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

Air Transat, Porter Airlines, and Air Canada are the most popular carriers operating from Toronto Island to Illinois

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

As of September 2026, 32 flights take off from Toronto Island Airport and land in Illinois each week. The most common flight departure day for this route is Mon, with 25% of weekly flights taking off on this day.

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

As of September 2026, there are 4 flights per day flying from Toronto Island Airport to Illinois. The most common time of day flights depart is 10:00a.m., with 50% of flights taking off in the afternoon.

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

Prices for flights from Toronto Island Airport to Illinois are refreshed on a daily basis.

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

The number of operators available for flights from Toronto Island Airport to Illinois is 2 as of September 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Island Airport to Illinois.

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

The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 244 Cheap Flights from Toronto Island Airport to Illinois in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Toronto Island Airport to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 388Air Transat

Fri, 20 Nov - Sat, 21 Nov

10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

12:20 p.m. - 3:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 404Porter Airlines

Fri, 30 Oct - Sun, 1 Nov

10:10 a.m. - 11:00 a.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 409Porter Airlines

Fri, 23 Oct - Fri, 23 Oct

4:35 p.m. - 5:40 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 443Porter Airlines

Sat, 28 Nov - Tue, 1 Dec

10:45 a.m. - 2:52 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

5h 07m1 stop Montreal Pierre Elliott Trudeau Intl

1:55 p.m. - 4:42 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mdirect

C$ 460Air Canada

Sat, 14 Nov - Wed, 18 Nov

10:45 a.m. - 3:02 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

5h 17m1 stop Montreal Pierre Elliott Trudeau Intl

1:55 p.m. - 4:42 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mdirect

C$ 460Air Canada

Wed, 25 Nov - Sat, 28 Nov

10:10 a.m. - 11:00 a.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 460Multiple Airlines

Sat, 10 Oct - Sat, 17 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 460Multiple Airlines

Tue, 20 Oct - Fri, 23 Oct

10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

12:20 p.m. - 3:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 460Air Transat

Fri, 8 Jan - Sun, 10 Jan

6:50 a.m. - 8:12 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

14h 22m1 stop Montreal Pierre Elliott Trudeau Intl

2:00 p.m. - 4:48 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 463Air Canada

Sat, 10 Oct - Sun, 11 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 408Porter Airlines

Sat, 3 Oct - Mon, 5 Oct

12:15 p.m. - 1:25 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mdirect

2:00 p.m. - 4:48 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 423Air Canada

Sat, 3 Oct - Mon, 5 Oct

10:10 a.m. - 11:00 a.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 513Porter Airlines

Wed, 30 Sep - Mon, 5 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 582Porter Airlines

Tue, 29 Sep - Tue, 13 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

6:16 a.m. - 9:58 p.m.MDW Chicago Midway-YTZ Toronto Island

38h 42m3 stops Atlanta Hartsfield-Jackson Fort Lauderdale Ottawa

C$ 589Multiple Airlines

Tue, 29 Sep - Wed, 28 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 595Porter Airlines

Fri, 2 Oct - Fri, 9 Oct

9:30 a.m. - 2:52 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

6h 22m1 stop Montreal Pierre Elliott Trudeau Intl

1:55 p.m. - 4:42 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mdirect

C$ 626Air Canada

Tue, 29 Sep - Wed, 28 Oct

9:30 a.m. - 2:52 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

6h 22m1 stop Montreal Pierre Elliott Trudeau Intl

7:05 a.m. - 2:21 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

6h 16m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 630Air Canada

Tue, 29 Sep - Wed, 28 Oct

10:10 a.m. - 11:00 a.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 729Multiple Airlines

Sat, 3 Oct - Tue, 6 Oct

12:20 p.m. - 1:30 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 10mdirect

2:05 p.m. - 4:53 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 48mdirect

C$ 735Jazz

Sat, 3 Oct - Wed, 7 Oct

Cheap direct flights

Enter your travel dates to find the best prices.

