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Toronto Island to Illinois Flight Information

Flights Arrive in Illinois
Flights Depart from Toronto Island
Flight Price C$ 241
Airlines Porter Airlines, Air Canada

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

Airports
Origin
Toronto
C$ 241
only
C$ 241
Destination
Chicago
C$ 359
only
C$ 359
C$ 241
only
C$ 241
Thu, 6 Dec
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, 9 Dec
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

Thu, 20 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
5h 07m
Mon, 31 Dec
ORD
Chicago O'Hare International
YTZ
Toronto Island
4h 35m
C$ 359
Trip: 12 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 23,220 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
RDU
Mediocre 3.3

Pros: Nothing

Cons: I didn’t like anything about this flight, except that we arrived safely. I had the last seat, next to the toilet, and that container or whatever it is, was dirty. Every time someone flushed, I was bathed in the smell of urine. It was raining in Toronto; consequently, my checked bag was wet through. I’m glad I was coming home rather than arriving at a vacation destination, where all my stuff would’ve been wet. I’d like to see some effort put into keeping my bag dry. Also, the passengers had to slog through the rain to get on the plane!

YYZ
UVF
Excellent 8.8

Pros: on time departure, early arrival

YXE
YYZ
Good 6.3

Pros: Quick boarding and takeoff

Cons: The sound connections for the in flight entertainment was faulty. Bring your own device would be better. Seats were uncomfortable, they need replacing.

LAX
YVR
Good 7.0

Pros: The stewardess with the amazing figure! I didn’t use the entertainment or order food so I can’t comment on those.

LAX
YVR
Okay 4.3

Cons: Compared to other airlines Air Canada is just so bad. Crew are always slow. The flight never boards on time or leaves on time. I don’t think I’ve ever been on an Air Canada flight that leaves on time. It’s incredibly frustrating. The staff were rude and cold on this flight and very very slow. I usually don’t write reviews like this but honestly can’t find anything good to say about this last flight. It was just bad.

Wed, 5 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
8h 18m
Thu, 24 Jan
ORD
Chicago O'Hare International
YTZ
Toronto Island
12h 13m
C$ 435
Trip: 51 days
Overall 0.0 Poor
Based on 0 reviews
Mon, 10 Dec
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Thu, 13 Dec
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

Mon, 7 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Tue, 15 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 10.0

Cons: Good

Tue, 8 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Wed, 16 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

Wed, 9 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Thu, 17 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 10.0

Cons: Good

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

Thu, 10 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Fri, 18 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Good 6.4

Cons: Major delays that were poorly handled.

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

Mon, 24 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
5h 07m
Mon, 31 Dec
ORD
Chicago O'Hare International
YTZ
Toronto Island
4h 35m
C$ 359
Trip: 8 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 23,220 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YVR
YEG
Excellent 10.0

Pros: They have the best blankets! I always get cold but the blankets are nice and thick. The entertainment system was easy to use with a wide variety to choose from. The seats are comfortable and easy to sleep in. Overall just a great comfortable trip!

YYZ
UVF
Excellent 8.8

Pros: on time departure, early arrival

LAX
YVR
Okay 4.3

Cons: Compared to other airlines Air Canada is just so bad. Crew are always slow. The flight never boards on time or leaves on time. I don’t think I’ve ever been on an Air Canada flight that leaves on time. It’s incredibly frustrating. The staff were rude and cold on this flight and very very slow. I usually don’t write reviews like this but honestly can’t find anything good to say about this last flight. It was just bad.

YYZ
RDU
Mediocre 3.3

Pros: Nothing

Cons: I didn’t like anything about this flight, except that we arrived safely. I had the last seat, next to the toilet, and that container or whatever it is, was dirty. Every time someone flushed, I was bathed in the smell of urine. It was raining in Toronto; consequently, my checked bag was wet through. I’m glad I was coming home rather than arriving at a vacation destination, where all my stuff would’ve been wet. I’d like to see some effort put into keeping my bag dry. Also, the passengers had to slog through the rain to get on the plane!

