Trips

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

Search hundreds of travel sites at once for deals on flights to Toronto Island

Depart
Return
Any month
Compare vs. KAYAK |

Chicago to Toronto Island Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Toronto Island
Flights Depart from Chicago
Flight Price C$ 275
Distance 699 km
Airlines Major Airline, Porter Airlines

Good to Know

Good Deal:
C$ 287
or less round-trip within
4 months
of travel is a good deal

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

The cheapest flight from Chicago to Toronto Island was found, on average, 89 days before departure.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 15% 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 35m, covering a distance of 698 km.
How many flights are there between Chicago and Toronto Island?
There are 88 (nonstop) flights between Chicago and Toronto Island per week, averaging 13 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$ 279) and Multiple Airlines (C$ 491)
Which airlines fly most frequently between Chicago and Toronto Island?
Porter Airlines (12 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, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Toronto Island back to Chicago, the best deals are generally found on Wednesday, with Saturday being the most expensive.

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

Airports
Origin
Chicago
C$ 491
only
C$ 491
C$ 275
only
C$ 275
Destination
Toronto
C$ 275
only
C$ 275
Tue, 18 Dec
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
Thu, 3 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 275
Trip: 17 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 18 Oct
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Sun, 28 Oct
YTZ
Toronto Island
MDW
Chicago Midway
1h 45m
C$ 279
Trip: 11 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
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

MDW
YTZ
Excellent 10.0

Service of crew and snacks

MDW
YTZ
Excellent 8.0

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

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

Fri, 9 Nov
ORD
Chicago O'Hare International
YTZ
Toronto Island
9h 14m
Mon, 12 Nov
YTZ
Toronto Island
ORD
Chicago O'Hare International
14h 37m
C$ 491
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 1 Nov
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Mon, 5 Nov
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 279
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
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

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

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.

Fri, 16 Nov
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sat, 24 Nov
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 297
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Okay 5.6

Flight was delayed.

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 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!!!!

Tue, 16 Oct
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Thu, 18 Oct
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
C$ 303
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
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 5.6

Flight was delayed.

MDW
YTZ
Excellent 8.0

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

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

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Excellent 8.0

Delay

Fri, 9 Nov
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Mon, 12 Nov
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 303
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
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
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

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

Sat, 1 Dec
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Tue, 4 Dec
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 303
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

MDW
YTZ
Excellent 10.0

Service of crew and snacks

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
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

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, 26 Oct
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Sun, 28 Oct
YTZ
Toronto Island
MDW
Chicago Midway
1h 45m
C$ 309
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
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 9.6

it was such a smooth flight

all good

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

Comfy large seats. Great service

Little slow to leave

Tue, 16 Oct
ORD
Chicago O'Hare International
YTZ
Toronto Island
17h 34m
Thu, 18 Oct
YTZ
Toronto Island
ORD
Chicago O'Hare International
6h 34m
C$ 528
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Mon, 5 Nov
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Mon, 12 Nov
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 310
Trip: 8 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

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

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

MDW
YTZ
Excellent 10.0

Service of crew and snacks

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 8.0

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!

Thu, 3 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sat, 5 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 327
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
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

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Excellent 9.6

it was such a smooth flight

all good

MDW
YTZ
Excellent 8.0

Delay

MDW
YTZ
Excellent 8.0

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

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

Sat, 9 Feb
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sat, 16 Feb
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
C$ 356
Trip: 8 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

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

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

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

Service of crew and snacks

MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

MDW
YTZ
Good 7.0

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.

Fri, 5 Oct
ORD
Chicago O'Hare International
YTZ
Toronto Island
25h 20m
Sun, 7 Oct
YTZ
Toronto Island
ORD
Chicago O'Hare International
19h 23m
C$ 755
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 29 Sep
ORD
Chicago O'Hare International
YTZ
Toronto Island
20h 08m
Mon, 1 Oct
YTZ
Toronto Island
ORD
Chicago O'Hare International
13h 49m
C$ 871
Trip: 3 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 29 Sep
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Sun, 30 Sep
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
C$ 573
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
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

Comfy large seats. Great service

Little slow to leave

MDW
YTZ
Good 7.0

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.

MDW
YTZ
Excellent 10.0

Nice flight

Highly recommend it

MDW
YTZ
Okay 5.6

Flight was delayed.

Fri, 28 Sep
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Sun, 30 Sep
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
C$ 630
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 97 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

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

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

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

Service of crew and snacks

MDW
YTZ
Good 7.0

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.

MDW
YTZ
Excellent 9.6

Comfy large seats. Great service

Little slow to leave

Show more results
*
Prices are per person, are for e–tickets and include all taxes & fees in CAD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

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,
please send us an and someone from our team will get back to you promptly.

^
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.

Forgot password?

Enter the email associated with your account in the field below and we'll email you a link to reset your password.

Cancel