How many flights depart from Toronto Island Airport to Chicago on average per day?

3 flights are operational daily from Toronto Island Airport to Chicago as of December 2025. The most popular departure time for this route is 9:00a.m., with 63% of flights per day taking off at noon.

What is the cheapest airline that flies from Toronto Island to Chicago?

Porter Airlines and Air Canada are the most popular carriers operating from Toronto Island to Chicago

What is the most punctual flight time for Toronto to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon have, in the past, seen delays more frequently in comparison.

How many flights depart from Toronto Island Airport to Chicago on average per week?

As of December 2025, 24 flights take off from Toronto Island Airport and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

According to our data, Porter Airlines has had the least delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

How often are flights from Toronto to Chicago delayed?

Historically, on average around 14% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 111 minutes.

When did momondo last update prices for flights from Toronto Island Airport to Chicago?

Prices for flights from Toronto Island Airport to Chicago were last updated today.

How many operators does momondo search for flights from Toronto Island Airport to Chicago?

The number of operators available for flights from Toronto Island Airport to Chicago is 2 as of December 2025.

How old do you have to be to fly from Toronto Island Airport to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Toronto Island Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

C$ 160 Cheap Flights from Toronto Island Airport to Chicago in 2025/26

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Toronto Island Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:15 a.m. - 10:05 a.m.

YTZ

MDW

1h 50mdirect

4:15 p.m. - 6:57 p.m.

MDW

YTZ

1h 42mdirect

C$ 252Porter Airlines

Thu, 15 Jan - Sun, 18 Jan

9:15 a.m. - 10:05 a.m.

YTZ

MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.

MDW

YTZ

1h 42mdirect

C$ 255Porter Airlines

Fri, 16 Jan - Fri, 23 Jan

2:30 p.m. - 3:20 p.m.

YTZ

MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.

MDW

YTZ

1h 42mdirect

C$ 256Porter Airlines

Sun, 25 Jan - Mon, 26 Jan

9:15 a.m. - 10:05 a.m.

YTZ

MDW

1h 50mdirect

11:05 a.m. - 1:47 p.m.

MDW

YTZ

1h 42mdirect

C$ 258Porter Airlines

Fri, 16 Jan - Fri, 23 Jan

11:00 a.m. - 11:50 a.m.

YTZ

MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.

MDW

YTZ

1h 42mdirect

C$ 259Porter Airlines

Sat, 24 Jan - Thu, 29 Jan

9:20 a.m. - 10:10 a.m.

YTZ

MDW

1h 50mdirect

11:05 a.m. - 1:47 p.m.

MDW

YTZ

1h 42mdirect

C$ 263Porter Airlines

Thu, 15 Jan - Thu, 29 Jan

3:30 p.m. - 8:10 p.m.

YTZ

ORD

5h 40m1 stop

12:50 p.m. - 7:55 p.m.

ORD

YTZ

6h 05m1 stop

C$ 273Air Canada

Sat, 31 Jan - Sat, 7 Feb

8:30 a.m. - 2:55 p.m.

YTZ

ORD

7h 25m1 stop

7:15 a.m. - 2:55 p.m.

ORD

YTZ

6h 40m1 stop

C$ 274Air Canada

Fri, 16 Jan - Sun, 18 Jan

8:30 a.m. - 2:55 p.m.

YTZ

ORD

7h 25m1 stop

7:15 a.m. - 2:55 p.m.

ORD

YTZ

6h 40m1 stop

C$ 285Air Canada

Thu, 15 Jan - Sun, 18 Jan

2:05 p.m. - 11:46 p.m.

YTZ

ORD

10h 41m2 stops

5:15 a.m. - 10:03 p.m.

