Find cheap flights from Chicago Midway Airport to Canada
Good to know
|January||Best time to beat the crowds with an average 3% drop in price.|
|July||Most popular time to fly with an average 19% increase in price.|
Average price round-trip
|$305||(avg. price over the last 2 weeks)|
Good deal round-trip
Good deal one-way
Top tips for finding cheap flights to Canada
- Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to Canada for the following prices or less: to Toronto $88 one-way - $199 round-trip
- Book at least 3 weeks before departure in order to get a below-average price.
- High season is considered to be November and December. The cheapest month to fly to Canada is August.
- Morning departure is around 127% more expensive than an evening flight, on average*.
FAQs - booking Canada flights
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Top 3 airlines serving Chicago Midway to Canada
Scores according to KAYAK customer reviews
Pros: "All of it"
Cons: "Nothing Best flight"
Pros: "The flight landed early. Check-in staff were great."
Cons: "Boarding was a debacle. Flight was oversold. Passenger had trouble boarding when their group was called."
Pros: "There was an available seat next to me"
Cons: "I had to walk from one end of Minneapolis airport to the other end all within 35 mins to catch a connecting flight, tram was not in service. Not fun!!!"
Pros: "The crew was amazing. Kat and the other stewards were very friendly."
Cons: "Maybe the option for free upgrade to first class if flight is not full??"
Cons: "Delays were unfortunate, but the gate area at LaGuardia was way too crammed, hardly any seats, and poorly organized"
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Cons: "Passengers should have the option to ask for additional snacks."
Pros: "top notch KLM are the best"
Pros: "Crew was amazing."
Pros: "Good snacks"
Cons: "At least one hour late"
Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."
Pros: "Extra leg room was great"
Cons: "Entertainment system was flickering"
Pros: "Enjoyed the ease of check in the spacious gate and the cleanliness of the planes cabin"
Cons: "No complaints"
Pros: "Crew were helpful and pleasant"
Cons: "Seating was uncomfortable, cabin was cold and no blankets available, food was just ok, plane had lots of empty seats yet everyone was squeezed into 3 in a row making it uncomfortable, no updates from captain or crew as to where we were in the flight....."
Pros: "Entertainment available"
Cons: "All good"
Cons: "The baggage drop attendant was very unhelpful when I asked if she could help me sort out an issue (when I checked in online for the second leg of my trip, i paid for my bag then but they wanted me to pay again for my first flight) and just dismissed me and said she couldn't help, making me pay again for my bag. First time I've ever had an unpleasant experience with Delta."
Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."
Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"
Pros: "On time, great service, a lot of legroom."
Cons: "Flight delayed, nearly missed connecting flight"
Pros: "Everything went smoothly. The staff were friendly, the flight fast and calm."
Cons: "Nothing that can be done, just tough being 6'5" in a connection plane."
Pros: "Left on time all went well in Atlanta"
Cons: "Impossible to figure out what to do in Toronto at Canadian Customs. You move from secure to unsecure then back to secure. It’s a mess and nobody tells you what to do or where to go. Picture process took 4 times. Nobody tells you that you have to transfer your own bags from Delta to West Jet. I even asked in a Toronto and they said no and nobody in Atlanta told me to collect my bags. So bags never made it until the next AM. The West Jet rep was very good and located the bags and they were delivered as promised. You should provide 3 page detailed instructions on how to handle Toronto. I am a seasoned traveler by the way. I’ve never seen anything worse. I could go on and on."
Cons: "was a difficult transition from delta to west jet in Toronto and we almost missed the flight"
Cons: "Could not get the boarding pass to print at the self serve kiosk. Had to wait in line for assistance."
Pros: "Delta and Westjet staff are of great help to me."
Cons: "Not applicable"
Pros: "The staff is very friendly. Most pleasant airline I've flown with."
Pros: "On time as scheduled."
Pros: "Left early and arrived early."
Cons: "Smallest bathroom on a plane I've ever seen. Could barely sit down without my knees banging into door or wall."
Pros: "The flight attendant named Steven went so far beyond the call. He was attentive, he fixed our video system when no one else could and when he learned we were celebrating an anniversary he brought us a present. He was awesome!"
