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Find cheap flights from Toronto Island to Chicago

YTZ - CHI

Find cheap flights from Toronto Island to Chicago

Round-trip
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Toronto (YTZ)
Chicago All airports
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Good to know

Low season

November Best time to beat the crowds (29% less expensive on average)

High season

January Most popular time to fly (56% more expensive on average)

Average price round-trip

C$ 379 (avg. price over the last 2 weeks)

Good deal round-trip

C$ 200 or less

When to book flights from Toronto Island to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 255 or less round-trip.
  • The cheapest flight from Toronto Island to Chicago was found, on average, 36 days before departure.
  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be December, January and February. The cheapest month to fly is November.

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Top airlines flying Toronto Island to Chicago

Scores according to KAYAK customer reviews

7.7
Porter Airlines
Overall score based on 2,710 reviews
7.8
Boarding
7.8
Comfort
8.3
Crew
6.8
Entertainment
7.8
Food
Airline reviews

Pros: "Nothing"
Cons: "Porter declined re-booking the flight due to weather conditions and forced us to purchase new tickets. Reservations made through anything other than Porter are treated poorly, service can be declined due to overbooking."

Pros: "Efficient check in. Liked the shuttle bus service from subway to airport."
Cons: "As expected this is a commuter flight so very stripped down in terms of amenities. Tight plane seating and those overhead bins just barely accommodate the carry on."

Pros: "The crew was helpful and everything was on time."
Cons: "The ride was a bit rough at the end if the flight."

Pros: "The crew is lovely"
Cons: "Porters flights out of Toronto have been significantly delayed every time I’ve flown"

Cons: "Flight was delayed"

Pros: "All ok"
Cons: "Not a thing"

Pros: "Fast and convenient"

Pros: "First time in 10 flights in 3 months flying with Porter in time - what a miracle!"

Pros: "Free bar nuts while delayed 10 hours"
Cons: "Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be"

Pros: "Once we got on the flight it was fine."
Cons: "Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages."

Pros: "It was hassle free. Trace and arrival times were perfect. Thank you for caring."

Cons: "Got to Billy Bishop, only to find out flight is delayed 2 hours."

Pros: "Convenient, easy boarding, snacks and free wine on leg from toronto to chicago"

Cons: "Major delays that were poorly handled."

Cons: "Delay"

Pros: "Easy. Relaxed. Cheap. Great!"

Pros: "fast"
Cons: "no TSA precheck"

Pros: "Lounge Snacks"

Pros: "I liked the lounge"
Cons: "There were a lot of people and not enough outlets"

Cons: "Good"

Pros: "Once they were up and running, Porter was a great airline. Flight was short so i didn't expect anything fancy on the food menu anyway"
Cons: "My flight got delayed at least 5 times. Not a great first experience. Had an eerie likeliness of Spirit, which we all know is just not a real airline. not sure if I would fly again if that is the general perception of Porter airlines. I could care less about comfort as long as I get to where I am going on time, which I did not."

Pros: "Nothing"
Cons: "Everything"

Pros: "Onboard crew was very nice"
Cons: "Crew didn't answer any of my questions, were snappy, and rude."

Pros: "Polite crew"
Cons: "Would like a sandwich instead of nuts"

Pros: "Efficient"
Cons: "Late flight"

Pros: "The lounge before boarding was very diverse and qas definitely a nice treat. Info about entertainment is irrelevant since these are small planes for short distances. All in all very organized and comfortable airline."

Pros: "At least on time."
Cons: "Air craft was so old."

Cons: "Trip was cancelled within one hour of boarding"

Cons: "If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems."

Pros: "Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight."
Cons: "Louder than a usual commercial flight, probably due to being a turboprop aircraft."

Pros: "i love flying porter"

Pros: "There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays."

Pros: "Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter."

Pros: "Breakfast, bars, etcnithin"
Cons: "Nada"

Pros: "Lounge with free drinks (soda, coffee, water) and cookies/snacks! Glass drinks glasses on the plane! And leg room!"

Cons: "I fly weekly for work, but last week I got to fly to Toronto for pleasure to see my fiancé. In all of my years of traveling, I have missed a flight maybe 5 times due to traffic, weather, or other uncontrollable factors. It happened to be that on my way to Chicago Midway, there was an accident on the road that stopped traffic dead for 40 minutes. When I arrived at the airport, I begged for people to help me out by letting me cut security lines so that I wouldn't be late, but alas...others were also rushed and the TSA agents weren't too helpful. I arrived at the gate for my flight about 3 minutes late in defeat. Oh well - it happens! What was really unpleasant was that nobody would help me out. I was charged $150 to "change" my flight instead of just getting rebooked on the next one the way any other airline would happily do. And to top it all off, I was given the runaround with 3 different Porter employees diffusing responsibility. I will be moving to Toronto after the wedding but will still work out of Chicago - which means that I could provide business to Porter Airlines for the next few decades! Because of this poor service, you have lost my business. I would rather fly with another airline where customer service is a priority. Losing years of a customer's weekly business over a $150 fee seems to me to be a rather poor business model and I am sorry that the bureaucratic rules in this case could not be bent."

