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

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Fri 15/12
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Looking for a cheap flight? 25% of our users found flights on this route for C$ 313 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 40m, covering a distance of 698 km.
How many flights are there between Toronto Island and Chicago?
There are 79 (nonstop) flights between Toronto Island and Chicago per week, averaging 11 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 (C$ 233)
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 (11 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly from Toronto Island to Chicago?
For Toronto Island to Chicago, Saturday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Chicago back to Toronto Island, the best deals are generally found on Thursday, with Monday being the most expensive.

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

Airports
Origin
Toronto
C$ 233
only
C$ 233
Destination
Chicago
C$ 233
only
C$ 233
Sat, 6 Jan
YTZ
MDW
1h 50m
Fri, 12 Jan
MDW
YTZ
1h 37m
C$ 233
Trip: 7 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Good 6.0

Efficient

Late flight

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.

Thu, 4 Jan
YTZ
MDW
1h 50m
Mon, 8 Jan
MDW
YTZ
1h 37m
C$ 250
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Sat, 6 Jan
YTZ
MDW
1h 50m
Wed, 10 Jan
MDW
YTZ
1h 37m
C$ 250
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
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 8.3

fast

no TSA precheck

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Sun, 7 Jan
YTZ
MDW
1h 50m
Thu, 11 Jan
MDW
YTZ
1h 37m
C$ 250
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
Good 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

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

Tue, 9 Jan
YTZ
MDW
1h 50m
Fri, 12 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

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.

YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

Fri, 12 Jan
YTZ
MDW
1h 50m
Sun, 14 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
Excellent 10.0

Good

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

Sat, 13 Jan
YTZ
MDW
1h 50m
Wed, 17 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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 8.0

Breakfast, bars, etcnithin

Nada

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

Mon, 15 Jan
YTZ
MDW
1h 50m
Thu, 18 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

Tue, 16 Jan
YTZ
MDW
1h 50m
Wed, 17 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 2 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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 8.0

Breakfast, bars, etcnithin

Nada

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

Wed, 17 Jan
YTZ
MDW
1h 50m
Wed, 24 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 8 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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 6.0

Efficient

Late flight

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 8.0

I liked the lounge

There were a lot of people and not enough outlets

Thu, 18 Jan
YTZ
MDW
1h 40m
Wed, 24 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 7 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

Fri, 19 Jan
YTZ
MDW
1h 50m
Sun, 21 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
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 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Sun, 21 Jan
YTZ
MDW
1h 50m
Wed, 24 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

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.

Mon, 22 Jan
YTZ
MDW
1h 50m
Fri, 26 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

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

Polite crew

Would like a sandwich instead of nuts

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.

Wed, 24 Jan
YTZ
MDW
1h 50m
Thu, 25 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 2 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

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.

Thu, 25 Jan
YTZ
MDW
1h 40m
Wed, 31 Jan
MDW
YTZ
1h 37m
C$ 261
Trip: 7 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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 6.0

Efficient

Late flight

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
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

Wed, 31 Jan
YTZ
MDW
1h 50m
Fri, 2 Feb
MDW
YTZ
1h 37m
C$ 261
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 10.0

Good

Thu, 1 Feb
YTZ
MDW
1h 50m
Sun, 4 Feb
MDW
YTZ
1h 37m
C$ 261
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 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
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
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
Good 6.0

Efficient

Late flight

Sat, 3 Feb
YTZ
MDW
1h 50m
Sat, 10 Feb
MDW
YTZ
1h 37m
C$ 261
Trip: 8 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Good 6.6

Onboard crew was very nice

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

YTZ
MDW
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Mediocre 2.0

Nothing

Everything

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.

Sun, 4 Feb
YTZ
MDW
1h 50m
Thu, 22 Feb
MDW
YTZ
1h 37m
C$ 261
Trip: 19 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 97 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Porter Airlines is the best I've been on within North America. Delighted that my 2nd flight was still Porter.

YTZ
MDW
Excellent 10.0

Good

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.

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

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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.