Pros: "Refurbished plane. Lighting was good"
Cons: "No TV screen"
Pros: "Overall the actual flight was good..landing was kind of hard but I'm alive so not stressing that"
Cons: "..but the multiple delays are ridiculous, I would not fly Delta if I had a feasible choice."
Cons: "No space in the seats"
Pros: "Boarding was smooth. Gate rep helped us kindly and then the flight attendant was very friendly."
Cons: "3 hours there before the departure."
Cons: "Why can't all the Delta gates be near each other. My connecting flight was very far."
Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."
Cons: "They were rude and notnhelpful lost my luggage"
Cons: "Not a fan of having "final boarding call" announced to run to the gate, only to sit on the plane at the gate for 30 min because of a scheduled delay at my destination. I know the flight wasn't very full, but that cost me an opportunity to eat dinner. I had to cancel a fast food order because I thought I'd miss my flight!"
Cons: "Snacks if possible"
Pros: "That a delta plane actually had seat back video screens- First delta flight ever that I've been on that did. But every ones screen froze up just over an hour into the flight."
Cons: "Even though the Atlanta to Toronto arrived 'early' I had barely 20 minutes to get to the other plane- I would not have made it with out the amazing staff of weather and the Toronto airport. I use a wheelchair and even zipping through as fast as I could I was 15 minutes late arriving at the gate. I booked this flight thinking I had at least and hour and a bit between flights. Thankfully others on my flight were also late so the Ottawa bound plane did not leave on time"
Pros: "When you are delayed, there is not much to commend."
Cons: "Delayed. That pretty well says it all."
Pros: "The crew was good and the flight was smooth."
Cons: "Somehow we were double booked and double billed. We got to the airport 3 hours early and checked our bags. All 3 were lost and searched. Everything was put back precariously and there was shampoo and lotion everywhere."
Pros: "i love the view from the window seats and that I was able to relax and the snacks."
Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."
Pros: "Plane was comfortable"
Cons: "In order to leave airport on time (plane came in late) they claimed overhead space was full and that remainder boarding passengers had to check their bags. (Bags to be picked up in baggage claim) When walked into plane saw plenty of overhead space for carryons!"
Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."
Pros: "Free wine and beer service"
Cons: "Gate agents, re-booking"
Pros: "On time; easy boarding check-in"
Cons: "It would be such a nice touch if you could set up coffee and breakfast snack in the terminal waiting area."
Cons: "Flight delayed but good"
Cons: "Honestly, even if the aircraft was delayed, there is nothing one can do and just be patient. Lunch and dinner vouchers were issued, that was well appreciated!"
Cons: "Leaving on time!"
Cons: "Time to de-board took some time"
Cons: "Nothing really. Maybe new planes ?"
Pros: "The crew is really good. Super nice and attentive."
Cons: "Honestly, while the flight delay was a hassle. Probably nothing because flight delays happen. My bag was placed on the next flight. But your crew’s attitude made it all better."
Cons: "Nothing really"
Pros: "Thank you for using glasses and not plastic!!!!!!"
Cons: "Wish I could fly them all the time. Really a great experience."
Pros: "Flight was late but importamt is, it was safe take off and landing. Very nice service, good welcome staff and there was free snaks and drinks. Wonderfull overall"
Cons: "May be proper update online or more announcements. But because of weather it is understable."
Pros: "Great crew"
Cons: "Nothing was bad"
Pros: "Good timing. No delays"
Cons: "Couldn't figure out my frequent flier number and the call-in centre wanted me to wait for some crazy amount of time to figure it out. Kind of insulting."
Cons: "Noisy aircrafts"
Pros: "The attitude of crew was good and comfortable seats and good service we shoul have plug to charge devices"
Pros: "Crew were very professionally and very attentive to my needs as a mom traveling with an infant."
Pros: "It was quick and easy to board the plane with no dlays"
Cons: "A little bumpy"
Pros: "Snacks and pleasant mannerism of the stewardess"
Pros: "I had an excellent flight back home. We left about 15 late but the pilot made up the time so arrival in TO was on time"
Cons: "Pd392 seat I sat in was a bit uncomfortable it appears to be sinking in the center unlike the plane plane i took from TO to Chicago"
Pros: "Service of crew and snacks"
Cons: "Flight was delayed."
