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

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Good to Know

Average price:
C$ 340
(avg. price over the last 2 weeks)
Good Deal:
C$ 296
or less (round trip)

When to Book Flights from Toronto Island to Chicago Midway

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for C$ 296 or less.
The cheapest flight from Toronto Island to Chicago Midway was found, on average, 86 days before departure.
Book at least 3 weeks before departure in order to get a below-average price.
Morning departure is around 3% cheaper 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 713 km.
How many flights are there between Toronto Island and Chicago Midway?
There are 34 (nonstop) flights between Toronto Island and Chicago Midway per week, averaging 5 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 (C$ 274)
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 (4 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 Midway?
For Toronto Island to Chicago Midway, Tuesday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago Midway back to Toronto Island, the best deals are generally found on Monday, with Thursday being the most expensive.

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

Airports
Origin
Toronto
C$ 274
only
C$ 274
Destination
Chicago
C$ 274
only
C$ 274
Tue, 17 Apr
YTZ
MDW
1h 45m
Thu, 26 Apr
MDW
YTZ
1h 40m
C$ 274
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 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 6.4

Major delays that were poorly handled.

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

Fri, 6 Apr
YTZ
MDW
1h 50m
Sun, 15 Apr
MDW
YTZ
1h 40m
C$ 279
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

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Excellent 8.0

Delay

YTZ
MDW
Good 6.0

Efficient

Late flight

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.

Fri, 23 Mar
YTZ
MDW
1h 50m
Mon, 26 Mar
MDW
YTZ
1h 37m
C$ 281
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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Good

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

Tue, 10 Apr
YTZ
MDW
1h 50m
Wed, 18 Apr
MDW
YTZ
1h 40m
C$ 281
Trip: 9 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
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
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

Fri, 4 May
YTZ
MDW
1h 45m
Tue, 8 May
MDW
YTZ
1h 40m
C$ 281
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
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
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 8.0

I liked the lounge

There were a lot of people and not enough outlets

Tue, 8 May
YTZ
MDW
1h 45m
Sun, 13 May
MDW
YTZ
1h 40m
C$ 281
Trip: 6 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

I liked the lounge

There were a lot of people and not enough outlets

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

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
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.

Fri, 1 Jun
YTZ
MDW
1h 45m
Thu, 7 Jun
MDW
YTZ
1h 40m
C$ 281
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 8.0

Delay

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

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.

Fri, 15 Jun
YTZ
MDW
1h 45m
Wed, 20 Jun
MDW
YTZ
1h 40m
C$ 281
Trip: 6 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
Good 6.0

Efficient

Late flight

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
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, 22 Mar
YTZ
MDW
1h 50m
Mon, 26 Mar
MDW
YTZ
1h 37m
C$ 282
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 6.4

Major delays that were poorly handled.

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 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.

Fri, 23 Mar
YTZ
MDW
1h 50m
Sun, 25 Mar
MDW
YTZ
1h 37m
C$ 282
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 8.0

Delay

YTZ
MDW
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.0

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Mon, 9 Apr
YTZ
MDW
1h 50m
Thu, 19 Apr
MDW
YTZ
1h 40m
C$ 282
Trip: 11 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

Polite crew

Would like a sandwich instead of nuts

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
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, 22 Apr
YTZ
MDW
1h 45m
Thu, 26 Apr
MDW
YTZ
1h 40m
C$ 282
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
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
Good 6.4

Major delays that were poorly handled.

YTZ
MDW
Mediocre 2.0

Nothing

Everything

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.

Tue, 3 Apr
YTZ
MDW
1h 50m
Fri, 6 Apr
MDW
YTZ
1h 37m
C$ 283
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
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

Delay

YTZ
MDW
Good 6.0

Efficient

Late flight

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.

Fri, 4 May
YTZ
MDW
1h 45m
Mon, 7 May
MDW
YTZ
1h 40m
C$ 284
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
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 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 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.

Tue, 5 Jun
YTZ
MDW
1h 45m
Fri, 8 Jun
MDW
YTZ
1h 40m
C$ 284
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 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 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 10.0

Good

YTZ
MDW
Excellent 8.0

Delay

Thu, 5 Apr
YTZ
MDW
1h 50m
Sun, 8 Apr
MDW
YTZ
1h 37m
C$ 286
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
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 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 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, 20 Apr
YTZ
MDW
1h 45m
Sun, 22 Apr
MDW
YTZ
1h 40m
C$ 286
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 8.0

Polite crew

Would like a sandwich instead of nuts

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
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.

Sat, 12 May
YTZ
MDW
1h 45m
Tue, 15 May
MDW
YTZ
1h 40m
C$ 286
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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

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.

YTZ
MDW
Excellent 8.0

Delay

Tue, 5 Jun
YTZ
MDW
1h 45m
Sat, 9 Jun
MDW
YTZ
1h 40m
C$ 286
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
Excellent 8.3

fast

no TSA precheck

YTZ
MDW
Good 6.4

Major delays that were poorly handled.

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
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.

Fri, 16 Mar
YTZ
MDW
1h 50m
Mon, 9 Apr
MDW
YTZ
1h 37m
C$ 287
Trip: 25 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
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 8.3

fast

no TSA precheck

Show more results

Toronto Island to Chicago Midway Flight Information

Avg. Flight Duration 1h 43m
Flights Arrive in Chicago Midway
Flights Depart from Toronto Island
Flight Price C$ 274
Distance 713 km
Airlines Porter Airlines
*
Prices are per person, are for e–tickets and include all taxes & fees in CAD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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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.

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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.

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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.