Cons: "The fee for my bag was too high!"

Pros: "Not sure if this is Porter Airlines or the airport, but the lounge at Billy Bishop Airport is fantastic. Free water, coffee, and snacks - it is so home-y in there, which is amazing when you are away from home :)"
Cons: "N/A"

Pros: "Departing from Billy Bishop is amazing. Incredibly quick and convenient. Complimentary nacks and drinks in the gate area?!"

Pros: "Porter lounge in Toronto"
Cons: "Nothing!"

Pros: "The service"
Cons: "The flight deleyed"

Pros: "Service. Location of both Toronto Island and Chicago Midway are closer to downtown than the bigger airports in each city."
Cons: "Porter was a nice, small, well-kept secret. Now they have expanded quite a bit and the lounge is always full, to the extent that people are sitting all over the ground. Flights are almost always late to take-off. I guess all good things must come to an end."

Pros: "Excellent. Polite service, free (and tasty) food + beverages, (dry and otherwise) comfortable seats, other customers polite, bilingual announcements, fast + efficient. Really impressed! Good price too."
Cons: "Nothing, really! No in-flight entertainment besides a magazine, but all short flights anyway."

Pros: "I took Porter many times in the past. Many delays, never major, and I found landing at city airport were convenient enough to Override the annoyance of the delays."
Cons: "This time my flight was cancelled. For no particular reasons (not due to weather). That was the only flight that was cancelled of the whole day. All other were flying. They did not say why. My guess is not enough passenger on the flight to make it worth it to fly for them. They rebooked me 24 hours later. I called customer service to ask for support and I received no support at all. I explained I was having a high risk pregnancy and was out of medication and needed to be at my DR appointment I had the next morning in Chicago. They said that there's nothing they can do. They also said additionally we also want to mention that we do not support for accomadation cost. I did not even ask but it's like they wanted to highlight that no support is given. I asked to speak to a supervisor. Told him I would like support to rebook a non Porter flight to get on time to Chicago. Again he said I am sorry we don't do that. I mentioned I was shocked that they don't even care that I was saying it was a medical reason and I asked for his name saying I will hold Porter responsible if any difficulty would happen because of this. At that point they searched for a solution. He said ok you can be on a flight but you need to board in 30 minutes. Impossible for me to do where I was but this should have been proposed to me earlier so I could have made it. And I would have done it. Second solution he gave me was to be in Ottawa boarding in 1 hour. Again impossible I was in Montreal with no car. He said you cannot hold me responsible if anything happen with your pregnancy I offered you solutions. Thank you Porter all impossible to do at the time you offered them. If you offered them all to me on time that would have maybe be possible. Anyway they made me miss 2 days of work + my doctor appointment I had to go without medication for a few days + paid for a extra hotel room. Next time I am taking air canada delta or United . I will pay more but at least I will have the guarantee to be taken in charge by their customer service if delays or cancellations happen."

Pros: "Passenger i sat next to who was also dissatisfied with Porter"
Cons: "Again, how is it possible that the board of Porter departures is about 10 flights and all ten are delayed constantly. I have never flown Porter without being delayed. Need to compensate travelers better for hours of their life they will never get back, and a 37 dollar baggage fee is absurd, not to mention a limitation of 9 kilos on a carry on."

Pros: "Entertainment n/a. My flight was really quick. We took off around 9:55pm and landed at 10:30pm which is crazy because it was supposed to be a 56min flight ! Porter makes you feel like you're in first class with their aervice. They also have a comfy lounge to wait in."
Cons: "There's no prayer or meditation room"

Cons: "As our first plane was in late, we were worried to loose this plane. But they waited for us. We arrived on time for this one."

Pros: "Excellent service, speedy process, stress free, friendly atmosphere. Felt like I was in mad men :)"

Pros: "They offered vegetable chips which were super yummy and different!"

Cons: "At the gate, we were told our plane would leave soon. An hour later, they announced the flight was cancelled and we were briskly escorted out of the terminal, told to go through customs and pick up our luggage, which had never even made it on to the plane. They were not re-booking flights at the airport, and the phone lines went to a voice mail message telling us to call back in a few days. I was stranded in Toronto with no phone and no where to stay. It's a week later and I still have not heard anything from from, even though I've called and emailed and sent snail mail."

Pros: "I enjoyed the crew, the food and the entertainment. The crew did give us peanuts for our extra 5 hours on the plane."
Cons: "We were 3 hours late for departure and took 2 extra hours in the air because of re-routing. The seats were abnormally stiff and went back so little that it was extremely hard to fall asleep during the 18 hours we were on board. The crew was unwillng to let us bring our instruments on board and thus, they cracked from the air pressure during the flight."