Cons: "To avoid additional headache when passengers are boarding the plane, I would recommend boarding the “first class” first then start with the back seats then make your way to the front seats. It will be a much smoother process when getting everyone onto the plan."
Pros: "The earlier flight departure times are really good, the traffic is not jammed yet on the 401 and GEW. Custom waiting times are basically non existing in comparison to Pearson. Planes are relatively on time (only flew 4 times with Porte), staff is friendly. The turboprop planes have more legroom than most others. I do like them, and do recommend Porter."
Pros: "it was such a smooth flight"
Cons: "all good"
Pros: "Comfy large seats. Great service"
Cons: "Little slow to leave"
Pros: "Nice flight"
Cons: "Highly recommend it"
Pros: "Staff was nice everywhere during this trip."
Cons: "I was charged $40 for my bag at O'hare because my booking to Montreal was done as two separate tickets (as the staff explained)....?!?! Kayak how do you do this and not tell your customer? $40 dollars is not a lot but I definitely feel cheated!"
Pros: "Nice crew, snacks and drinks, good price, calm experience."
Cons: "All flights delayed by 1 hour. Maybe equipment logistics could be better."
Pros: "Literally nothing. Even the free beer and wine didn't make up for this company!!"
Cons: "Our flight to Chicago was cancelled, we didn't get so much as an email letting us know (checked the flight status at 1am for a 8am flight and it said on time) we found out at the porter counter at the airport that or flight was cancelled and we were delayed until the next day!!! Next day we realize they didn't schedule us on the first OR second flight of the day but the third so we were delayed by 36 hours instead of 24!!!! The planes are tiny, very old, quite dirty. The staff seem totally non chalant about all these cancelled flights and allllll of the delays and repeatedly say that the airline is understaffed... hello i don't care why my vacation was cut short by 36 hours and i got stuck paying 200$ for a hotel room tat i didn't get to stay in!!! Get your act together Porter!!!!"
Pros: "Everything else... the whole Porter Experience brought me back to what air travel used to be like... I will fly Porter again. Even a long weather delay was more tolerable because the waiting area was more like a Flight Club experience."
Cons: "Baggage rules seemed to be enforced arbitrarily... gate Checking was routine... but I was forced to pay to check a bag."
Pros: "The flight attendants were very nice. Timely boarding."
Cons: "Very small plane with only one bathroom."
Cons: "They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service."
Pros: "Snacks and the complimentary wines"
Cons: "Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines."
Pros: "My trip going to Toronto has been canceled on friday and moved for the following day, I had to by another flight going to toronto so i don't miss the commitement i had this is not acceptable they should have offered me to place my flight for another time"
Pros: "Free wine & beer! :)"
Pros: "All the complimentary food and drinks, really nice staff and comfy and elegant seatings."
Cons: "There needs to be better coordination, or perhaps the actual truth, regarding making connections when first flight is delayed. Also, correct info regarding the location of facilities when one has to pick up bags after immigration and drop them off before security for second flight. I have traveled to Canada many times before and Porters personnel were among the least helpful I have ever encountered in over 30 years of regularly coming North."
Pros: "The flight was on time and overall it's a smooth travel experience. Definitely recommend to friends n family."
Pros: "I liked nothing!"
Cons: "Re: my flight to Toronto where I met someone who spoke Spanish. I started a nice conversation with her and in the back I understood a couple of Americans using racist terms directed towards us. No one on the flight staff stepped in to interject or intervene. Maybe they did not hear the comments but it was difficult not to. I believe they avoided the issue and I was left feeling uncomfortable and discriminated against in a seat I paid $400+ for. I should not have to feel that way when paying so much for a service and I will not be recommending Porter to anyone or using your airline again without a proper response from Porter."
Pros: "The service and the crew,."
Cons: "The connecting flight was delayed by 1h30 ."
Cons: "Flights were delayed both directions"
Pros: "On time Bags received promptly"
Cons: "Baggage I checked in one bag only I did it online and was charged 31dollars US why? I live, in hk and was in Canada for flight and flight check in. Why not charged me the promised 25 dollars why us and why so high. My way to Quebec was 25 dollars Canadian ?"