10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 388Air Transat

Fri, 20 Nov - Sat, 21 Nov

10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

12:20 p.m. - 3:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 404Porter Airlines

Fri, 30 Oct - Sun, 1 Nov

10:10 a.m. - 11:00 a.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 409Porter Airlines

Fri, 23 Oct - Fri, 23 Oct

4:35 p.m. - 5:40 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

6:20 p.m. - 9:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 443Porter Airlines

Sat, 28 Nov - Tue, 1 Dec

10:10 a.m. - 11:00 a.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 460Multiple Airlines

Sat, 10 Oct - Sat, 17 Oct

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

3:20 p.m. - 6:00 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 460Multiple Airlines

Tue, 20 Oct - Fri, 23 Oct

10:35 a.m. - 11:40 a.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 05mdirect

12:20 p.m. - 3:06 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 46mdirect

C$ 460Air Transat

Fri, 8 Jan - Sun, 10 Jan

1:45 p.m. - 2:35 p.m.YTZ Toronto Island-MDW Chicago Midway

1h 50mdirect

11:45 a.m. - 2:25 p.m.MDW Chicago Midway-YTZ Toronto Island

1h 40mdirect

C$ 462Porter Airlines

Tue, 13 Oct - Tue, 20 Oct

12:05 p.m. - 1:20 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 15mdirect

1:55 p.m. - 4:42 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mdirect

C$ 480Air Canada

Sat, 14 Nov - Wed, 18 Nov

12:05 p.m. - 1:20 p.m.YTZ Toronto Island-ORD Chicago O'Hare Intl

2h 15mdirect

1:55 p.m. - 4:42 p.m.ORD Chicago O'Hare Intl-YTZ Toronto Island

1h 47mdirect

C$ 482Air Canada

Wed, 25 Nov - Sat, 28 Nov

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Air Transat flights from Toronto Island Airport to Illinois

Our best Air Transat deals on Toronto Island Airport to Illinois flight tickets

Air Transat

20 Nov

YTZ10:35 a.m.Toronto Island

2h 05m

ORD11:40 a.m.Chicago O'Hare Intl

21 Nov

ORD6:20 p.m.Chicago O'Hare Intl

1h 46m

YTZ9:06 p.m.Toronto Island

C$ 388

Air Transat

20 Nov

YTZ4:35 p.m.Toronto Island

2h 05m

ORD5:40 p.m.Chicago O'Hare Intl

22 Nov

ORD12:20 p.m.Chicago O'Hare Intl

1h 46m

YTZ3:06 p.m.Toronto Island

C$ 469

Air Canada flights from Toronto Island Airport to Illinois

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

Air Canada

3 Oct

YTZ12:15 p.m.Toronto Island

2h 10m

ORD1:25 p.m.Chicago O'Hare Intl

5 Oct

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

1h 48m

YTZ4:48 p.m.Toronto Island

C$ 423

Air Canada

14 Nov

YTZ10:45 a.m.Toronto Island

5h 07m

1 stop

ORD2:52 p.m.Chicago O'Hare Intl

18 Nov

ORD1:55 p.m.Chicago O'Hare Intl

1h 47m

YTZ4:42 p.m.Toronto Island

C$ 460

Air Canada

10 Oct

YTZ6:50 a.m.Toronto Island

14h 22m

1 stop

ORD8:12 p.m.Chicago O'Hare Intl

11 Oct

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

1h 48m

YTZ4:48 p.m.Toronto Island

C$ 463

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 20/11

10:35 a.m.-11:40 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sat 21/11

6:20 p.m.-9:06 p.m.

Nonstop1h 46m

C$ 388

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 30/10

10:35 a.m.-11:40 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 1/11

12:20 p.m.-3:06 p.m.