Pros: "Service flight on time food"
Cons: "No movies for 7 hour flight"

Pros: "Low fare"
Cons: "Flight delayed initially due to weather. When weather cleared flight delayed half hour because they could not find the pilot."

Pros: "Departure was orderly and staff interactions good"

Pros: "Boarding was good, but pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!"
Cons: "Pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!"

Cons: "no entertainment and poor seat selection"

Pros: "Love the individual entertainment & the friendly staff team"

Pros: "The flight attendant was very nice and smiling."

Pros: "$800 reimbursement 1st class"
Cons: "They overbooked the flight by 2 passengers."

Cons: "I did not fly to Montreal and I did not catch flight to Barcelona I am fling again tonight Toronto - Barcelona direct"

Pros: "service on the plane was good and the crew was very nice to be patient while we boarded the plane with 3 little kids"

Cons: "I arrived at the gate and looked at my ticket to see "GTE" where the seat number usually is. I was informed upon arriving at the desk at the gate that that meant Air Canada has also decided to participate in the ridiculous practice of overbooking their flights and that even though I purchased my ticket roughly 8 weeks prior, there was a chance I might miss my flight to my friend's WEDDING. The lady who was working the desk was as unhelpful and dismissive as you could possibly imagine, refusing to look at me and giving me attitude for merely waiting in the area to see if anyone had missed the flight so I could get on. It was surreal; the only way I could describe her incomprehensible behavior would be to say it was as if her boss were right in front of her and she was trying her damnedest to get fired. It was one of those situations where you could tell this miserable, miserable person was enjoying the power trip she was on and doing everything in her power to make me feel helpless and angry. I made my flight, miraculously, but it was the worst customer service experience I have ever had in my life, airport or not."

Pros: "Professional fight attendants, very nice."
Cons: "The flight took off late but most of the lost time was made up during the flight time."

Pros: "Again, ground crew took good care of me and saw me to the baggage pick-up. You have lovely staff."

Pros: "I paid a nominal fee to get an exit row. I have a perpetually sore hip and I had a pain-free flight."

Cons: "First flight was canceled, they did not get me on a flight till 4 pm the next day! Not to mention the two French Canadians I talked to were extremely rude. Finally the 3rd customer service women tried to get me home sooner but was unable to!! Have flown for years on air Canada without issues but this last trip was such an inconvenience I will not being flying with them agin!! They also did not cover my hotel or the taxi costs associated with me having my flight canceled, not even a discount!!!!!"

Cons: "Flight was late so I missed my connection. Then my luggage was delayed by five hours behind me. Generally poor service."

Pros: "The entertainment offerings were good. One crew member in particular helped us get back on the flight after we had been booted."
Cons: "Gate agent for Air Canada completely unhelpful about getting us to our connecting flight. Then the Toronto Airport was just HORRIBLE: all along the way, we had to go through security again to get to the American side, and there was no warning that the drinks we had bought *at the Dublin airport* would all be thrown out. Rude security employees. They also very slowly went through the duty free bottles of whisky I bought *at the Dublin airport*. Then there was this stupid line of kiosks that no one knew how to use, then for some reason another boarding check, then another, and then finally customs, with more rude staff members. We had NO IDEA any of this was coming, and got no warning from Air Canada. Then we rushed to our connecting flight, only to find out that we had been booted from the flight anyway. (I got an email about it, which of course I didn't check because I have limited data -- not everyone is made of money who can afford unlimited data!) Then we got on finally boarded, only to sit on the tarmac forever in uncomfortable seats when they could've just let us sit in the airport. Ugh."

Pros: "The flight last less time than expected."

Pros: "Nice staff"
Cons: "Not much"

Pros: "Flight was good but there was no tv"
Cons: "There was no TV or to play games"

Pros: "Everything went smoothly. The crew was fabulous and the flight smooth."
Cons: "Not a single complaint from me!"

Cons: "The fact that my ticket said something different from my itinerary and I spent far too long at the counter to get a seat assignment."

Cons: "Flight delayed, service with discrimination, pride, specially male crew, this is a really bad flight experience."

Cons: "It was so late, I almost missed my connecting flight. They were not helpful. They did not communicate well and they refused to take any responsibility."

Cons: "Very bad cabin pressure -- lots of ear pain."

Pros: "Again, nice selection of entertainment and great crew."

Cons: "There was some dripping from the ceiling on those of us in the back of the plane. It might have been condensation from the air conditioning or air flow nozzles. In the groove of the ceiling immediately over the seats there seemed to be some dirt or mold."

Pros: "Not much can go wrong on a flight shorter than 90 minutes."
Cons: "3 delays that added up to 1 hr, but counter personnel kept us informed."

