Cheap flights from Toronto Island Airport to Chicago Midway Airport from C$ 200

This is the cheapest one-way flight price, found on 20/9. Prices may vary by date and flight preferences.
YTZ — MDW
26 Sep — 3 Oct1
1 adult
Economy
From?
To?
Tue 26/9
Tue 3/10

How to find the cheapest flight from Toronto Island (YTZ) to Midway (MDW)

All the information you need to plan the best YTZ to MDW flight in 2023: compare Toronto Island to Midway flight prices with the expected peak season, weather and rainfall in Midway.

Popular in

April

Cheapest in

January

Round-trip from

C$ 464

One-way from

C$ 200
High demand for flights, 24% potential price rise
Best time to find cheap flights, 15% potential price drop
From Toronto Island to Chicago Midway
One-way flight from Toronto Island to Chicago Midway

YTZ - CHI

Price

C$ 345 - C$ 611

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

How far in advance should I book a flight from Toronto Island Airport to Chicago Midway Airport?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 60 days in advance, which can save you up to 49% on flights from Toronto Island Airport to Chicago Midway Airport compared to booking the week you need them. Waiting 60 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at C$ 388. For sooner than that we have options available in the next 3 days from C$ 492.

What is the cheapest month to fly from Toronto Island Airport to Chicago Midway Airport?

Our data shows that June tends to be the cheapest month to fly to Chicago Midway Airport from Toronto Island Airport. Users have commonly found prices around C$ 342 for the month, but tickets can be as low as C$ 218. Due to multiple factors, prepare for potentially higher prices in March.

When is the cheapest time to fly from Toronto Island Airport to Chicago Midway Airport (YTZ - MDW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Toronto Island Airport to Chicago Midway Airport as you normally would.

Cheap Porter Airlines flights from Toronto Island to Midway

Cheap Toronto Island to Midway flights in September & October 2023

The best prices found for YTZ to MDW flights for September, October

Toronto Island to Midway 2023 flight deals

Cheap flights to Midway from Toronto Island found for this year

Direct flights to Midway from Toronto Island

Save time with Toronto Island to Midway direct flight deals

Toronto Island to Midway flights leaving soon

Late deals on round-trip flights to Midway from Toronto Island, departing today and this week

One-way flights to Midway from Toronto Island

The cheapest one-way flights from Toronto Island to Midway

Find flights from Toronto Island to Midway within your budget

Use the slider to find flights from Toronto Island to Midway that fit your budget.

Fly from

Any airport

Fly to

Any airport

Budget

C$ 352 - C$ 577

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/10

Nonstop1h 47m

Chicago Midway

Mon 16/10

Nonstop1h 42m

C$ 352

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/10

Nonstop1h 47m

Chicago Midway

Sat 14/10

Nonstop1h 42m

C$ 354

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/11

Nonstop1h 50m

Chicago Midway

Mon 20/11

Nonstop1h 42m

C$ 355

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/10

Nonstop1h 47m

Chicago Midway

Sat 21/10

Nonstop1h 42m

C$ 356

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/10

Nonstop1h 47m

Chicago Midway

Mon 23/10

Nonstop1h 42m

C$ 359

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/11

Nonstop1h 50m

Chicago Midway

Sun 5/11

Nonstop1h 42m

C$ 368

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/10

Nonstop1h 47m

Chicago Midway

Sat 14/10

Nonstop1h 42m

C$ 370

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/10

2 stops14h 07m

Chicago Midway

Tue 24/10

Nonstop1h 42m

C$ 526

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/10

Nonstop1h 47m

Chicago Midway

Sat 14/10

2 stops9h 45m

C$ 577

Flights are sorted by cheapest first

Deals found on 19/9

Reviews of airlines servicing Midway

Porter Airlines
7.6
Good
27 reviews

Comfort

7.7

Boarding

7.6

Food

7.2

Overall

7.6

Crew

8.9

Entertainment

6.3

Reviews

1 / 10

cancelled flight, no assistance, went from direct flight at 1pm to a 645 AM non-direct flight, tried to change and the customer support would not help, refused to give me a manager when I requested to speak with one, then spent an hour on the tarmac. Will do my very best to avoid using this airline again

Porter Airlines
7.6
Good
27 reviews
Porter Airlines
7.6
Good
27 reviews

Comfort

7.7

Boarding

7.6

Food

7.2

Overall

7.6

Crew

8.9

Entertainment

6.3

Reviews

1 / 10

cancelled flight, no assistance, went from direct flight at 1pm to a 645 AM non-direct flight, tried to change and the customer support would not help, refused to give me a manager when I requested to speak with one, then spent an hour on the tarmac. Will do my very best to avoid using this airline again

Related info for your journey

Useful info, stats and facts about Toronto Island to Midway flights.

Can I find flights from Toronto Island Airport to Chicago Midway Airport for under C$ 400 on Cheapflights?

Yes, there are multiple flights from Toronto Island Airport to Chicago Midway Airport for under C$ 400. The cheapest flight booked recently is on Porter Airlines for just C$ 352, but on average you can expect to pay C$ 376.

Are there direct flights from Toronto Island Airport to Chicago Midway Airport for under C$ 400 on Cheapflights?

Cheapflights has 20 direct flights from Toronto Island Airport to Chicago Midway Airport under C$ 400. A good price for a direct flight from Toronto Island Airport to Chicago Midway Airport is less than C$ 376.

Are there last-minute flights available from Toronto Island Airport to Chicago Midway Airport for under C$ 600?

There are currently 20+ open flights from Toronto Island Airport to Chicago Midway Airport within the next 7 days for less than C$ 600.

What is the cheapest airline to fly from Toronto Island Airport to Chicago Midway Airport round-trip?

According to our current data, Porter Airlines (C$ 352), offers the cheapest pricing from Toronto Island Airport to Chicago Midway Airport.

What are the cheapest flights from Toronto Island Airport to Chicago Midway Airport?

On average you can expect to pay C$ 523 for a flight from Toronto Island Airport to Chicago Midway Airport. The cheapest flight overall is C$ 187 while the most popular route, (Toronto Island - Chicago Midway) is currently priced at C$ 341.

What does YTZ to MDW mean?

These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Toronto Island Airport to Chicago Midway Airport flight would often be abbreviated as a YTZ to MDW flight.

Alternative routes for Toronto Island to Midway

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Toronto Island to Midway

The chart below displays the airlines Cheapflights users travelling from Toronto Island to Midway choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 240AverageC$ 362FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Hourly flight availability from Toronto Island to Midway

See what time of day planes typically take off from Toronto Island to Midway
1%of flight departuresEarly morningMidnight to 6 am
45%of flight departuresMorning6 am to noon
54%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Toronto Island to Midway

See how many times per day planes take to the skies headed from Toronto Island to Midway
Sunday1daily flight
Monday2daily flights
Tuesday2daily flights
Wednesday2daily flights
Thursday3daily flights
Friday3daily flights
Saturday1daily flight
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