YOW
YYC
Okay 4.6

Cons: No snacks unless you are willing to pay more than 10 dollars lol

Fri, 11 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sat, 19 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

Thu, 27 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
5h 07m
Mon, 31 Dec
ORD
Chicago O'Hare International
YTZ
Toronto Island
4h 35m
C$ 359
Trip: 5 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 23,220 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
RDU
Mediocre 3.3

Pros: Nothing

Cons: I didn’t like anything about this flight, except that we arrived safely. I had the last seat, next to the toilet, and that container or whatever it is, was dirty. Every time someone flushed, I was bathed in the smell of urine. It was raining in Toronto; consequently, my checked bag was wet through. I’m glad I was coming home rather than arriving at a vacation destination, where all my stuff would’ve been wet. I’d like to see some effort put into keeping my bag dry. Also, the passengers had to slog through the rain to get on the plane!

YVR
YEG
Excellent 10.0

Pros: They have the best blankets! I always get cold but the blankets are nice and thick. The entertainment system was easy to use with a wide variety to choose from. The seats are comfortable and easy to sleep in. Overall just a great comfortable trip!

YVR
SFO
Mediocre 2.0

Pros: Absolutely nothing horrible flight

Cons: We were delayed 1hour and 45 minutes leaving Vancouver. As a result we missed our flight to Tokyo. We were promised by the flight attendant that our flights would be rebooked upon arrival in SAN Francisco and they were not.

YYZ
UVF
Excellent 8.8

Pros: on time departure, early arrival

LAX
YVR
Okay 4.3

Cons: Compared to other airlines Air Canada is just so bad. Crew are always slow. The flight never boards on time or leaves on time. I don’t think I’ve ever been on an Air Canada flight that leaves on time. It’s incredibly frustrating. The staff were rude and cold on this flight and very very slow. I usually don’t write reviews like this but honestly can’t find anything good to say about this last flight. It was just bad.

Sat, 12 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, 20 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

Fri, 28 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
5h 07m
Mon, 31 Dec
ORD
Chicago O'Hare International
YTZ
Toronto Island
4h 35m
C$ 359
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 23,220 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YXE
YYZ
Good 6.3

Pros: Quick boarding and takeoff

Cons: The sound connections for the in flight entertainment was faulty. Bring your own device would be better. Seats were uncomfortable, they need replacing.

BOS
YYZ
Good 7.6

Pros: Nice seats fast boarding

Cons: Snack can be more richer

YVR
LHR
Good 7.6

Pros: I’m not sure whether Air Canada has turned over a new leaf or Boeing built a better airplane. Maybe a bit of both. The ambiance is marvellous in the 787. The Flight attendants were attentive and thoughtful (remembering what I was drinking). We left snd landed on time. And the entertainment system is one of the best I’ve experienced.

Cons: I couldn’t properly adjust my seat. That shouldn’t happen on such a new aircraft. Other than that, and the fact I couldn’t sleep, everything was good.

YOW
YYC
Okay 4.6

Cons: No snacks unless you are willing to pay more than 10 dollars lol

LHR
YYZ
Excellent 8.3

Pros: comfort, entertainment, food

Cons: there were two really rude flight attendants....almost like they didn;t want to serve you. One of the ladies even literally threw a drink onto my tray. thank god it was sealed. Air canada needs to do a better job of dealing with this type of behaviour. It happens far too often with their staff

Wed, 5 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
6h 32m
Thu, 6 Dec
ORD
Chicago O'Hare International
YTZ
Toronto Island
6h 56m
C$ 437
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Sun, 13 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Mon, 21 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Okay 4.0

Cons: Got to Billy Bishop, only to find out flight is delayed 2 hours.

YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Excellent 8.0

Cons: Delay

Wed, 26 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
4h 57m
Mon, 31 Dec
ORD
Chicago O'Hare International
YTZ
Toronto Island
4h 35m
C$ 360
Trip: 6 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 23,220 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
BOS
YYZ
Good 7.6

Pros: Nice seats fast boarding

Cons: Snack can be more richer

LAX
YVR
Good 7.0

Pros: The stewardess with the amazing figure! I didn’t use the entertainment or order food so I can’t comment on those.

