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

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Toronto Island to Chicago Midway Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Chicago Midway
Flights Depart from Toronto Island
Flight Price $193
Distance 443 miles
Airlines Porter Airlines

Good to Know

When to Book Flights from Toronto Island to Chicago Midway

Top Tips for Finding a Cheap Flight

Book at least 1 week before departure in order to get a below-average price.
Morning departure is around 3% 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 Toronto Island to Chicago Midway Flights

How long does a flight from Toronto Island to Chicago Midway take?
An average nonstop flight takes 1h 45m, covering a distance of 443 miles.
How many flights are there between Toronto Island and Chicago Midway?
There are 76 (nonstop) flights between Toronto Island and Chicago Midway per week, averaging 10 per day.
Which airlines provide the cheapest flights from Toronto Island to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Porter Airlines ($193)
Do I need a passport to fly between Toronto Island and Chicago Midway?
Yes.
Which airlines fly most frequently between Toronto Island and Chicago Midway?
Porter Airlines (10 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Toronto Island to Chicago Midway?
For Toronto Island to Chicago Midway, Saturday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago Midway back to Toronto Island, the best deals are generally found on Wednesday, with Friday being the most expensive.

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

Airports
Origin
Toronto
$193
only
$193
Destination
Chicago
$193
only
$193
Sat, Nov 3
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Wed, Nov 7
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Mediocre 2.0

Nothing

Everything

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
Okay 4.0

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

YTZ
MDW
Good 6.6

Onboard crew was very nice

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

Sat, Oct 13
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Tue, Oct 16
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Okay 4.0

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

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

Sun, Oct 14
YTZ
Toronto Island
MDW
Chicago Midway
1h 45m
Tue, Oct 30
MDW
Chicago Midway
YTZ
Toronto Island
1h 40m
Trip: 17 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 9.6

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

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Fri, Oct 19
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Sun, Oct 21
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
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

YTZ
MDW
Mediocre 3.6

Once we got on the flight it was fine.

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
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Okay 4.0

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

Wed, Oct 24
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Tue, Oct 30
MDW
Chicago Midway
YTZ
Toronto Island
1h 40m
Trip: 7 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
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
Mediocre 3.6

Once we got on the flight it was fine.

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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 10.0

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

Thu, Oct 25
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Tue, Oct 30
MDW
Chicago Midway
YTZ
Toronto Island
1h 40m
Trip: 6 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 9.6

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

Fri, Oct 26
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Tue, Oct 30
MDW
Chicago Midway
YTZ
Toronto Island
1h 40m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
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

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Okay 4.0

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

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

Fri, Nov 30
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sat, Dec 1
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
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
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
Excellent 10.0

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

Fri, Dec 14
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Dec 16
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Mediocre 3.6

Once we got on the flight it was fine.

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

I liked the lounge

There were a lot of people and not enough outlets

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
Excellent 10.0

Good

Fri, Oct 12
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Mon, Oct 15
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Excellent 9.6

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

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Okay 4.0

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

YTZ
MDW
Excellent 8.0

Delay

Sat, Oct 13
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Sun, Oct 14
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Mediocre 3.6

Once we got on the flight it was fine.

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
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Excellent 9.6

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

YTZ
MDW
Okay 4.0

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

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Mon, Oct 8
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Tue, Oct 9
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 2 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Okay 4.0

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

YTZ
MDW
Excellent 8.0

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 8.0

Delay

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Wed, Oct 10
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Sat, Oct 13
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Good 6.4

Major delays that were poorly handled.

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
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Mediocre 2.0

Nothing

Everything

Thu, Oct 11
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Mon, Oct 15
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 5 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Excellent 8.3

fast

no TSA precheck

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
Mediocre 3.6

Once we got on the flight it was fine.

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
Mediocre 2.0

Nothing

Everything

Sat, Oct 13
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Mon, Oct 15
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
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
Mediocre 3.6

Once we got on the flight it was fine.

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

Good

YTZ
MDW
Excellent 10.0

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

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Mon, Oct 15
YTZ
Toronto Island
MDW
Chicago Midway
1h 47m
Thu, Oct 18
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Okay 4.0

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

YTZ
MDW
Mediocre 3.6

Once we got on the flight it was fine.

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

Delay

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

Thu, Oct 18
YTZ
Toronto Island
MDW
Chicago Midway
1h 45m
Sat, Oct 20
MDW
Chicago Midway
YTZ
Toronto Island
1h 42m
Trip: 3 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Mediocre 3.6

Once we got on the flight it was fine.

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
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Excellent 10.0

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

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Wed, Oct 31
YTZ
Toronto Island
MDW
Chicago Midway
1h 45m
Sat, Nov 3
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
Food
7.9
YTZ
MDW
Excellent 9.6

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

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Excellent 8.0

Delay

YTZ
MDW
Mediocre 3.6

Once we got on the flight it was fine.

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

I liked the lounge

There were a lot of people and not enough outlets

Thu, Nov 1
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Sun, Nov 4
MDW
Chicago Midway
YTZ
Toronto Island
1h 37m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Okay 4.0

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

Fri, Nov 2
YTZ
Toronto Island
MDW
Chicago Midway
1h 50m
Mon, Nov 5
MDW
Chicago Midway
YTZ
Toronto Island
1h 34m
Trip: 4 days
8.2ExcellentShow reviews
Overall 8.2 Excellent
Based on 119 reviews
Boarding
7.9
Comfort
7.9
Crew
8.4
Entertainment
6.9
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 10.0

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

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