Pros: "I . was impressed with the food and service.over all the whole trip was very good"
Cons: "there was nothing I did not like"

Cons: "Moving through security and customs in the Toronto airport was incredibly slow, with 4 or 5 checkpoints, all with lines. Staff were polite but there were not enough of them. We almost missed our connecting flight, and our bags apparently did miss it, because they have not yet arrived in Chicago (see previous comments). Air Canada should have seen the problem in terms of timing with the connecting flight and expedited better. Will try to avoid Air Canada in the future, especially if there are connections in Toronto."

Pros: "All went smoothly"

Pros: "Nothing"
Cons: "first flight cancelled, second flight delayed so impossible to get the connection. Nobody called me about it, I had to go to ask."

Cons: "if you get in a que, then the computer goes down , your dead, AC line will be 1.5 hours to get to rebook. then you have 2 day to stay before you can get out. if you decide to go on delta because staying 2 day in hotel is more expensive than buying a new ticket ac will not refund you. Air Canada is the least flexible airline in the world relative to refund."

Pros: "Tv in all seats, individual air controls, the crew was nice and I offered up my bag to go on the checked bags when asked and it was the first one out on the bagged claim"
Cons: "I'm 5'8 and my legs hardly fit when sitting straight in the seat"

Pros: "was forced to spend the night in Toronto because Air Canada didn't seem to know that there would be a huge crowd at the airport that evening. I was told as I exited my flight that I would not make the connecting flight and I had to spend the night in Toronto. I will never fly Air Canada again"

Pros: "The crew members in both the flights were amazing. they seemed like they enjoyed their job. Its not very common at Air Canada."
Cons: "The flight from Chicago to Toronto was delayed by half hour. But the boarding gate agents did not even mention the delay."

Cons: "after wetting half hour in the line they said i didn't pay for my ticket and tell me to parches a new ticket"

Pros: "It was comfy. Individual screen."
Cons: "We took off 25 minutes late and no food was served, not even a snack. I had to pay 25$ to check in my suitcase."

Cons: "Flight was late"

Pros: "Run by united but more efficient than a recent Air Canada flight."
Cons: "3 hour flight and had to pay extra for entertainment. Only two biscuits given for food. Cramped seats for anyone 6ft tall."

Cons: "I could not check in online for both legs of the flight. Stuck in the middle seat even though I was ready to check in 24 hrs prior."

Pros: "Overall it was good. The crew was very friendly. The plane was small and it was a short flight, so everything else was average as expected for a short flight."

Pros: "The crew was good and the in-flight entertainment options were decent."
Cons: "Plane took forever to take off because we were waiting for people late from layovers. Got one drink, no snacks, nothing else. Plane arrived over an hour late."

Cons: "It was a United flight and everywhere it said it was Air Canada instead of United. Hopping terminals and running through them last minute is not fun. To top it off the flight got delayed a ton of times and messed up our schedules completely."

Pros: "Everithing-----Ramesh"
Cons: "Ramesh"

Cons: "delayed 2-3 hours in Vancouver so missed connection, had to rent a vehicle to get home. Everytime, United into O'Hare… never again!"

Pros: "Cancellation came with a new flight and coucher for sleeping overnight at a O'Hare Hotel which was very well organized and went smoothly. Staff at ORD were waiting for us and very helpful."
Cons: "Was unable to check in my Air Canada flight the day before to find out the next day, at the airport that the flight was cancelled. The Air Canada flight was operated by United and no such information was provided in my reservation on Kayak or at the Air Canada counter in SAN airport, so I had to guess that another Star Alliance member would be taking over."

Cons: "Gate was changed after check-in, but lack of announcements nearly caused my 84 year old mother to miss her flight, which was changed from gate 80 to 62."

Read more about Porter Airlines
COVID-19 information

Safety measures for airlines flying from Toronto Island to Chicago

Airlines flying from Toronto Island to Chicago have enacted additional safety measures and adjusted policies to better accommodate travellers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Toronto Island to Chicago

Mandatory masks

Masks required on board, masks provided on flights from Toronto Island to Chicago

Social distancing seating

Middle seats unavailable to book on flights from Toronto Island to Chicago

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Toronto Island to Chicago

Book cheap flights from Toronto Island to Chicago

Recent round-trip flight deals

12/7
Mon.
direct
Porter Airlines
1h 47m
YTZ - MDW
26/7
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1h 42m
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8h 24m
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8h 31m
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4h 25m
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1h 47m
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1h 42m
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Air Canada
5h 26m
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5h 15m
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1h 47m
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1h 42m
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5h 45m
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Porter Airlines
1h 47m
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1h 42m
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29/3
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Porter Airlines
1h 50m
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29/3
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Air Canada
8h 18m
YTZ - ORD
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23h 39m
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