Find cheap flights from Toronto Island to Chicago Midway Airport

YTZ - MDW

Find cheap flights from Toronto Island to Chicago Midway Airport

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport. Bundle your flight + hotel and save!

Round-trip
Economy
Toronto (YTZ)
Chicago Midway
Thu 12/9
Thu 12/16
Any month
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Good to know

Low season

November

High season

May

Average price round-trip

$248
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 20% increase in price.
(avg. price over the last 2 weeks)

When to book flights from Toronto Island to Chicago Midway Airport

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight

  • The cheapest flight from Toronto Island to Chicago Midway Airport was found 30 days before departure, on average.
  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be April, May and June. The cheapest month to fly is November.
  • Morning departure is around 27% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Toronto Island to Chicago Midway Airport flights

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Top airline flying Toronto Island to Chicago Midway

Scores according to KAYAK customer reviews

7.7
Porter Airlines
Overall score based on 2,720 reviews
7.8
Boarding
7.8
Comfort
8.3
Crew
6.8
Entertainment
7.8
Food
Airline reviews

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: "N/A"
Cons: "Same as previous answer, but due to cancellation of earlier flight and our connection being delayed, ended up not landing in Newark until about 10pm when we originally should've landed in around 3. This caused us to miss a Broadway show we had bought tickets for ($150/ticket) as well as lost out on dinner reservations we had made. We then had to take an Uber as our friends could not pick us up at that time (a further $80). My son had taken off three days from work and we lost most of the first one due to Porter's incompetence. Their only comment was that they weren't obliged to do anything for us because we had booked through an agent and not directly with Porter."

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: "Landing at Billy Bishop is very convenient."
Cons: "20 minutes delay on the incoming first flight, 35 minutes on the out coming flight. Our organization sent 100 persons to an event in Toronto this weekend. Some colleagues that had a 2 pm flight were told that they would leave by the 10 pm flight. Our flight eas already delayed, the door had been already closed, but it was reopened so that a passenger, who had arrived last, could go back to the lounge to pickup some fhat he had forgotten. Porter has become a very unreliable company. Like some of my colleagues, I will now consider flying out of Pearson airport sadly."

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."

Pros: "Efficient, punctual, polite and reliable"

Pros: "The service is very good. In flight snacks and drinks are complimentary."
Cons: "No in flight entertainment."

Cons: "Flight was delayed by 3 hours."

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: "fast"
Cons: "no TSA precheck"

Cons: "I mistakenly bought a ticket on the wrong date. I tried to change it but with their $200 change policy, it was cheaper to buy a new one. Regretfully, I bought it with Porter again, only because it was the cheapest available and I was already out a lot of money. It had to be a later flight, and people were waiting for me in Ottawa for a wedding party. The flight seemed like it was on time, but instead of getting us there, they made us sit on the plane for 45 minutes to wait for other passengers coming from another flight. I would consider a few minutes nice and the right thing to do, but not 45, as this was a complete disregard for the rest of us. They said it was the last flight to Halifax. Great, that lets me know they just didn't want to put them up in a hotel. They have ridiculously high fees, but they won't deliver the service promised in a timely manner to save themselves money. Seems like they are pinching pennies at the cost of quality service."

Cons: "The flights were cancelled after everyone was already waiting for a long time for their delayed flights. Then the rebooking process took way too long after the staff at the airport said it would take 20 minutes. The website is extremely confusing about which flight you are rebooked, confirmed or on standby. After waiting at the airport for five hours, I still ended up having to spend the night in Toronto. I flew back the next day after my flight was rebooked four times... I filed a claim for hotel reimbursement, but no responses after three days...."

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

Cons: "Good"

Pros: "Nothing"
Cons: "Everything"

Pros: "My past 4 Porter flights over a few months have had at least 40 minutes of delays. They all also had the annoying pattern of announcing that the delay would be extended a few times, then saying no more delays, then not boarding until after the newest departure time while claiming no more delays. Toronto airport is cute but wifi is pretty bad and hasn't worked at all a few times. Recently gate area has been ridiculously overcrowded, people sitting all over the floor. Free food/drinks is nice but still very limited options and unsurprisingly people make a big mess of the free food area. Overall I prefer a large clean airports where wifi always works well and you can always find a seat for the 30+ minutes you wait for your flight."
Cons: "Wifi Crowded gate Delays Bad communication/dishonesty about delays"

Pros: "Nothing"
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: "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: "Small airport. Easy to find everything. Ferry ride fun. Staff did not seem happy to be at work nor did they smile or acknowledge me. I asked 2 staff questions and was barked at: red line! And was told to get into a line that was non existent outside of security."
Cons: "I asked if I was supposed to leave my luggage in the rack that was just outside of the plane because I saw that's what everyone was doing. I was told it was my choice but that if it didn't fit in the overhead I would have to come back out and put it on the rack. I was very dismayed when I got off the plane to see that I had to wait in the hallway for quite a while until my luggage appeared. It was a real traffic jam of people. I really wish I had put my luggage in the overhead. Also, minutes before boarding we were told to go and verify our passports. It was quite a rush to run to the other end of the room, wait in line and then get to the boarding gate. I barely made it back in time even though I had been waiting there for nearly an hour ."

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: "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: "Specifically purchased a $350 USD one way ticket with 2 1/2 hr travel time from Montreal to Windsor with a 30 min layover in Toronto, After landing in Toronto, same plane flies to Windsor once some passengers de-board and others board. There were only a 6 or 7 passengers left on the plane after landing in Toronto and in 5 min Porter announced that they are cancelling the flight without giving a reason. The actual reason is there was not enough passengers to make it worth for them to fly plane to Windsor, so gave us the option to be booked on the next flight in 3hrs or the following in 6hrs. Issued a $50 CAN voucher (good for 6 month on Prorter) for the inconvenience and a $10 meal credit. NOT really a good deal, as they value your time at $20 per hour in voucher credits, but charged $350 for the ticket in real money. No representatives there can help in any other way or offer anything other than the $50 voucher. Just sit and wait in an overcrowded lounge. The flight to Windsor 3 hrs later was completely full,"

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"

Cons: "Porter lost my baggage despite such a short and easy flight for them to track. Let's see how long they take to get the luggage back to me in what condition"

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."

Read more about Porter Airlines
COVID-19 information

Safety measures for airlines flying from Toronto Island to Chicago Midway Airport

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

Heightened sanitation

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

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from Toronto Island to Chicago Midway Airport

Recent round-trip flight deals

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