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

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Sat 2/24
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Good to Know

Average Price:
$300
(avg. price over the last 2 weeks)
Good Deal:
$224
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 $223 or less.
The cheapest flight from Chicago Midway to Toronto Island was found 85 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 4% 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 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 443 miles.
How many flights are there between Chicago Midway and Toronto Island?
There are 46 (nonstop) flights between Chicago Midway and Toronto Island per week, averaging 6 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 ($230)
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 (6 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Toronto Island?
For Chicago Midway to Toronto Island, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from Toronto Island back to Chicago Midway, the best deals are generally found on Thursday, with Thursday being the most expensive.

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

Airports
Origin
Chicago
$216
only
$216
Destination
Toronto
$216
only
$216
Sat, Mar 31
MDW
YTZ
1h 37m
Sun, Apr 1
YTZ
MDW
1h 50m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Mon, Mar 26
MDW
YTZ
1h 37m
Sun, Apr 1
YTZ
MDW
1h 50m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

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!

Wed, Mar 21
MDW
YTZ
1h 37m
Sat, Mar 24
YTZ
MDW
1h 50m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Mar 29
MDW
YTZ
1h 37m
Tue, Apr 3
YTZ
MDW
1h 50m
Trip: 6 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 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
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

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 8.0

Delay

Sun, Mar 18
MDW
YTZ
1h 37m
Sat, Mar 24
YTZ
MDW
1h 50m
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 30
MDW
YTZ
1h 37m
Tue, Apr 3
YTZ
MDW
1h 50m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 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 8.0

Delay

MDW
YTZ
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

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, Mar 23
MDW
YTZ
1h 37m
Wed, Mar 28
YTZ
MDW
1h 50m
Trip: 6 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Apr 5
MDW
YTZ
1h 40m
Sun, Apr 8
YTZ
MDW
1h 50m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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 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 8.0

Delay

Thu, Jul 12
MDW
YTZ
1h 40m
Sun, Jul 15
YTZ
MDW
1h 45m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Apr 6
MDW
YTZ
1h 37m
Sun, Apr 8
YTZ
MDW
1h 50m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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.

MDW
YTZ
Excellent 8.0

Delay

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.

Fri, Apr 13
MDW
YTZ
1h 40m
Mon, Apr 16
YTZ
MDW
1h 45m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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.

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 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
Okay 5.6

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

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

Sat, Apr 14
MDW
YTZ
1h 40m
Mon, Apr 16
YTZ
MDW
1h 45m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

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
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

it was such a smooth flight

all good

Mon, Apr 16
MDW
YTZ
1h 40m
Wed, Apr 18
YTZ
MDW
1h 45m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 8.0

Delay

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 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
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, Apr 19
MDW
YTZ
1h 40m
Mon, Apr 23
YTZ
MDW
1h 45m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

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

Nice flight

Highly recommend it

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
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!

Fri, Apr 20
MDW
YTZ
1h 40m
Sun, Apr 22
YTZ
MDW
1h 45m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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 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

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
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

Sat, Apr 21
MDW
YTZ
1h 40m
Fri, Apr 27
YTZ
MDW
1h 45m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

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

Wed, Apr 25
MDW
YTZ
1h 40m
Thu, Apr 26
YTZ
MDW
1h 45m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 8.0

Delay

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 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 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

Thu, Apr 26
MDW
YTZ
1h 40m
Mon, Apr 30
YTZ
MDW
1h 45m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

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
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

Nice flight

Highly recommend it

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.

Tue, May 1
MDW
YTZ
1h 40m
Sat, May 5
YTZ
MDW
1h 45m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

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 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
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!

Thu, May 3
MDW
YTZ
1h 40m
Sat, May 5
YTZ
MDW
1h 45m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 88 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

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 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 10.0

Nice flight

Highly recommend it

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!!!!

Show more results

Chicago Midway to Toronto Island Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Toronto Island
Flights Depart from Chicago Midway
Flight Price $216
Distance 443 miles
Airlines Major Airline, Porter Airlines
*
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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.