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

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

Sat 2/24
Sat 3/3
Any month
Compare vs. KAYAK |

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $225 or less.

FAQs for Booking Toronto Island to Chicago Flights

How long does a flight from Toronto Island to Chicago take?
An average nonstop flight takes 1h 45m, covering a distance of 434 miles.
How many flights are there between Toronto Island and Chicago?
There are 34 (nonstop) flights between Toronto Island and Chicago per week, averaging 5 per day.
Which airlines provide the cheapest flights from Toronto Island to Chicago?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines ($216), Air Canada ($322) and Multiple Airlines ($416).
Do I need a passport to fly between Toronto Island and Chicago?
Yes.
Which airlines fly most frequently between Toronto Island and Chicago?
Porter Airlines (4 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Toronto Island to Chicago?
For Toronto Island to Chicago, Tuesday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago back to Toronto Island, the best deals are generally found on Monday, with Friday being the most expensive.

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

Airports
Origin
Toronto
$216
only
$216
Destination
Chicago
$322
only
$322
$216
only
$216
Tue, Apr 17
YTZ
MDW
1h 45m
Thu, Apr 26
MDW
YTZ
1h 40m
Trip: 10 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Good 6.6

Onboard crew was very nice

Crew didn't answer any of my questions, were snappy, and rude.

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

Sat, Mar 10
YTZ
ORD
5h 10m
Sat, Mar 17
ORD
YTZ
5h 05m
Trip: 7 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 21542 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
SAN
YVR
Good 6.0

Overhead bins were tiny.

LGA
YYZ
Okay 5.0

Stewardess seems very annoyed with flight. There was turbulence so the passengers needed to stay seated - a gentleman next to me asked for a glass of water since there was no refreshment service - the stewardess was very short with him. It’s not the passengers fault. I was surprised - usually the staff is a lot more professional than that.

LAX
YYC
Good 6.0

poor entertainment choices. Reading lights didn't work. I traveled with my wife, we were unable to read because reading lights didn't work.

YUL
YVR
Okay 4.3

Generous leg room in coach class

Sat on the runway for almost an hour both to and from my destination

TLV
YYZ
Mediocre 2.0

Connecting flight in Toronto late 4 HOURS!!!!! There is no excuse for such delay. Another plane should have been made available for the flight.

Sat, Apr 28
YTZ
ORD
8h 13m
Tue, May 1
ORD
YTZ
7h 02m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Fri, Mar 23
YTZ
MDW
1h 50m
Mon, Mar 26
MDW
YTZ
1h 37m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

Delay

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Good 6.6

Onboard crew was very nice

Crew didn't answer any of my questions, were snappy, and rude.

YTZ
MDW
Good 7.3

Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight.

Louder than a usual commercial flight, probably due to being a turboprop aircraft.

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

Fri, May 4
YTZ
MDW
1h 45m
Tue, May 8
MDW
YTZ
1h 40m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Delay

Fri, Jun 1
YTZ
MDW
1h 45m
Thu, Jun 7
MDW
YTZ
1h 40m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 7.3

Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight.

Louder than a usual commercial flight, probably due to being a turboprop aircraft.

YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

Tue, Jun 5
YTZ
MDW
1h 45m
Fri, Jun 8
MDW
YTZ
1h 40m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

Fri, Mar 23
YTZ
MDW
1h 50m
Sun, Mar 25
MDW
YTZ
1h 37m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 8.0

Delay

Sat, Mar 17
YTZ
MDW
1h 50m
Sun, Mar 18
MDW
YTZ
1h 37m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Good 6.6

Onboard crew was very nice

Crew didn't answer any of my questions, were snappy, and rude.

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Fri, Apr 6
YTZ
MDW
1h 50m
Sun, Apr 8
MDW
YTZ
1h 37m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Good 7.3

Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight.

Louder than a usual commercial flight, probably due to being a turboprop aircraft.

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Good 6.0

Efficient

Late flight

Fri, Jun 29
YTZ
ORD
7h 37m
Tue, Jul 3
ORD
YTZ
6h 50m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Thu, Apr 5
YTZ
MDW
1h 50m
Sun, Apr 8
MDW
YTZ
1h 37m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Good 6.6

Onboard crew was very nice

Crew didn't answer any of my questions, were snappy, and rude.

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

Fri, Aug 24
YTZ
ORD
6h 29m
Mon, Aug 27
ORD
YTZ
5h 55m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sun, Jul 1
YTZ
MDW
1h 45m
Sat, Jul 14
MDW
YTZ
1h 40m
Trip: 14 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 7.3

Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight.

Louder than a usual commercial flight, probably due to being a turboprop aircraft.

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

Sat, Feb 24
YTZ
ORD
4h 45m
Sat, Mar 3
ORD
YTZ
5h 35m
Trip: 8 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 21542 reviews
Overall
7.2
Boarding
7.3
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YUL
YVR
Okay 4.3

Generous leg room in coach class

Sat on the runway for almost an hour both to and from my destination

LGA
YYZ
Mediocre 2.6

Sitting on the tarmac for an hour before takeoff Cramped seats No beverage service (supposedly, because of turbulence, although other airlines have not let turbulence stop them from serving food and drink)

LIR
YYZ
Okay 5.3

Uncomfortable

LAX
YYZ
Excellent 8.0

Plane delayed 1 hour and a half. No compensation.

LAX
YYC
Good 6.0

poor entertainment choices. Reading lights didn't work. I traveled with my wife, we were unable to read because reading lights didn't work.

Fri, May 4
YTZ
ORD
12h 10m
Tue, May 8
ORD
YTZ
10h 38m
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Aug 11
YTZ
MDW
1h 45m
Fri, Aug 24
MDW
YTZ
1h 40m
Trip: 14 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 7.3

Quick and convenient boarding, terrific airport, generous terminal lounge for relaxing pre-flight.

Louder than a usual commercial flight, probably due to being a turboprop aircraft.

YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

YTZ
MDW
Excellent 9.2

There were mechanical delays, so Porter gave an $8 voucher to spend in the airport, which was a nice touch since I had never received that from other airlines who also had mechanical delays.

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Good 6.0

Efficient

Late flight

Fri, Jun 29
YTZ
ORD
7h 37m
Mon, Jul 2
ORD
YTZ
11h 39m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Tue, Jul 17
YTZ
ORD
6h 29m
Fri, Jul 20
ORD
YTZ
6h 15m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, Aug 18
YTZ
MDW
1h 45m
Mon, Aug 27
MDW
YTZ
1h 40m
Trip: 10 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 100 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Okay 5.3

If Porter was a budget airline the dreadful customer service might be partially understood, but it's not. Somebody needs to put passenger considerations into operational planning for situations where travel plans are disrupted, especially when they are because of mechanical or airline problems.

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 8.0

Delay

Toronto Island to Chicago Flight Information

Avg. Flight Duration 1h 42m
Flights Arrive in Chicago
Flights Depart from Toronto Island
Flight Price $216
Distance 434 miles
Airlines Porter Airlines, Air Canada
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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.