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Find cheap flights from Chicago to Canada from C$ 100

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 5/6. 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 1/6
Sat 8/6

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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 stopC$ 261
Ottawa
Ottawa1 stopC$ 450
Kelowna
Kelowna1 stopC$ 562
Québec City
Québec City1 stopC$ 508
Thunder Bay
Thunder Bay1 stopC$ 775

Good to know

Low season

January

High season

July

Cheapest flight

C$ 100
Best time to beat the crowds (8% less expensive on average)
Most popular time to fly (3% more expensive on average)
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 12% 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 4 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 2970 reviews
7.3Comfort
6.5Entertainment
7.7Boarding
8.2Crew
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.

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

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.

Very good other than we have to wait for one crew and we’re delayed and the pilot and his co- pilot has to make a difference to be right on time arrival. Disappointed about no food service also.

I had written all my complaints on my trip from Grand Junction to Denver so I will repeat it here! I was absolutely appalled that I had to pay for a regular seat that I choose 24 hrs before boarding! Also I checked my large bag which I had to pay for as well, and by the time I boarded all the room in the bins were gone so also had to check that one. I noticed people pulling out oversized suitcases, bigger than the measurements stated for carry on, and also large pack packs stuffed full! So these people were taking up 2 or 3 spaces that the rest of us should have been able to use but couldn’t! NoTV on the flight! Thankfully I had downloaded the United Airlines app and was able to watch movies on my phone. Don’t remember the last time I flew in a plane with no movie screens!

Easy boarding, roomy seats, plenty of good food, very helpful snd friendly staff. Very smooth flight! Only thing that could have been better was to have cranberry juice. Women like this as it helps avoid UTI’s and not as sweet as other juices.

The crew was friendly, the seats are too small. Air travel is barely tolerable anymore.

Food was icecold or frozen including breakfast. Hopeless service. Rude crew.

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

Book cheap flights from Chicago to Canada

Recent round-trip flight deals

28/5Tue
1 stop
18h 20mORD-YYZ
5/6Wed
1 stop
12h 10mYYZ-ORD
C$ 261
14/5Tue
1 stop
18h 20mORD-YUL
26/5Sun
1 stop
9h 44mYUL-ORD
C$ 264
6/6Thu
directWestJet
3h 27mORD-YYC
9/6Sun
directWestJet
3h 35mYYC-ORD
C$ 307
6/6Thu
directWestJet
3h 27mORD-YYC
8/6Sat
directWestJet
3h 35mYYC-ORD
C$ 334
28/5Tue
directPorter Airlines
1h 42mMDW-YTZ
4/6Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 350
22/5Wed
directPorter Airlines
1h 42mMDW-YTZ
1/6Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 352
25/5Sat
1 stopUnited Airlines
15h 51mORD-YUL
26/5Sun
directUnited Airlines
2h 43mYUL-ORD
C$ 414
21/9Sat
1 stopAir Canada
8h 59mORD-YYC
28/9Sat
1 stopAir Canada
7h 16mYYC-ORD
C$ 418
14/6Fri
directUnited Airlines
1h 43mORD-YYZ
19/6Wed
directUnited Airlines
1h 57mYYZ-ORD
C$ 428
22/5Wed
directAir Canada
1h 45mORD-YYZ
7/7Sun
directAir Canada
1h 56mYYZ-ORD
C$ 432

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Recent one-way flight deals

5/6Wed
1 stop
18h 20mORD-YYZ
C$ 100
15/5Wed
1 stop
18h 20mORD-YUL
C$ 107
15/7Mon
directWestJet
3h 45mORD-YYC
C$ 154
18/6Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 161
6/6Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 162
15/7Mon
directWestJet
3h 45mORD-YYC
C$ 162
31/5Fri
directUnited Airlines
1h 48mORD-YYZ
C$ 183
29/5Wed
directAir Canada
2h 23mORD-YUL
C$ 187
4/7Thu
1 stopAir Canada
5h 57mORD-YYZ
C$ 190
17/6Mon
1 stopUnited Airlines
9h 13mORD-YYZ
C$ 194

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Last minute flights from Chicago to Canada

Last minute flight, train and bus deals

6/5Mon
multi-stopDelta
10h 30mORD-YYC
18/5Sat
multi-stopDelta
5h 47mYYC-ORD
C$ 414
6/5Mon
multi-stopDelta
10h 30mORD-YYC
10/5Fri
multi-stopDelta
5h 47mYYC-ORD
C$ 431
4/5Sat
directAir Canada
3h 44mORD-YYC
7/5Tue
directAir Canada
3h 30mYYC-ORD
C$ 506
4/5Sat
directAir Canada
3h 46mORD-YYC
6/5Mon
multi-stopAir Canada
7h 48mYYC-ORD
C$ 522
7/5Tue
directPorter Airlines
1h 42mMDW-YTZ
11/5Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 538
7/5Tue
directPorter Airlines
1h 42mMDW-YTZ
10/5Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 584
6/5Mon
directUnited Airlines
3h 44mORD-YYC
10/5Fri
directUnited Airlines
3h 30mYYC-ORD
C$ 724
6/5Mon
directUnited Airlines
3h 44mORD-YYC
18/5Sat
directUnited Airlines
3h 30mYYC-ORD
C$ 772
3/5Fri
multi-stopWestJet
5h 10mORD-YYZ
6/5Mon
multi-stopWestJet
26h 31mYYZ-ORD
C$ 784
6/5Mon
multi-stopWestJet
4h 42mORD-YUL
13/5Mon
multi-stopWestJet
4h 28mYUL-ORD
C$ 790

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Flights to Canada

Return flight deals:

Canada - Chicago

Cabin classes:

C$ 1,358
C$ 1,412
C$ 161