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

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Wed 22/11
Wed 29/11
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Good to Know

Average price:
C$ 397
(avg. price over the last 2 weeks)
Good Deal:
C$ 300
or less (round trip)

When to Book Flights from Toronto Island to Chicago Midway

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

When looking for a cheap flight, consider that 25% of our users selected a flight on this route for C$ 299 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 2% 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 40m, covering a distance of 713 km.
How many flights are there between Toronto Island and Chicago Midway?
There are 66 (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 (C$ 240)
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 (9 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, Monday 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 Tuesday, with Friday being the most expensive.

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

Airports
Origin
Toronto
C$ 240
only
C$ 240
Destination
Chicago
C$ 240
only
C$ 240
Mon, 11 Dec
YTZ
MDW
1h 50m
Wed, 13 Dec
MDW
YTZ
1h 37m
C$ 240
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Tue, 12 Dec
YTZ
MDW
1h 50m
Thu, 14 Dec
MDW
YTZ
1h 35m
C$ 240
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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 6.6

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 8.0

I liked the lounge

There were a lot of people and not enough outlets

Fri, 12 Jan
YTZ
MDW
1h 50m
Sun, 14 Jan
MDW
YTZ
1h 37m
C$ 240
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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 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

Thu, 15 Feb
YTZ
MDW
1h 50m
Mon, 19 Feb
MDW
YTZ
1h 37m
C$ 240
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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
Excellent 8.0

Breakfast, bars, etcnithin

Nada

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 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

Sat, 17 Feb
YTZ
MDW
1h 50m
Mon, 19 Feb
MDW
YTZ
1h 37m
C$ 258
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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

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

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, 12 Jan
YTZ
MDW
1h 40m
Mon, 15 Jan
MDW
YTZ
1h 37m
C$ 263
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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 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
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, 9 Mar
YTZ
MDW
1h 50m
Tue, 13 Mar
MDW
YTZ
1h 37m
C$ 263
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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
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
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.

Fri, 22 Dec
YTZ
MDW
1h 50m
Thu, 28 Dec
MDW
YTZ
1h 37m
C$ 279
Trip: 7 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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

Polite crew

Would like a sandwich instead of nuts

YTZ
MDW
Excellent 10.0

Good

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Thu, 22 Feb
YTZ
MDW
1h 50m
Mon, 26 Feb
MDW
YTZ
1h 37m
C$ 279
Trip: 5 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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
Excellent 10.0

Good

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
Good 6.6

Onboard crew was very nice

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

Fri, 25 May
YTZ
MDW
1h 45m
Sun, 27 May
MDW
YTZ
1h 40m
C$ 285
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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
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
Mediocre 2.0

Nothing

Everything

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, 25 May
YTZ
MDW
1h 45m
Mon, 28 May
MDW
YTZ
1h 40m
C$ 288
Trip: 4 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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
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 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

Fri, 9 Mar
YTZ
MDW
1h 50m
Sun, 11 Mar
MDW
YTZ
1h 37m
C$ 315
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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

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
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.

Sat, 2 Dec
YTZ
MDW
1h 50m
Thu, 21 Dec
MDW
YTZ
1h 37m
C$ 385
Trip: 20 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
YTZ
MDW
Excellent 10.0

Good

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
Mediocre 2.0

Nothing

Everything

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Wed, 22 Nov
YTZ
MDW
1h 50m
Tue, 19 Dec
MDW
YTZ
1h 37m
C$ 396
Trip: 28 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 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 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.

Fri, 24 Nov
YTZ
MDW
1h 50m
Sun, 26 Nov
MDW
YTZ
1h 37m
C$ 524
Trip: 3 days
8.3ExcellentShow reviews
Overall 8.3 Excellent
Based on 96 reviews
Boarding
8.0
Comfort
8.0
Crew
8.4
Entertainment
7.0
Food
7.9
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
Excellent 8.0

Breakfast, bars, etcnithin

Nada

YTZ
MDW
Good 6.0

Efficient

Late flight

YTZ
MDW
Excellent 8.3

fast

no TSA precheck

Show more results
*
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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.