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

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 15% of their flights experiencing any sort of delay.

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

As of May 2026, 26 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 15% of weekly flights taking off on this day.

How often are flights from Toronto to Chicago delayed?

Historically, on average around 15% 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.

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 May 2026. The most popular departure time for this route is 8:00a.m., with 53% of flights per day taking off at noon.

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

Thursday 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.

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 1 as of May 2026.

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$ 170 Cheap Flights from Toronto Island Airport to Chicago in 2026

Q: What is the typical price of a round-trip flight between Toronto Island Airport and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from C$ 545 to C$ 250. The lowest price recently found on this route was C$ 276.

1 adult

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.

8:40 p.m. - 9:35 p.m.

YTZ

ORD

1h 55mdirect

11:45 a.m. - 2:25 p.m.

ORD

YTZ

1h 40mdirect

C$ 276Porter Airlines

Sun, 6 Sep - Sun, 13 Sep

1:45 p.m. - 2:35 p.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 277Porter Airlines

Thu, 11 Jun - Sun, 14 Jun

8:40 p.m. - 9:35 p.m.

YTZ

ORD

1h 55mdirect

7:00 a.m. - 9:40 a.m.

ORD

YTZ

1h 40mdirect

C$ 277Porter Airlines

Sun, 13 Sep - Sat, 19 Sep

1:45 p.m. - 2:35 p.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 279Porter Airlines

Mon, 18 May - Wed, 20 May

10:05 a.m. - 11:00 a.m.

YTZ

ORD

1h 55mdirect

7:00 a.m. - 9:40 a.m.

ORD

YTZ

1h 40mdirect

C$ 279Porter Airlines

Sat, 19 Sep - Tue, 22 Sep

1:45 p.m. - 2:35 p.m.

YTZ

MDW

1h 50mdirect

10:15 a.m. - 12:55 p.m.

MDW

YTZ

1h 40mdirect

C$ 280Air Transat

Fri, 29 May - Fri, 5 Jun

8:40 p.m. - 9:35 p.m.

YTZ

ORD

1h 55mdirect

11:45 a.m. - 2:25 p.m.

ORD

YTZ

1h 40mdirect

C$ 280Porter Airlines

Tue, 1 Sep - Sun, 6 Sep

8:45 a.m. - 9:35 a.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 281Porter Airlines

Mon, 15 Jun - Mon, 22 Jun

1:45 p.m. - 2:35 p.m.

YTZ

MDW

1h 50mdirect

3:20 p.m. - 6:00 p.m.

MDW

YTZ

1h 40mdirect

C$ 287Air Transat

Fri, 22 May - Sun, 24 May

12:15 p.m. - 1:10 p.m.

YTZ

ORD

1h 55mdirect

7:25 a.m. - 10:06 a.m.

ORD

YTZ

1h 41mdirect

C$ 289Air Canada

Sun, 14 Jun - Sun, 21 Jun

Porter Airlines flights from Toronto Island Airport to Chicago

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

Porter Airlines

6 Sep

YTZ8:40 p.m.Toronto Island

1h 55m

ORD9:35 p.m.Chicago O'Hare Intl

13 Sep

ORD11:45 a.m.Chicago O'Hare Intl

1h 40m

YTZ2:25 p.m.Toronto Island

C$ 276

Porter Airlines

13 Sep

YTZ8:40 p.m.Toronto Island

1h 55m

ORD9:35 p.m.Chicago O'Hare Intl

19 Sep

ORD7:00 a.m.Chicago O'Hare Intl

1h 40m

YTZ9:40 a.m.Toronto Island

C$ 277

Porter Airlines

19 Sep

YTZ10:05 a.m.Toronto Island

1h 55m

ORD11:00 a.m.Chicago O'Hare Intl

22 Sep

ORD7:00 a.m.Chicago O'Hare Intl

1h 40m

YTZ9:40 a.m.Toronto Island

C$ 279

Air Canada flights from Toronto Island Airport to Chicago

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

Air Canada

14 Jun

YTZ12:15 p.m.Toronto Island

1h 55m

ORD1:10 p.m.Chicago O'Hare Intl

21 Jun

ORD7:25 a.m.Chicago O'Hare Intl

1h 41m

YTZ10:06 a.m.Toronto Island

C$ 289

Air Canada

15 Jun

YTZ7:20 p.m.Toronto Island

1h 56m

ORD8:16 p.m.Chicago O'Hare Intl

16 Sep

ORD2:00 p.m.Chicago O'Hare Intl

1h 41m

YTZ4:41 p.m.Toronto Island

C$ 295

Air Canada

11 Jun

YTZ12:15 p.m.Toronto Island

1h 55m

ORD1:10 p.m.Chicago O'Hare Intl

18 Jun

ORD7:25 a.m.Chicago O'Hare Intl

1h 41m

YTZ10:06 a.m.Toronto Island

C$ 296

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

Cheapest round-trip

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 6/9

8:40 p.m.-9:35 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 13/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 276

Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 14/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 277

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 13/9

8:40 p.m.-9:35 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sat 19/9

7:00 a.m.-9:40 a.m.

Nonstop1h 40m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 18/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 20/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 279

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 19/9

10:05 a.m.-11:00 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Tue 22/9

7:00 a.m.-9:40 a.m.

Nonstop1h 40m

C$ 279

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 29/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Fri 5/6

10:15 a.m.-12:55 p.m.

Nonstop1h 40m

C$ 280

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 1/9

8:40 p.m.-9:35 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 6/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 280

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 15/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

Chicago Midway

Mon 22/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 22/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 24/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 287

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 14/6

12:15 p.m.-1:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sun 21/6

7:25 a.m.-10:06 a.m.

Nonstop1h 41m

C$ 289

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 typical price of a round-trip flight between Toronto Island Airport and Chicago?

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Toronto Island Airport averaging around C$ 109.

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$ 596. 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$ 1,026. 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 morning 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$ 669. Flying to Chicago in the morning 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$ 1,112 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

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$ 150
Fastest flight time	1h 50m
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$ 150. The best round-trip flight deal from Toronto Island Airport to Chicago found on momondo in the last 72 hours is C$ 272.

The fastest flight from Toronto Island Airport to Chicago takes 1h 50m

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

Frequently asked questions about flying from Toronto Island Airport to Chicago

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 50m.
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 1 as of May 2026.
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 (33.15% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (11.11%), Embraer 170 (9.63%), and Embraer 175 (8.48%).
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$ 192	Free Cancellation	Rating 8.0 436 reviews		Search Porter Airlines 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$ 192. Generally, Porter Airlines has 13 flights on this route every week with an average price of C$ 284. Porter Airlines is rated 8.0/10 by our users.

Merrillville

Hammond

Munster

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

Wed 3/6

Wed 10/6

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

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Toronto Island Airport

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Toronto Island Airport to Chicago from C$ 170

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 1/8. 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

Porter Airlines flights from Toronto Island Airport to Chicago

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

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada 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 typical price of a round-trip flight between Toronto Island Airport and Chicago?

What is the cheapest month to fly to Chicago?

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?

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

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

How often are flights from Toronto to Chicago delayed?

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

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

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

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

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

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

Frequently asked questions about flying 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?

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

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Toronto Island Airport

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year