Cons: "비행기 지연, 4시간 30분 기다림. 예정 도착시간보다 5시간 늦게 도착"
Pros: "Fast boarding"
Cons: "The landing was a bit rough"
Pros: "Everything was good."
Cons: "We had to pay for a different flight, unless we waited until the next day. Which was impossible for us. So that sucked."
Pros: "Entertainment n/a hence the one star. My flight was surprisingly affordable and I felt like I was being treated well because porter serves their cold beverages in these mini glasses made of glass (not plastic cups) with 'porter' written on them. I also got a complimentary snack on this 1.5h flight vs my parents who took a different 5h flight with AC and they got no complimentary snacks. It's the little things that make a difference these days. I also loved the Billy Bishop airport. We landed around sunset so the view of the skyline was beautiful and we were right at the water."
Pros: "Staff were very friendly and efficient, no issues with boarding or in flight."
Cons: "Flight was delayed but we were notified ahead of time so wasn't a problem."
Pros: "very nice."
Pros: "I’m very good"
Cons: "There was not enough room for my carryon for some reason and so I had to sit with my knees up and feet on my bag. Not the worst but there should be enough carry on space for everyone."
Pros: "The staff were nice enough on the plane"
Cons: "They said we were pre boarding so we went and stood in line with our 2 year old. Finally after 15 minutes they actually started letting the line through when they could have just waited 15 minutes to even announce the pre-boarding line. Then we boarded the plane and it was late and another 30 minutes waiting to fly. There was no TVs.. and whatever, we brought our iPad We got to Edmonton and our car seat was quite damaged. West jet couldn’t give us anywhere near the car seat we have and not one that fits in my car."
Pros: "It was overall ok , but over all disappointing that west jest became such a budget airline."
Cons: "I’m disappointed that west jet became such a budget airline, it used to be my favourite. Now there’s no monitors, you got to use up your own power from devices. I prefer to save my battery when travelling."
Pros: "Everyone was kind and helpful. Keep up the good work."
Cons: "Trip was too short."
Pros: "I had a 5 month old baby and the crew was super smiley and friendly. Also, the flight wasn't full so there was plenty of room. I really enjoyed my experience. Thank you Westjet!"
Pros: "This was my first time flying Plus and I don't think I can ever go back. Worth every penny."
Pros: "Most things"
Pros: "The staff was nice, they were very professional, efficient, and friendly, The seats were comfortable the plane was clean."
Cons: "Some of the announcements were a bit fuzzy."
Pros: "Friendly staff"
Cons: "All flights boarded late, they ran out of food for purchase on long flights and the seats are uncomfortable."
Cons: "How there was no boarding call and we missed our flight."
Pros: "Airport Terminal waiting area was nice."
Cons: "Changed planes, changed seats after paying for advanced booking. Service was poor, cabin was hot."
Cons: "Seat space was too tight"
Cons: "Good Choice of movies to watch on my tablet, but sound was really bad, worse than when i play my music from my tablet on the same earphones"
Pros: "The snacks were good"
Cons: "They lost my checked sleeping bag which forced me to buy another one before my backpacking trip. They refused to refund me for it costing me an extra few hundred dollars to replace it. To include I paid an extra eighty dollars for my trip because apparently I requested window seats which I wasn't provided for my return flight home! Be prepared to lose your luggage and don't expect a refund!"
Pros: "The courtesy of the flight crew, and above all, the smooth flight conducted by the Captain.T"
Cons: "There were no specific "hiccups" or negativity pertaining to the flight."
Cons: "The long delay, 2 kids crying continuous, no place to smoke, no one explained to me that I had to pick up my luggage in Toronto! So now my suitcase is delayed! I was told that it would go straight through to destination. I will never use Delta again! And I will not fly through Detroit or Toronto again!!!"
Pros: "Really great attendants. Friendly and humorous."
Cons: "They took the tablets pretty early it felt. 45 minutes before we landed. But other than that, great experience!"
Pros: "Flights were on time"
Cons: "Bad landings"
Pros: "Cabin crew was excellent, very professional, friendly, and helpful. The flight itself was smooth, and on time."
Cons: "Lack of access to entertainment without having our own personal device to view and having to download an app to be able to view entertainment"
Cons: "My flight was not actually booked going to Edmonton and I had to rebook it at the airport to go home. Coming back to Fort McMurray my flight was also cancelled without telling me and I had to buy another ticket."
