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Cheap flights from Toronto Island Airport to Illinois from $116

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 Illinois departing on 1/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Toronto Island Airport to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pm
MDW
-
YTZ
1h 42mnonstop
$183Porter Airlines
Thu, Jan 15 - Sun, Jan 18
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$185Porter Airlines
Fri, Jan 16 - Fri, Jan 23
Porter Airlines Logo
2:30 pm - 3:20 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$186Porter Airlines
Sun, Jan 25 - Mon, Jan 26
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
$187Porter Airlines
Fri, Jan 16 - Fri, Jan 23
Porter Airlines Logo
11:00 am - 11:50 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$188Porter Airlines
Sat, Jan 24 - Thu, Jan 29
Porter Airlines Logo
9:20 am - 10:10 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
$191Porter Airlines
Thu, Jan 15 - Thu, Jan 29
Air Canada Logo
3:30 pm - 8:10 pm
YTZ
-
ORD
5h 40m1 stop
Air Canada Logo
12:50 pm - 7:55 pm
ORD
-
YTZ
6h 05m1 stop
$198Air Canada
Sat, Jan 31 - Sat, Feb 7
Air Canada Logo
8:30 am - 2:55 pm
YTZ
-
ORD
7h 25m1 stop
Air Canada Logo
7:15 am - 2:55 pm
ORD
-
YTZ
6h 40m1 stop
$199Air Canada
Fri, Jan 16 - Sun, Jan 18
Air Canada Logo
8:30 am - 2:55 pm
YTZ
-
ORD
7h 25m1 stop
Air Canada Logo
7:15 am - 2:55 pm
ORD
-
YTZ
6h 40m1 stop
$207Air Canada
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
2:05 pm - 11:46 pm
YTZ
-
ORD
10h 41m2 stops
Multiple Airlines Logo
5:15 am - 10:03 pm
ORD
-
YTZ
15h 48m2 stops
$254Multiple Airlines
Wed, Jan 14 - Wed, Jan 21

Air Canada flights from Toronto Island Airport to Illinois

Our best Air Canada deals on Toronto Island Airport to Illinois flight tickets
Air Canada
Jan 31
YTZ3:30 pmToronto Island
5h 40m
1 stop
ORD8:10 pmChicago O'Hare Intl
Feb 7
ORD12:50 pmChicago O'Hare Intl
6h 05m
1 stop
YTZ7:55 pmToronto Island
$198
Find similar
Air Canada
Jan 16
YTZ8:30 amToronto Island
7h 25m
1 stop
ORD2:55 pmChicago O'Hare Intl
Jan 18
ORD7:15 amChicago O'Hare Intl
6h 40m
1 stop
YTZ2:55 pmToronto Island
$199
Find similar
Air Canada
Jan 15
YTZ8:30 amToronto Island
7h 25m
1 stop
ORD2:55 pmChicago O'Hare Intl
Jan 18
ORD7:15 amChicago O'Hare Intl
6h 40m
1 stop
YTZ2:55 pmToronto Island
$207
Find similar

Porter Airlines flights from Toronto Island Airport to Illinois

Our best Porter Airlines deals on Toronto Island Airport to Illinois flight tickets
Porter Airlines
Jan 15
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
Jan 18
MDW4:15 pmChicago Midway
1h 42m
YTZ6:57 pmToronto Island
$183
Find similar
Porter Airlines
Jan 16
YTZ9:15 amToronto Island
1h 50m
MDW10:05 amChicago Midway
Jan 23
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$185
Find similar
Porter Airlines
Jan 25
YTZ2:30 pmToronto Island
1h 50m
MDW3:20 pmChicago Midway
Jan 26
MDW11:00 amChicago Midway
1h 42m
YTZ1:42 pmToronto Island
$186
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Island Airport to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 18, 2025.
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

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/15

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 1/18

4:15 pm-6:57 pm

Nonstop1h 42m

$183

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 1/23

11:00 am-1:42 pm

Nonstop1h 42m

$185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 1/26

11:00 am-1:42 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 1/23

11:05 am-1:47 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 1/24

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:00 am-1:42 pm

Nonstop1h 42m

$188

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/15

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:05 am-1:47 pm

Nonstop1h 42m

$191

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 1/31

3:30 pm-8:10 pm

1 stop5h 40m

Chicago O'Hare Intl

Sat 2/7

12:50 pm-7:55 pm

1 stop6h 05m

$198

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 1/16

8:30 am-2:55 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 1/18

7:15 am-2:55 pm

1 stop6h 40m

$199

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 1/15

8:30 am-2:55 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 1/18

7:15 am-2:55 pm

1 stop6h 40m

$207

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 1/14

2:05 pm-11:46 pm

2 stops10h 41m

Chicago O'Hare Intl

Wed 1/21

5:15 am-10:03 pm

2 stops15h 48m

$254

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

See travel insights to Illinois from

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

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Toronto Island Airport is in August. Flight prices, which tend to average around $168, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $168.

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

The cheapest day to depart from Toronto Island Airport to Illinois is on a Wednesday when prices can be found for as low as $208. Flights from Toronto Island Airport to Illinois on a Thursday will generally be more expensive and average around $291. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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 in the afternoon. Flights from Toronto Island Airport to Illinois during this time can be as low as $236. Flights at noon are often more expensive with an average ticket price of $327.

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 to Illinois flights?

There are 4 cabin classes available to choose from on Toronto Island 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

$117

Fastest flight time

1h 49m

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 $117. The best round-trip flight deal from Toronto Island Airport to Illinois found on momondo in the last 72 hours is $210.
The fastest flight from Toronto Island Airport to Illinois takes 1h 49m
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

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

    Prices for flights from Toronto Island Airport to Illinois are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 you'll need for your trip to Illinois 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 Illinois. 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 Illinois?

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
Porter AirlinesPriceFrom $158Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights

Why use momondo?

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

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 Illinois from Toronto.

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

momondo does allow users to show only those flights to Illinois from Toronto which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Toronto to Illinois.

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.

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