ORD

YTZ

15h 48m2 stops

C$ 350Multiple Airlines

Wed, 14 Jan - Wed, 21 Jan

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada deals on Toronto Island Airport to Chicago flight tickets

Air Canada

31 Jan

YTZ3:30 p.m.Toronto Island

5h 40m

1 stop

ORD8:10 p.m.Chicago O'Hare Intl

7 Feb

ORD12:50 p.m.Chicago O'Hare Intl

6h 05m

1 stop

YTZ7:55 p.m.Toronto Island

C$ 273

Find similar

Air Canada

16 Jan

YTZ8:30 a.m.Toronto Island

7h 25m

1 stop

ORD2:55 p.m.Chicago O'Hare Intl

18 Jan

ORD7:15 a.m.Chicago O'Hare Intl

6h 40m

1 stop

YTZ2:55 p.m.Toronto Island

C$ 274

Find similar

Air Canada

15 Jan

YTZ8:30 a.m.Toronto Island

7h 25m

1 stop

ORD2:55 p.m.Chicago O'Hare Intl

18 Jan

ORD7:15 a.m.Chicago O'Hare Intl

6h 40m

1 stop

YTZ2:55 p.m.Toronto Island

C$ 285

Find similar

Porter Airlines flights from Toronto Island Airport to Chicago

Our best Porter Airlines deals on Toronto Island Airport to Chicago flight tickets

Porter Airlines

15 Jan

YTZ9:15 a.m.Toronto Island

1h 50m

MDW10:05 a.m.Chicago Midway

18 Jan

MDW4:15 p.m.Chicago Midway

1h 42m

YTZ6:57 p.m.Toronto Island

C$ 252

Find similar

Porter Airlines

16 Jan

YTZ9:15 a.m.Toronto Island

1h 50m

MDW10:05 a.m.Chicago Midway

23 Jan

MDW11:00 a.m.Chicago Midway

1h 42m

YTZ1:42 p.m.Toronto Island

C$ 255

Find similar

Porter Airlines

25 Jan

YTZ2:30 p.m.Toronto Island

1h 50m

MDW3:20 p.m.Chicago Midway

26 Jan

MDW11:00 a.m.Chicago Midway

1h 42m

YTZ1:42 p.m.Toronto Island

C$ 256

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Toronto Island Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 15/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Sun 18/1

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 16/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Fri 23/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 25/1

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 26/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 16/1

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Fri 23/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 24/1

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Thu 29/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 259

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 15/1

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Thu 29/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 263

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 31/1

3:30 p.m.-8:10 p.m.

1 stop5h 40m

Chicago O'Hare Intl

Sat 7/2

12:50 p.m.-7:55 p.m.

1 stop6h 05m

C$ 273

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 16/1

8:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Sun 18/1

7:15 a.m.-2:55 p.m.

1 stop6h 40m

C$ 274

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 15/1

8:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Sun 18/1

7:15 a.m.-2:55 p.m.

1 stop6h 40m

C$ 285

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 14/1

2:05 p.m.-11:46 p.m.

2 stops10h 41m

Chicago O'Hare Intl

Wed 21/1

5:15 a.m.-10:03 p.m.

2 stops15h 48m

C$ 350

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Toronto Island Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

What is the cheapest month to fly to Chicago?

The month of September is another great option to travel to Chicago, with average flight prices from Toronto Island Airport averaging around C$ 231.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 586. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,048. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Toronto Island Airport to Chicago when you can find flight prices for as low as C$ 627. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,082 per ticket.

What is the cheapest Toronto Island to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto Island - Chicago flight prices

What cabin class options are available on Toronto Island to Chicago flights?

There is only 1 cabin class available to choose from on Toronto Island to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto Island Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto Island Airport to Chicago.

When to book flights from Toronto Island Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Island Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Toronto Island Airport to Chicago (YTZ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Island Airport to Chicago

Best price found	C$ 152
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Toronto Island Airport in the past 72 hours is C$ 152. The best round-trip flight deal from Toronto Island Airport to Chicago found on momondo in the last 72 hours is C$ 245.

The fastest flight from Toronto Island Airport to Chicago takes 1h 49m

Direct flights go from Toronto Island Airport to Chicago every day.

There are 3 airports in Chicago. From Toronto Island Airport there are direct flights to Chicago Midway (MDW).