Cons: "Great flight"
Pros: "Pleasant crew. Flight left & arrived on time."
Pros: "Food, attendants, comfort, entertainment"
Cons: "Manual boarding and missing one of my luggage"
Cons: "Flight delayed, crew didn't remove garbage before landing."
Pros: "Regular seating on this West Jet flight was great, very comfortable with ample room."
Pros: "Constant thanks from crew for the passenger patience with delays due to flight crew, and then weather delays - 2 hrs total Liked the captain came out to speak, clearly I might add, to explain the weather delays and provide updates..."
Cons: "Can't complain about what was beyond my control, but flight crew needing to come from another flight and then the other side of the airport to set up, resulting in hour delay - seems like alternative should have been available or system needs a process review to improve efficiency"
Pros: "We were delayed while in the plane. The steward decided to give drinks and snacks on the house which in the end lightened the atmosphere. It did make it late for the Oilers play-off game which was likely very important to many of the business men on the flight."
Cons: "Could not figure out how to get their entertainment app to work."
Cons: "cabin was too hot"
Cons: "Delayed 8 hours."
Pros: "We were given seats in the Plus section on the short leg to Calgary."
Cons: "The plane was about 1.5 hours late arriving. A person was sick or drunk and had to deplane. It took over an hour to find his luggage and reload all the luggage. We missed our connecting flight to Calgary as a result and had to stay overnight in a hotel in Edmonton."
Pros: "Friendly staff at check-in and on flight. It had arrived early and so we were boarded early and left."
Cons: "Our flight heading to PSP was a different story. We were 2 1/2 hours late getting away, including the necessary deicing."
Pros: "Boarding was very smooth,the crew was excellent, and a very smooth flight."
Cons: "we sat in row 17 which was the last row to be served refreshments, when they finally got to us there were no sandwiches left and very little else to purchase."
Cons: "Seats are tooo small. Plane too warm and air nozzle pressure too weak. Shape of window made seat even more narrow. Wow!"
Pros: "It's a short flight. Crew was good."
Pros: "Liked the price and small airport in Abbotsford. No complaints."
Pros: "The staff and the friendly service."
Cons: "It would be better to know beforehand what kind of entertainment we can expect, whether it is by WestJet app, or small TV screen. That way you can plan ahead what you need on the plane."
Pros: "I like direct flights. The foot room is quite adequate for normal sized people like ourselves. Staff were very friendly. Check in is fast through self serve when a person travels with carry-on luggage only."
Cons: "Our seat choices were extremely limited because we used self check-in and wanted adjacent seats. We were seated at the back of the plane for both flights even though the planes were only 65% or so full. Negotiating the aisles to the back of the plane is difficult for a 94 year old even if not handicapped or using ambulatory assistance. We only had carry-on luggage and did not wish to stand in line for a ticket agent. We felt slighted that young able-bodied single persons had closer seating. If we need to lie and say an elderly person is not ambulatory just to be given fair treatment, please indicate this in booking instructions."
Cons: "Reservation went smoothly as dealt directly with WestJet to book flight. Staff all very friendly and helpful. I do find the food is less than desirable for snacks. Could there not be some recycling on all the waste generated on a flight?"
Cons: "The lady, Serena, constantly pumped my shoulder which I recently had surgery on. Every time she walked by I would move over, squishing the person beside me, so she wouldn't hit me but yet she went out of her way to and even hit my chair several times. She was also extremely rude, I asked for water and she told me no she also wouldn't take my garbage when she had the garbage bag in her hand. I highly recommend not taking west jet."
Cons: "Delays and missed connections."
Pros: "Staff friendly, flight on time"
Cons: "in flight service consisted of crackers and water. No entertainment other than westjet magazine."
Pros: "To seats on the 767 are comfortable and more spacious than the 757."
Cons: "Flight was delayed due to mechanical issues. New plane was sorted, flight left 5 hours late."
Pros: "free wine row to myself"
Pros: "The speed"
Cons: "Small seats"
Pros: "Great customer service Good snacks Excellent flight - no turbulence"
Cons: "No WestJet Connect Seats were a little squished with no ability to lift the armrest"