Nonstop1h 46m

C$ 404

Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 23/10

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

Nonstop1h 50m

Chicago Midway

Fri 23/10

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

Nonstop1h 40m

C$ 409

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 28/11

4:35 p.m.-5:40 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 1/12

6:20 p.m.-9:06 p.m.

Nonstop1h 46m

C$ 443

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 14/11

10:45 a.m.-2:52 p.m.

1 stop5h 07m

Chicago O'Hare Intl

Wed 18/11

1:55 p.m.-4:42 p.m.

Nonstop1h 47m

C$ 460

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 25/11

10:45 a.m.-3:02 p.m.

1 stop5h 17m

Chicago O'Hare Intl

Sat 28/11

1:55 p.m.-4:42 p.m.

Nonstop1h 47m

C$ 460

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 10/10

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

Nonstop1h 50m

Chicago Midway

Sat 17/10

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

Nonstop1h 40m

C$ 460

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 20/10

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

Nonstop1h 50m

Chicago Midway

Fri 23/10

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

Nonstop1h 40m

C$ 460

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 8/1

10:35 a.m.-11:40 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 10/1

12:20 p.m.-3:06 p.m.

Nonstop1h 46m

C$ 460

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sat 10/10

6:50 a.m.-8:12 p.m.

1 stop14h 22m

Chicago O'Hare Intl

Sun 11/10

2:00 p.m.-4:48 p.m.

Nonstop1h 48m

C$ 463

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 Illinois

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

Other information

What is the cheapest month to fly to Illinois?

In general, January is the cheapest month to fly from Toronto Island Airport to Illinois. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 310. If you don’t want to visit Illinois in January, then you should wait until December to fly from Toronto Island Airport, when ticket prices are also cheap, with an average price of C$ 313.

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

According to our data, Thursday is the cheapest day to fly to Illinois from Toronto Island Airport. The lowest ticket price found for a Thursday departure recently was C$ 354. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Illinois is Sunday, with ticket prices averaging around C$ 520.

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

Our most recent data shows that the best time of day to fly to Illinois is at noon. Flights from Toronto Island Airport to Illinois during this time can be as low as C$ 339. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are C$ 558 on average. Flights to Illinois from Toronto Island Airport in the evening are generally more expensive because this time of day is more convenient for travellers’ schedules.

What is the cheapest Toronto Island to Illinois flight route?

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

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

There are 3 cabin classes available to choose from on Toronto Island Airport to Illinois 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 Illinois flights?

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

Cheap Toronto Island Airport to Illinois flight deals and tips

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

Best price found	C$ 244
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Toronto Island Airport in the past 72 hours is C$ 244. The best round-trip flight deal from Toronto Island Airport to Illinois found on momondo in the last 72 hours is C$ 388.

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

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

There are 98 airports in Illinois. 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 Illinois

When did momondo last update prices for flights from Toronto Island Airport to Illinois?
Prices for flights from Toronto Island Airport to Illinois are refreshed on a daily basis.
How many operators does momondo search for flights from Toronto Island Airport to Illinois?
The number of operators available for flights from Toronto Island Airport to Illinois is 2 as of September 2026.
How old do you have to be to fly from Toronto Island Airport to Illinois?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Island Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Toronto Island Airport to Illinois?
momondo data reveals that the most frequently booked plane model on the route from Toronto Island Airport to Illinois is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 41.04% of all bookings. The subsequent popular models are Boeing 737-900 at 8.62%, Embraer 175 (Enhanced Winglets) at 8.07%, and Embraer 175 at 6.95%.

Best airlines flying from Toronto Island Airport to Illinois

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

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 137	Free Cancellation	Rating 7.1 11,703 reviews		Search Air Canada flights
Porter Airlines	PriceFrom C$ 253	Free Cancellation	Rating 8.0 465 reviews		Search Porter Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Toronto to Illinois for you.

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

Yes. momondo enables you to select and highlight flights to Illinois from Toronto with this policy.

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

Once you have performed a search for Toronto to Illinois flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Illinois 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.