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

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Good to Know

Average price:
C$ 351
(avg. price over the last 2 weeks)
Good Deal:
C$ 302
or less (round trip)

When to Book Flights from Chicago 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$ 302 or less.
The cheapest flight from Chicago to Toronto Island was found, on average, 87 days before departure.
Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 30% 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 to Toronto Island Flights

How long does a flight from Chicago to Toronto Island take?
An average nonstop flight takes 1h 37m, covering a distance of 698 km.
How many flights are there between Chicago and Toronto Island?
There are 46 (nonstop) flights between Chicago and Toronto Island per week, averaging 6 per day.
Which airlines provide the cheapest flights from Chicago to Toronto Island?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines (C$ 287) and Multiple Airlines (C$ 495)
Do I need a passport to fly between Chicago and Toronto Island?
Yes.
Which airlines fly most frequently between Chicago 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 from Chicago to Toronto Island?
For Chicago to Toronto Island, Wednesday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Toronto Island back to Chicago, the best deals are generally found on Thursday, with Friday being the most expensive.

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

Airports
Origin
Chicago
C$ 495
only
C$ 495
C$ 274
only
C$ 274
Destination
Toronto
C$ 274
only
C$ 274
Wed, 21 Mar
MDW
YTZ
1h 37m
Sat, 24 Mar
YTZ
MDW
1h 50m
C$ 274
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 26 Apr
MDW
YTZ
1h 40m
Sun, 29 Apr
YTZ
MDW
1h 45m
C$ 287
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 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
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

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, 1 Mar
ORD
YTZ
5h 47m
Sat, 3 Mar
YTZ
ORD
8h 13m
C$ 495
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Tue, 1 May
MDW
YTZ
1h 40m
Sat, 5 May
YTZ
MDW
1h 45m
C$ 287
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
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
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
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

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

Wed, 6 Jun
MDW
YTZ
1h 40m
Tue, 12 Jun
YTZ
MDW
1h 45m
C$ 287
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
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

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

Comfy large seats. Great service

Little slow to leave

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

Fri, 9 Mar
MDW
YTZ
1h 37m
Sun, 11 Mar
YTZ
MDW
1h 50m
C$ 290
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 8.6

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 8.6

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
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

Wed, 23 May
MDW
YTZ
1h 40m
Sun, 3 Jun
YTZ
MDW
1h 45m
C$ 290
Trip: 12 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
Good 7.6

The flight attendants were very nice. Timely boarding.

Very small plane with only one bathroom.

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.

Tue, 24 Jul
MDW
YTZ
1h 45m
Tue, 31 Jul
YTZ
MDW
1h 45m
C$ 327
Trip: 8 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

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 10.0

Nice flight

Highly recommend it

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
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.

Tue, 24 Jul
ORD
YTZ
6h 50m
Wed, 1 Aug
YTZ
ORD
6h 29m
C$ 516
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Tue, 31 Jul
MDW
YTZ
1h 40m
Sun, 19 Aug
YTZ
MDW
1h 45m
C$ 327
Trip: 20 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
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 9.6

Comfy large seats. Great service

Little slow to leave

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.

Wed, 6 Jun
ORD
YTZ
6h 42m
Sat, 16 Jun
YTZ
ORD
7h 55m
C$ 521
Trip: 11 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 3 Aug
MDW
YTZ
1h 40m
Mon, 6 Aug
YTZ
MDW
1h 45m
C$ 327
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 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 10.0

Nice flight

Highly recommend it

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!!!!

Tue, 7 Aug
ORD
YTZ
6h 50m
Tue, 14 Aug
YTZ
ORD
7h 10m
C$ 550
Trip: 8 days
Overall 0.0 Poor
Based on 0 reviews
Fri, 3 Aug
MDW
YTZ
1h 40m
Mon, 6 Aug
YTZ
MDW
1h 45m
C$ 356
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 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
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.

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.

Thu, 9 Aug
ORD
YTZ
6h 15m
Sun, 12 Aug
YTZ
ORD
7h 56m
C$ 553
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sun, 18 Mar
MDW
YTZ
1h 37m
Sat, 24 Mar
YTZ
MDW
1h 50m
C$ 357
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
Excellent 8.0

Delay

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 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

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.

Fri, 23 Feb
MDW
YTZ
1h 37m
Sun, 25 Mar
YTZ
MDW
1h 50m
C$ 361
Trip: 30 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

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
Excellent 8.0

Delay

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.

Fri, 1 Jun
ORD
YTZ
6h 32m
Tue, 5 Jun
YTZ
ORD
8h 23m
C$ 597
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Tue, 3 Apr
ORD
YTZ
5h 57m
Sat, 7 Apr
YTZ
ORD
8h 13m
C$ 630
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sun, 25 Feb
MDW
YTZ
1h 37m
Mon, 26 Feb
YTZ
MDW
1h 50m
C$ 421
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
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
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

MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

Show more results

Chicago to Toronto Island Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Toronto Island
Flights Depart from Chicago
Flight Price C$ 274
Distance 698 km
Airlines Major Airline, Porter Airlines
*
Prices are per person, are for e–tickets and include all taxes & fees in CAD.

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Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
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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.