YYZ
UVF
Excellent 8.8

Pros: on time departure, early arrival

LHR
YYZ
Excellent 8.3

Pros: comfort, entertainment, food

Cons: there were two really rude flight attendants....almost like they didn;t want to serve you. One of the ladies even literally threw a drink onto my tray. thank god it was sealed. Air canada needs to do a better job of dealing with this type of behaviour. It happens far too often with their staff

YVR
YEG
Excellent 10.0

Pros: They have the best blankets! I always get cold but the blankets are nice and thick. The entertainment system was easy to use with a wide variety to choose from. The seats are comfortable and easy to sleep in. Overall just a great comfortable trip!

Tue, 11 Dec
YTZ
Toronto Island
ORD
Chicago O'Hare International
8h 18m
Wed, 12 Dec
ORD
Chicago O'Hare International
YTZ
Toronto Island
9h 14m
C$ 457
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Mon, 14 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Tue, 22 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Excellent 9.6

Pros: Convenient, easy boarding, snacks and free wine on leg from toronto to chicago

YTZ
MDW
Excellent 8.0

Cons: Delay

YTZ
MDW
Excellent 10.0

Pros: It was hassle free. Trace and arrival times were perfect. Thank you for caring.

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

YTZ
MDW
Excellent 8.0

Pros: I liked the lounge

Cons: There were a lot of people and not enough outlets

Thu, 3 Jan
YTZ
Toronto Island
ORD
Chicago O'Hare International
4h 57m
Sun, 6 Jan
ORD
Chicago O'Hare International
YTZ
Toronto Island
4h 40m
C$ 360
Trip: 4 days
7.1GoodShow reviews
Overall 7.1 Good
Based on 23,220 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.9
Food
6.5
YYZ
SFO
Mediocre 3.0

Cons: Plane way too cramped. Made me check my bag but it clearly would have fit and there was lots of room overhead. Still waiting for my bag more than half hour after my flight. Very unhappy. Totally unacceptable.

YVR
LHR
Good 7.6

Pros: I’m not sure whether Air Canada has turned over a new leaf or Boeing built a better airplane. Maybe a bit of both. The ambiance is marvellous in the 787. The Flight attendants were attentive and thoughtful (remembering what I was drinking). We left snd landed on time. And the entertainment system is one of the best I’ve experienced.

Cons: I couldn’t properly adjust my seat. That shouldn’t happen on such a new aircraft. Other than that, and the fact I couldn’t sleep, everything was good.

LAX
YVR
Good 7.0

Pros: The stewardess with the amazing figure! I didn’t use the entertainment or order food so I can’t comment on those.

BOS
YYZ
Good 7.6

Pros: Nice seats fast boarding

Cons: Snack can be more richer

YYZ
UVF
Excellent 8.8

Pros: on time departure, early arrival

Tue, 15 Jan
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Wed, 23 Jan
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
C$ 241
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 126 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
YTZ
MDW
Mediocre 3.6

Pros: Once we got on the flight it was fine.

Cons: Worst issues was official announcement that flight was cancelled and then no announcement that it was actually not cancelled. Many people went home or were standing in line waiting to rebook when the flight left. We just barely made it on because we overheard staff talking to another couple!! Not acceptable. They should have made announcements over the speakers and should have called passengers by name to come to check in. Porter had flooding problems that meant many people crowding into small space and it prevented passengers from food or drinks. They eventually handed out water. They should have provided vouchers or brought in other food and beverages.

YTZ
MDW
Excellent 9.3

Pros: Fast and convenient

YTZ
MDW
Mediocre 2.0

Pros: Free bar nuts while delayed 10 hours

Cons: Kicked us out of the airport when connection cancelled, NEVER fly Porter!!!! The horror stories are true as could be

YTZ
MDW
Excellent 8.3

Pros: fast

Cons: no TSA precheck

YTZ
MDW
Excellent 10.0

Pros: First time in 10 flights in 3 months flying with Porter in time - what a miracle!

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