MDW - YTZ

Find cheap flights from Chicago Midway Airport to Toronto Island

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MDW — YTZ
20 Jan — 27 Jan1
Return
1 adult
Economy
0 bags
From?
To?
Thu 20/1
Thu 27/1

Good to know

Low season

April

High season

July

Average price round-trip

C$ 303
Best time to beat the crowds (23% less expensive on average)
Most popular time to fly (23% more expensive on average)
(avg. price over the last 2 weeks)

When to book flights from Chicago Midway Airport to Toronto Island

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

Top tips for finding a cheap flight

  • High season is considered to be June, July and August. The cheapest month to fly is April.
  • Morning departure is around 33% more expensive 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 Chicago Midway Airport to Toronto Island flights

Top airline flying Chicago Midway to Toronto Island

Scores according to KAYAK customer reviews
7.7
Porter AirlinesOverall score based on 2726 reviews
7.8Boarding
7.8Comfort
8.3Crew
6.8Entertainment
7.8Food
Airline reviews

Flight delays both going and return flights

Read more about Porter Airlines

Flight delays both going and return flights

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: "Efficient, punctual, polite and reliable"
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."
Cons: "Delay"
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: "Nothing"
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."
Cons: "NA"
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: "A flight is a flight"
Cons: "Flirght was delayed because of weather, fine. We learn about the delay after the time for departure was passed . Initially a fifteen min delay become 30. No communications, everyone standing in line until we are called to board by a teenager . It was too icy to get on the tarmack so we got to stay in a damp corridor until they clear the way. When we got in the plane , after some wait we are told the plane need de-icing. It took one hour before they finally got it done. All this time the Porter web site was useless. It even said we departed. All the aggravation could have been avoided if Porter would be more transparent about their delay and had better ground coordination with the airport personnel"
Pros: "The service and the crew,."
Cons: "The connecting flight was delayed by 1h30 ."
Cons: "Flights were delayed both directions"
Pros: "없음"
Cons: "비행기 지연, 4시간 30분 기다림. 예정 도착시간보다 5시간 늦게 도착"
Cons: "None"
Pros: "Everything was good."
Pros: "Very friendly staff Free drinks (wine, beer, vodka coolers) in flight Easy small airport terminal at Billy Bishop Airport Very fast through immigration and customs"
Cons: "Policy that cannot standby got earlier flight - especially if later flight is already listed as delayed This is to force paying $150 fee, not customer friendly."
COVID-19 information

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

Airlines flying from Chicago Midway Airport to Toronto Island 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 Chicago Midway Airport to Toronto Island

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Flexible cancellations

Waiving of change fees. Search flexible flights from Chicago Midway Airport to Toronto Island

Book cheap flights from Chicago Midway Airport to Toronto Island

Recent round-trip flight deals

12/3Sat
directPorter Airlines
1h 37mMDW-YTZ
15/3Tue
directPorter Airlines
1h 50mYTZ-MDW
C$ 275
10/2Thu
directPorter Airlines
1h 37mMDW-YTZ
13/2Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 278
29/4Fri
directPorter Airlines
1h 37mMDW-YTZ
2/5Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 279
16/4Sat
directPorter Airlines
1h 37mMDW-YTZ
2/5Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 280
27/5Fri
directPorter Airlines
1h 37mMDW-YTZ
29/5Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 285
1/5Sun
directPorter Airlines
1h 37mMDW-YTZ
8/5Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 287
6/5Fri
directPorter Airlines
1h 37mMDW-YTZ
9/5Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 289
2/6Thu
directPorter Airlines
1h 42mMDW-YTZ
6/6Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 295
26/3Sat
directPorter Airlines
1h 37mMDW-YTZ
1/4Fri
directPorter Airlines
1h 50mYTZ-MDW
C$ 297
11/3Fri
directPorter Airlines
1h 37mMDW-YTZ
21/3Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 298
16/2Wed
directPorter Airlines
1h 37mMDW-YTZ
23/2Wed
directPorter Airlines
1h 50mYTZ-MDW
C$ 299
2/5Mon
directPorter Airlines
1h 37mMDW-YTZ
17/5Tue
directPorter Airlines
1h 50mYTZ-MDW
C$ 308
17/5Tue
directPorter Airlines
1h 37mMDW-YTZ
26/5Thu
directPorter Airlines
1h 50mYTZ-MDW
C$ 309
18/2Fri
directPorter Airlines
1h 37mMDW-YTZ
25/2Fri
directPorter Airlines
1h 50mYTZ-MDW
C$ 318
16/3Wed
directPorter Airlines
1h 37mMDW-YTZ
13/4Wed
directPorter Airlines
1h 50mYTZ-MDW
C$ 319
18/5Wed
directPorter Airlines
1h 37mMDW-YTZ
20/8Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 320
16/3Wed
directPorter Airlines
1h 37mMDW-YTZ
16/4Sat
directPorter Airlines
1h 50mYTZ-MDW
C$ 323
16/5Mon
directPorter Airlines
1h 37mMDW-YTZ
25/5Wed
directPorter Airlines
1h 50mYTZ-MDW
C$ 330
27/6Mon
directPorter Airlines
1h 42mMDW-YTZ
2/7Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 332
22/3Tue
directMultiple Airlines
1h 37mMDW-YTZ
27/3Sun
2 stopsMultiple Airlines
17h 48mYTZ-MDW
C$ 411

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Recent one-way flight deals

11/2Fri
directPorter Airlines
1h 37mMDW-YTZ
C$ 119
4/3Fri
directPorter Airlines
1h 37mMDW-YTZ
C$ 120
15/2Tue
directPorter Airlines
1h 37mMDW-YTZ
C$ 123
10/5Tue
directPorter Airlines
1h 37mMDW-YTZ
C$ 124
3/5Tue
directPorter Airlines
1h 37mMDW-YTZ
C$ 125
10/2Thu
directPorter Airlines
1h 37mMDW-YTZ
C$ 131
18/2Fri
directPorter Airlines
1h 37mMDW-YTZ
C$ 143
4/7Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 174
12/7Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 176
17/5Tue
directPorter Airlines
1h 37mMDW-YTZ
C$ 181
2/7Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 185
24/1Mon
directPorter Airlines
1h 37mMDW-YTZ
C$ 213
30/1Sun
directPorter Airlines
1h 37mMDW-YTZ
C$ 214
3/2Thu
directPorter Airlines
1h 37mMDW-YTZ
C$ 222
25/1Tue
directPorter Airlines
1h 37mMDW-YTZ
C$ 233
18/3Fri
2 stopsMultiple Airlines
23h 22mMDW-YTZ
C$ 257
4/3Fri
3 stopsMultiple Airlines
43h 31mMDW-YTZ
C$ 295
4/3Fri
3 stopsMultiple Airlines
43h 31mMDW-YTZ
C$ 297
18/3Fri
3 stopsMultiple Airlines
28h 21mMDW-YTZ
C$ 418
29/1Sat
3 stopsMultiple Airlines
41h 54mMDW-YTZ
C$ 544

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Chicago Midway Airport - Toronto Island Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Toronto Island (YTZ)Canada

Return flight deals:

Toronto Island - Chicago Midway Airport

Cabin classes:

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