnected. Called again, another hour+ on hold to find out they couldn't find a replacement flight that would get me to my destination in time for my meetings so I had to cancel my trip. Note that the original flight cancellation and the delay of the 2nd flight were both due to "staffing issues".

We were informed of an impending mechanics and technologists strike between June 18-20 with the potential to delay or cancel flights. This put an enormous amount of stress on us as our flights from Phoenix-Calgary-Vancouver were a precedent to our cruise leaving Vancouver on June 21. The first leg of our flight had no WestJet Connect. Both planes were model 737-700 . There was no room under the seats for typical personal items as a plastic housing for flotation devices prevented stowage. Center seat had a large power supply (thinking USB retrofit) that consumed 1/3 of the area for your feet. No beverage service Calgary to Vancouver. Never flying WestJet ever again.

Flying is no fun anymore. Too little space. Too much carry on baggage slowing down everything.

Perfect flight. Efficient boarding, on time take off and early arrival. Generally smooth flight.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

BAD. As a family could not sit together. The gate agent told us there was only one seat in the middle left, when we got on the plane the situation was very different with whole rows of seats empty

Plane was delayed an hour causing me to miss my flight to London and now I am not arriving until Sunday instead of Friday. I am stranded at airport and they give me $12 of food vouchers. It's a joke and everyone I talked to was rude

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

When you pay for Premium Economy and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

The plane was freezing cold. Normally I’m fine on planes but I needed to toss a sweatshirt on this time.

I missed this flight due to delays on my previous flight.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

Hard to criticize after the Crowd Strike dilemma. However, when Air Canada says they were "not affected," I expect that is true. My flight delays caused me to miss transportation connections. I understand these things happen, but I don't have to "like it."

Flight was canceled 2 hours ahead. Just as I arrived at the airport

Great flight crew. Flight delayed but still made connection because I rushed through the terminal. If I’d waited for the requested wheelchair I never would have made the next flight. Also, there was no one readily available to ask for assistance, I had to search for assistance. The workers at customs seemed annoyed to help.

I paid for an exit row seat but it did not have a TV. Pretty bad for a 4 hour flight

It’s very good.. keep up the good job!!! Thank U.

Everything nice. Only nice staff and kind people. Thank you Air Canada. I will be back ❤️

They changed the seats that we paid for 3 times after we booked and paid for them causing me to have to call them. We had a connecting flight from my through Montreal and on to Calgary. It was raining in Montreal and they left our luggage outside in the rain. Water seeped into the luggage soaking our clothes. This was our first and last time traveling on air Canada. Use another reputable carrier, not them

Internet wouldn’t work even after I paid for the package. That was my only real complaint, otherwise excellent.

Great flight! Service, food and flight experience were top notch.

No ac last 1/2 hour of flight. Simply awful. I almost got sick

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

10/10Thu
1 stop
13h 04mMDW-YVR
10/15Tue
2 stops
11h 40mYVR-MDW
$183
9/4Wed
1 stop
18h 58mORD-YVR
9/9Mon
2 stops
20h 18mYVR-ORD
$184
8/23Fri
1 stopPorter Airlines
4h 43mMDW-YUL
8/25Sun
1 stopPorter Airlines
6h 37mYUL-MDW
$236
8/23Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
8/30Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$237
8/19Mon
1 stopAir Canada
10h 59mORD-YVR
8/28Wed
nonstopAir Canada
4h 05mYVR-ORD
$239
9/18Wed
nonstopAir Canada
3h 44mORD-YYC
9/26Thu
1 stopAir Canada
7h 01mYYC-ORD
$239
9/5Thu
1 stopAmerican Airlines
5h 15mORD-YYZ
9/8Sun
nonstopAmerican Airlines
1h 54mYYZ-ORD
$239
8/19Mon
1 stopUnited Airlines
8h 39mORD-YVR
8/28Wed
nonstopUnited Airlines
4h 05mYVR-ORD
$245
8/22Thu
nonstopUnited Airlines
1h 32mORD-YYZ
8/25Sun
nonstopUnited Airlines
1h 56mYYZ-ORD
$256
8/13Tue
nonstopAmerican Airlines
1h 50mORD-YYZ
8/13Tue
1 stopAmerican Airlines
9h 14mYYZ-ORD
$283

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Recent one-way flight deals

9/1Sun
2 stops
17h 19mMDW-YVR
$73
9/17Tue
1 stop
22h 04mMDW-YYC
$74
9/23Mon
nonstopAir Canada
3h 44mORD-YYC
$91
8/15Thu
1 stopPorter Airlines
4h 40mMDW-YUL
$97
8/24Sat
1 stopPorter Airlines
5h 33mMDW-YUL
$99
9/14Sat
nonstopAir Canada
2h 10mORD-YUL
$100
8/23Fri
1 stopUnited Airlines
11h 48mORD-YYC
$106
7/31Wed
1 stopUnited Airlines
13h 57mORD-YYC
$111
8/13Tue
nonstopAmerican Airlines
1h 50mORD-YYZ
$122
9/27Fri
nonstopAmerican Airlines
2h 10mORD-YUL
$141

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Last minute flights from Chicago to Canada

Last minute flight, train and bus deals

7/30Tue
multi-stopAir Canada
9h 14mORD-YYC
8/28Wed
nonstopAir Canada
3h 29mYYC-ORD
$244
7/30Tue
multi-stopAir Canada
9h 14mORD-YYC
8/27Tue
multi-stopAir Canada
7h 26mYYC-ORD
$254
7/29Mon
nonstopWestJet
3h 45mORD-YYC
8/5Mon
nonstopWestJet
3h 27mYYC-ORD
$341
7/29Mon
nonstopWestJet
3h 45mORD-YYC
8/1Thu
nonstopWestJet
3h 27mYYC-ORD
$346
7/30Tue
multi-stopUnited Airlines
8h 33mORD-YVR
8/7Wed
multi-stopUnited Airlines
11h 21mYVR-ORD
$374
7/30Tue
nonstopUnited Airlines
4h 38mORD-YVR
8/6Tue
multi-stopUnited Airlines
13h 24mYVR-ORD
$375
7/30Tue
nonstopAmerican Airlines
4h 45mORD-YVR
8/6Tue
multi-stopAmerican Airlines
13h 00mYVR-ORD
$402
7/27Sat
multi-stopAmerican Airlines
9h 45mORD-YVR
8/8Thu
multi-stopAmerican Airlines
7h 39mYVR-ORD
$420
7/27Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
7/31Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$488
7/30Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
8/7Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$508

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