Search flight deals

How far is Toronto Island to Chicago by plane?
The straight-line distance from Toronto Island to Chicago is 698.8 km. A reasonable flight in good conditions will take 1h 49m.
When did momondo last update prices for flights from Toronto Island Airport to Chicago?
Prices for flights from Toronto Island Airport to Chicago were last updated today.
How many operators does momondo search for flights from Toronto Island Airport to Chicago?
The number of operators available for flights from Toronto Island Airport to Chicago is 2 as of December 2025.
How old do you have to be to fly from Toronto Island Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Toronto Island Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Toronto Island Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Toronto Island Airport to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q (30.88% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (15.20%), Boeing 737-800 (12.93%), and Embraer 175 (11.76%).
What is the most popular airline from Toronto Island Airport to Chicago?
momondo data reveals that the most frequently booked airline on the route from Toronto Island Airport to Chicago is Porter Airlines, representing 100% of all bookings.

Best airlines flying from Toronto Island Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Island Airport to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 195	Free Cancellation	Rating 8.0 399 reviews		Search Porter Airlines flights
Air Canada	PriceFrom C$ 305	Free Cancellation	Rating 7.1 10,534 reviews		Search Air Canada flights

Porter Airlines Flights From Toronto Island Airport to Chicago
The lowest priced Porter Airlines flight from Toronto Island Airport to Chicago from the last 72 hours was C$ 195. Generally, Porter Airlines has 12 flights on this route every week with an average price of C$ 286. Porter Airlines is rated 8.0/10 by our users.

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Toronto to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Toronto are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sat 17/1

Sat 24/1

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Popular Cities in the United States

Flights to Fort Lauderdalefrom C$ 153

Flights to Orlandofrom C$ 158

Flights to New Yorkfrom C$ 256

Flights to Las Vegasfrom C$ 125

Flights to Los Angelesfrom C$ 158

Flights to Miamifrom C$ 285

Flights to San Franciscofrom C$ 125

Flights to Honolulufrom C$ 331

Flights to Phoenixfrom C$ 154

Flights to Tampafrom C$ 212

Flights to Houstonfrom C$ 197

Flights to Seattlefrom C$ 192

Cheap flights from Toronto Island Airport to Chicago from C$ 160

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto Island Airport to Chicago departing on 18/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Toronto Island Airport to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada deals on Toronto Island Airport to Chicago flight tickets

Porter Airlines flights from Toronto Island Airport to Chicago

Our best Porter Airlines deals on Toronto Island Airport to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Toronto Island Airport to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto Island Airport to Chicago

What is the cheapest month to fly to Chicago?

The month of September is another great option to travel to Chicago, with average flight prices from Toronto Island Airport averaging around C$ 231.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Toronto Island to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto Island - Chicago flight prices

What cabin class options are available on Toronto Island to Chicago flights?

There is only 1 cabin class available to choose from on Toronto Island to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Toronto Island Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto Island Airport to Chicago.

What is the cheapest airline that flies from Toronto Island to Chicago?

Porter Airlines and Air Canada are the most popular carriers operating from Toronto Island to Chicago

How often are flights from Toronto to Chicago delayed?

Historically, on average around 14% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 111 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Wednesday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

According to our data, Porter Airlines has had the least delays on this route over the last 12 months, with about 14% of their flights experiencing any sort of delay.

How many flights depart from Toronto Island Airport to Chicago on average per day?

3 flights are operational daily from Toronto Island Airport to Chicago as of December 2025. The most popular departure time for this route is 9:00a.m., with 63% of flights per day taking off at noon.

How many flights depart from Toronto Island Airport to Chicago on average per week?

As of December 2025, 24 flights take off from Toronto Island Airport and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

When to book flights from Toronto Island Airport to Chicago

Cheap Toronto Island Airport to Chicago (YTZ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Island Airport to Chicago

Best price found

Fastest flight time

Direct flights

Airports in Chicago

How far is Toronto Island to Chicago by plane?

When did momondo last update prices for flights from Toronto Island Airport to Chicago?

How many operators does momondo search for flights from Toronto Island Airport to Chicago?

How old do you have to be to fly from Toronto Island Airport to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Toronto Island Airport to Chicago?

What is the most popular airline from Toronto Island Airport to Chicago?

Best airlines flying from Toronto Island Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Island Airport to Chicago with momondo

Porter Airlines Flights From Toronto Island Airport to Chicago

Travelling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Toronto to Chicago?

Can I find flights from Toronto to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Toronto to Chicago?

I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago