Find Cheap Flights from Chicago Midway to Toronto Island (MDW - YTZ)

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Fri 15/12
Fri 22/12
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Good to Know

Average price:
C$ 452
(avg. price over the last 2 weeks)
Good Deal:
C$ 316
or less (round trip)

When to Book Flights from Chicago Midway to Toronto Island

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$ 315 or less.
The cheapest flight from Chicago Midway to Toronto Island was found, on average, 85 days before departure.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 11% 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 Chicago Midway to Toronto Island Flights

How long does a flight from Chicago Midway to Toronto Island take?
An average nonstop flight takes 1h 37m, covering a distance of 713 km.
How many flights are there between Chicago Midway and Toronto Island?
There are 74 (nonstop) flights between Chicago Midway and Toronto Island per week, averaging 11 per day.
Which airlines provide the cheapest flights from Chicago Midway to Toronto Island?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines (C$ 267)
Do I need a passport to fly between Chicago Midway and Toronto Island?
Yes.
Which airlines fly most frequently between Chicago Midway and Toronto Island?
Porter Airlines (10 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from Chicago Midway to Toronto Island?
For Chicago Midway to Toronto Island, Friday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Toronto Island back to Chicago Midway, the best deals are generally found on Thursday, with Tuesday being the most expensive.

Book cheap flights from Chicago Midway to Toronto Island (round-trip)

Airports
Origin
Chicago
C$ 267
only
C$ 267
Destination
Toronto
C$ 267
only
C$ 267
Fri, 13 Apr
MDW
YTZ
1h 40m
Tue, 17 Apr
YTZ
MDW
1h 45m
C$ 267
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 10.0

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.

MDW
YTZ
Okay 5.6

Nice crew, snacks and drinks, good price, calm experience.

All flights delayed by 1 hour. Maybe equipment logistics could be better.

MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Mediocre 2.0

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

MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

Fri, 2 Feb
MDW
YTZ
1h 40m
Mon, 5 Feb
YTZ
MDW
1h 50m
C$ 272
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 5 Jan
MDW
YTZ
1h 37m
Sun, 7 Jan
YTZ
MDW
1h 50m
C$ 270
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Mediocre 2.0

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

MDW
YTZ
Okay 4.0

Staff was nice everywhere during this trip.

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!

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

Thu, 8 Feb
MDW
YTZ
1h 37m
Sun, 11 Feb
YTZ
MDW
1h 50m
C$ 283
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Mediocre 2.0

Literally nothing. Even the free beer and wine didn't make up for this company!!

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!!!!

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

Thu, 1 Mar
MDW
YTZ
1h 37m
Sun, 4 Mar
YTZ
MDW
1h 50m
C$ 283
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

MDW
YTZ
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

Mon, 19 Mar
MDW
YTZ
1h 37m
Fri, 23 Mar
YTZ
MDW
1h 50m
C$ 283
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

MDW
YTZ
Excellent 10.0

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.

MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Mediocre 2.0

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

Fri, 27 Apr
MDW
YTZ
1h 40m
Sun, 29 Apr
YTZ
MDW
1h 45m
C$ 283
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 10.0

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.

MDW
YTZ
Okay 5.6

Nice crew, snacks and drinks, good price, calm experience.

All flights delayed by 1 hour. Maybe equipment logistics could be better.

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Mediocre 2.0

Literally nothing. Even the free beer and wine didn't make up for this company!!

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!!!!

Fri, 12 Jan
MDW
YTZ
1h 37m
Mon, 15 Jan
YTZ
MDW
1h 50m
C$ 294
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Okay 5.6

Nice crew, snacks and drinks, good price, calm experience.

All flights delayed by 1 hour. Maybe equipment logistics could be better.

Thu, 15 Mar
MDW
YTZ
1h 37m
Thu, 22 Mar
YTZ
MDW
1h 50m
C$ 294
Trip: 8 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Mediocre 2.0

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

MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Excellent 8.6

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.

Baggage rules seemed to be enforced arbitrarily... gate Checking was routine... but I was forced to pay to check a bag.

Wed, 27 Dec
MDW
YTZ
1h 37m
Thu, 4 Jan
YTZ
MDW
1h 50m
C$ 305
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

MDW
YTZ
Excellent 8.6

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.

Baggage rules seemed to be enforced arbitrarily... gate Checking was routine... but I was forced to pay to check a bag.

MDW
YTZ
Mediocre 2.0

Literally nothing. Even the free beer and wine didn't make up for this company!!

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!!!!

Thu, 28 Dec
MDW
YTZ
1h 37m
Tue, 2 Jan
YTZ
MDW
1h 50m
C$ 307
Trip: 6 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

MDW
YTZ
Okay 4.0

Staff was nice everywhere during this trip.

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!

MDW
YTZ
Excellent 10.0

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.

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

Fri, 4 May
MDW
YTZ
1h 40m
Sun, 6 May
YTZ
MDW
1h 45m
C$ 307
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Mediocre 2.0

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

MDW
YTZ
Excellent 8.6

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.

Baggage rules seemed to be enforced arbitrarily... gate Checking was routine... but I was forced to pay to check a bag.

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Mediocre 2.0

They were not organized. Delayed every flight and cancelled two flights and offered no complemsation. I thought there'd be better customer service.

MDW
YTZ
Excellent 10.0

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.

Mon, 4 Jun
MDW
YTZ
1h 39m
Wed, 6 Jun
YTZ
MDW
1h 45m
C$ 307
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 86 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Mediocre 2.0

Literally nothing. Even the free beer and wine didn't make up for this company!!

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!!!!

MDW
YTZ
Excellent 10.0

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.

MDW
YTZ
Excellent 8.6

Snacks and the complimentary wines

Flight attendant did not allow earbud headphone during landing. I have not seen this in other airlines.

MDW
YTZ
Okay 5.6

Nice crew, snacks and drinks, good price, calm experience.

All flights delayed by 1 hour. Maybe equipment logistics could be better.

MDW
YTZ
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.