Cheap flights from Toronto Island Airport to Chicago

YTZ — CHI
6 Dec — 13 Dec1
Return
1 adult
Economy
From?
To?
Tue 6/12
Tue 13/12

How to find the cheapest flight from Toronto Island (YTZ) to Chicago (CHI)

All the information you need to plan the best YTZ to CHI flight in 2022: compare Toronto Island to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

YTZ - CHI

Price

C$ 225 - C$ 333

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

Popular inJanuaryHigh demand for flights, 18% potential price rise
Cheapest inJulyBest time to find cheap flights, 18% potential price drop
Round-trip fromC$ 304From Toronto Island to Chicago (CHI)
One-way fromC$ 141One-way flight from Toronto Island to Chicago (CHI)

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

Travellers have found it’s best to book a flight 56 days in advance to save up to 45% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 56 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Toronto Island Airport to Chicago 1-2 weeks in advance for as low as C$ 399, or C$ 488 for flights within the next 24 hours.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, June can be a great choice for travel to Chicago. Flights to Chicago from Toronto Island Airport in June are about C$ 360 on average during June, but can be found for as low as C$ 219.

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

When flying from Toronto Island Airport to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap flights from Toronto Island to Chicago in December, January 2022

The best prices found for YTZ to CHI flights for December, January
20 Dec. - 3 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 229

Porter Airlines

Deal found 28/11

14 Dec. - 19 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 230

Porter Airlines

Deal found 28/11

15 Dec. - 19 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 233

Porter Airlines

Deal found 1/12

Toronto Island to Chicago 2022 flight deals

Cheap flights to Chicago from Toronto Island found for this year
20 Dec. - 3 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 229

Porter Airlines

Deal found 28/11

14 Dec. - 19 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 230

Porter Airlines

Deal found 28/11

15 Dec. - 19 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 233

Porter Airlines

Deal found 1/12

Cheap Air Canada flights from Toronto Island to Chicago

13 Jan. - 15 Jan.
YTZ

Toronto Island

ORD

Chicago O'Hare Intl

1 stop

6h 27m
ORD

Chicago O'Hare Intl

YTZ

Toronto Island

1 stop

6h 29m
C$ 261

Air Canada

Deal found 28/11

17 Feb. - 20 Feb.
YTZ

Toronto Island

ORD

Chicago O'Hare Intl

1 stop

6h 44m
ORD

Chicago O'Hare Intl

YTZ

Toronto Island

1 stop

5h 34m
C$ 279

Air Canada

Deal found 28/11

12 Jan. - 14 Jan.
YTZ

Toronto Island

ORD

Chicago O'Hare Intl

1 stop

6h 27m
ORD

Chicago O'Hare Intl

YTZ

Toronto Island

1 stop

6h 29m
C$ 280

Air Canada

Deal found 28/11

Cheap Porter Airlines flights from Toronto Island to Chicago

20 Dec. - 3 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 229

Porter Airlines

Deal found 28/11

14 Dec. - 19 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 230

Porter Airlines

Deal found 28/11

13 Dec. - 15 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 235

Porter Airlines

Deal found 29/11

Direct flights to Chicago from Toronto Island

Save time with Toronto Island to Chicago direct flight deals
20 Dec. - 3 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 229

Porter Airlines

Deal found 28/11

14 Dec. - 19 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 230

Porter Airlines

Deal found 28/11

15 Dec. - 19 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 233

Porter Airlines

Deal found 1/12

Last minute flights from Toronto Island to Chicago

Late deals on round-trip flights to Chicago from Toronto Island, departing today and this week
11 Dec. - 12 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 254

Porter Airlines

Deal found 28/11

11 Dec. - 15 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 316

Porter Airlines

Deal found 1/12

9 Dec. - 20 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 321

Porter Airlines

Deal found 30/11

One-way flights to Chicago from Toronto Island

The cheapest one-way flights from Toronto Island to Chicago
16 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 141

Porter Airlines

Deal found 1/12

13 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 142

Porter Airlines

Deal found 29/11

15 Dec.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 143

Porter Airlines

Deal found 28/11

Related info for your journey

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

Which airlines flying from Toronto Island to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Toronto Island to Chicago that may be offering flexible cancellation policies are Porter Airlines and Air Canada. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Toronto Island Airport to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto Island Airport to Chicago for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 229, but on average you can expect to pay C$ 254.

Are there direct flights from Toronto Island Airport to Chicago for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Toronto Island Airport to Chicago under C$ 300. A good price for a direct flight from Toronto Island Airport to Chicago is less than C$ 252.

Are there last-minute flights available from Toronto Island Airport to Chicago for under C$ 300?

There are currently 20+ open flights from Toronto Island Airport to Chicago within the next 7 days for less than C$ 300.

What are the cheapest airlines flying from Toronto Island Airport to Chicago round-trip?

According to our current data, Porter Airlines (C$ 229), and Air Canada (C$ 261) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 38% cheaper than the other options available to this destination.

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

While on average a flight from Toronto Island Airport to Chicago is generally C$ 351, our data shows the cheapest flight currently is C$ 351. When looking at the most popular route, (Toronto Island - Chicago Midway), you can expect to pay C$ 238 for that flight.

Other flights to Chicago

Alternative routes for Toronto Island to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Molinefrom C$ 540 pp
Pearson Intl to Peoriafrom C$ 1,385 pp

Top airline flying from Toronto Island to Chicago

The chart below displays the airlines Cheapflights users travelling from Toronto Island to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Porter AirlinesCheapestC$ 238AverageC$ 328FlexibilityNo cancel feeOn-time52%COVID-19 safety
Search Porter Airlines flights

Hourly flight availability from Toronto Island to Chicago

See what time of day planes typically take off from Toronto Island to Chicago
1%of flight departuresEarly morningMidnight to 6 am
33%of flight departuresMorning6 am to noon
66%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 Chicago

See how many times per day planes take to the skies headed from Toronto Island to Chicago
Sunday1daily flight
Monday3daily flights
Tuesday3daily flights
Wednesday3daily flights
Thursday3daily flights
Friday3daily flights
Saturday0daily flights