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

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Chicago Midway to Toronto Island Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Toronto Island
Flights Depart from Chicago Midway
Flight Price $195
Distance 443 miles
Airlines Porter Airlines

Good to Know

Good Deal:
$245
or less round-trip within
2 months
of travel is a good deal

When to Book Flights from Chicago Midway to Toronto Island

Estimated round-trip price
Flight prices as travel date approaches
-1 day
-2 days

Top Tips for Finding a Cheap Flight

The cheapest flight from Chicago Midway to Toronto Island was found 32 days before departure, on average.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 2% more expensive 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 Midway to Toronto Island Flights

How long does a flight from Chicago Midway to Toronto Island take?
An average nonstop flight takes 1h 35m, covering a distance of 443 miles.
How many flights are there between Chicago Midway and Toronto Island?
There are 58 (nonstop) flights between Chicago Midway and Toronto Island per week, averaging 8 per day.
Which airlines provide the cheapest flights from Chicago Midway to Toronto Island?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines ($195)
Do I need a passport to fly between Chicago Midway and Toronto Island?
Yes.
Which airlines fly most frequently between Chicago Midway and Toronto Island?
Porter Airlines (8 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Toronto Island?
For Chicago Midway to Toronto Island, Wednesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Toronto Island back to Chicago Midway, the best deals are generally found on Thursday, with Monday being the most expensive.

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

Airports
Origin
Chicago
$195
only
$195
Destination
Toronto
$195
only
$195
Wed, Dec 5
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
Tue, Dec 11
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

MDW
YTZ
Excellent 10.0

Pros: 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 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 8.0

Pros: Snacks and pleasant mannerism of the stewardess

MDW
YTZ
Excellent 8.0

Pros: 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

Cons: 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, Dec 7
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Tue, Dec 11
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Okay 5.6

Cons: Flight was delayed.

MDW
YTZ
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

MDW
YTZ
Excellent 8.0

Pros: 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

Cons: 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, Dec 8
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sat, Jan 26
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 50 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 10.0

Pros: Nice flight

Cons: Highly recommend it

MDW
YTZ
Okay 5.6

Cons: Flight was delayed.

MDW
YTZ
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 8.0

Pros: Snacks and pleasant mannerism of the stewardess

Fri, Jan 18
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Tue, Jan 22
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Excellent 10.0

Pros: 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 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 10.0

Pros: Nice flight

Cons: Highly recommend it

MDW
YTZ
Excellent 9.6

Pros: Comfy large seats. Great service

Cons: Little slow to leave

Mon, Feb 11
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Wed, Feb 13
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Excellent 9.6

Pros: Comfy large seats. Great service

Cons: Little slow to leave

MDW
YTZ
Excellent 8.0

Pros: 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

Cons: 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
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

Mon, Apr 1
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sat, Apr 6
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 6 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Good 7.0

Cons: 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 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

Fri, Dec 14
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sun, Dec 16
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Excellent 10.0

Pros: 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

Pros: Comfy large seats. Great service

Cons: Little slow to leave

MDW
YTZ
Excellent 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 8.0

Pros: Snacks and pleasant mannerism of the stewardess

Sat, Apr 6
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Fri, Apr 12
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 10.0

Pros: Nice flight

Cons: Highly recommend it

MDW
YTZ
Excellent 8.0

Pros: 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

Cons: 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
Good 7.0

Cons: 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 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 10.0

Pros: 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.

Sat, Apr 13
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Mon, Apr 15
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 10.0

Pros: 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 7.0

Cons: 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

Pros: Service of crew and snacks

MDW
YTZ
Excellent 9.6

Pros: Comfy large seats. Great service

Cons: Little slow to leave

MDW
YTZ
Excellent 10.0

Pros: Nice flight

Cons: Highly recommend it

Mon, Mar 11
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Fri, Mar 15
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Good 7.0

Cons: 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

Pros: Comfy large seats. Great service

Cons: Little slow to leave

MDW
YTZ
Excellent 8.0

Pros: Snacks and pleasant mannerism of the stewardess

Thu, Dec 6
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sun, Dec 9
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Good 7.0

Cons: 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

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Excellent 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

Sat, Dec 8
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Wed, Dec 12
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 8.0

Pros: 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

Cons: 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

Pros: Nice flight

Cons: Highly recommend it

MDW
YTZ
Excellent 10.0

Pros: 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.

Thu, Dec 27
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sun, Jan 6
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 11 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 8.0

Pros: 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

Cons: 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

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Okay 5.6

Cons: Flight was delayed.

MDW
YTZ
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

Fri, Dec 28
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Thu, Jan 3
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Good 7.0

Cons: 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

Pros: Nice flight

Cons: Highly recommend it

MDW
YTZ
Excellent 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

MDW
YTZ
Excellent 9.6

Pros: Comfy large seats. Great service

Cons: Little slow to leave

MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

Sat, Dec 29
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Fri, Jan 4
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 8.0

Pros: Snacks and pleasant mannerism of the stewardess

MDW
YTZ
Excellent 10.0

Pros: Service of crew and snacks

MDW
YTZ
Excellent 10.0

Pros: Nice flight

Cons: Highly recommend it

MDW
YTZ
Excellent 9.3

Pros: It was quick and easy to board the plane with no dlays

Cons: A little bumpy

Wed, Jan 9
MDW
Chicago Midway
YTZ
Toronto Island
1h 35m
Mon, Jan 14
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 6 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 10.0

Pros: 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 8.0

Pros: Snacks and pleasant mannerism of the stewardess

MDW
YTZ
Good 7.0

Cons: 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

Pros: Service of crew and snacks

MDW
YTZ
Excellent 9.6

Pros: Comfy large seats. Great service

Cons: Little slow to leave

Thu, Jan 24
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Sun, Jan 27
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 9.6

Pros: Comfy large seats. Great service

Cons: Little slow to leave

MDW
YTZ
Excellent 10.0

Pros: Service of crew and snacks

MDW
YTZ
Excellent 10.0

Pros: Nice flight

Cons: Highly recommend it

Wed, Feb 6
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Wed, Feb 20
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 15 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Good 7.0

Cons: 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

Pros: Nice flight

Cons: Highly recommend it

MDW
YTZ
Excellent 9.6

Pros: it was such a smooth flight

Cons: all good

MDW
YTZ
Excellent 10.0

Pros: Service of crew and snacks

MDW
YTZ
Excellent 8.0

Cons: Delay

Sat, Mar 23
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Mon, Apr 1
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 10 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

Cons: Delay

MDW
YTZ
Excellent 9.6

Pros: Comfy large seats. Great service

Cons: Little slow to leave

MDW
YTZ
Good 7.0

Cons: 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

Pros: 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

Pros: Nice flight

Cons: Highly recommend it

Tue, Apr 2
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Wed, Apr 10
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Trip: 9 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 101 reviews
Boarding
7.9
Comfort
8.0
Crew
8.4
Entertainment
6.9
Food
7.8
MDW
YTZ
Excellent 8.0

Pros: Snacks and pleasant mannerism of the stewardess

MDW
YTZ
Excellent 8.0

Pros: 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

Cons: 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
Good 7.3

Pros: Crew were very professionally and very attentive to my needs as a mom traveling with an infant.

MDW
YTZ
Good 7.0

Cons: 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

Pros: Nice flight

Cons: Highly recommend it

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