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Cheap flights from Toronto Island Airport to Chicago from $136

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 10/20. 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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Find the cheapest flights from Toronto Island Airport to Chicago

Cheap round-trip flights

Multiple Airlines Logo
7:30 pm - 11:25 pmYTZ-MDW
4h 55m1 stop
Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$234Multiple Airlines
Find Deal
Tue, Oct 14 - Wed, Oct 22
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$240Porter Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$241Porter Airlines
Find Deal
Thu, Oct 16 - Sun, Oct 19
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$243Porter Airlines
Find Deal
Sat, Oct 18 - Mon, Oct 20
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
$244Porter Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
7:30 pm - 11:25 pmYTZ-MDW
4h 55m1 stop
Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$246Multiple Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Air Canada Logo
3:25 pm - 8:17 pmYTZ-ORD
5h 52m1 stop
Air Canada Logo
8:40 am - 2:45 pmORD-YTZ
5h 05m1 stop
$251Air Canada
Find Deal
Sat, Oct 18 - Sat, Oct 25
Air Canada Logo
3:25 pm - 8:06 pmYTZ-ORD
5h 41m1 stop
Air Canada Logo
8:40 am - 4:45 pmORD-YTZ
7h 05m1 stop
$265Air Canada
Find Deal
Sat, Oct 4 - Mon, Oct 6
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$281Air Transat
Find Deal
Sun, Oct 5 - Tue, Oct 7
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$289Air Transat
Find Deal
Fri, Oct 17 - Sun, Oct 19

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada deals on Toronto Island Airport to Chicago flight tickets
Air Canada
Oct 18
YTZ3:25 pmToronto Island
5h 52m
1 stop
ORD8:17 pmChicago O'Hare Intl
Oct 25
ORD8:40 amChicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 pmToronto Island
$251
Find similar
Air Canada
Oct 4
YTZ3:25 pmToronto Island
5h 41m
1 stop
ORD8:06 pmChicago O'Hare Intl
Oct 6
ORD8:40 amChicago O'Hare Intl
7h 05m
1 stop
YTZ4:45 pmToronto Island
$265
Find similar
Air Canada
Oct 18
YTZ3:25 pmToronto Island
5h 52m
1 stop
ORD8:17 pmChicago O'Hare Intl
Oct 19
ORD8:40 amChicago O'Hare Intl
5h 05m
1 stop
YTZ2:45 pmToronto Island
$278
Find similar

Air Transat flights from Toronto Island Airport to Chicago

Our best Air Transat deals on Toronto Island Airport to Chicago flight tickets
Air Transat
Oct 5
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
Oct 7
MDW5:20 pmChicago Midway
1h 42m
YTZ8:02 pmToronto Island
$281
Find similar
Air Transat
Oct 17
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
Oct 19
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
$289
Find similar
Air Transat
Oct 16
YTZ7:50 amToronto Island
1h 49m
MDW8:39 amChicago Midway
Oct 20
MDW9:35 amChicago Midway
1h 42m
YTZ12:17 pmToronto Island
$297
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Island Airport to Chicago 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 September 16, 2025.
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

Tue 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

Wed 10/22

9:35 am-12:17 pm

Nonstop1h 42m

$234

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 10/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sat 10/25

9:35 am-12:17 pm

Nonstop1h 42m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Sun 10/19

9:35 am-12:17 pm

Nonstop1h 42m

$241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 10/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 10/20

9:35 am-12:17 pm

Nonstop1h 42m

$243

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/6

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 11/9

11:00 am-1:42 pm

Nonstop1h 42m

$244

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 10/14

7:30 pm-11:25 pm

1 stop4h 55m

Chicago Midway

Tue 10/21

9:35 am-12:17 pm

Nonstop1h 42m

$246

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/18

3:25 pm-8:17 pm

1 stop5h 52m

Chicago O'Hare Intl

Sat 10/25

8:40 am-2:45 pm

1 stop5h 05m

$251

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/4

3:25 pm-8:06 pm

1 stop5h 41m

Chicago O'Hare Intl

Mon 10/6

8:40 am-4:45 pm

1 stop7h 05m

$265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 10/5

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Tue 10/7

5:20 pm-8:02 pm

Nonstop1h 42m

$281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 10/17

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sun 10/19

9:35 am-12:17 pm

Nonstop1h 42m

$289

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Toronto Island Airport, with most prices found around $160. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Toronto Island Airport to Chicago during August average around $168.

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 $396. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Island Airport to Chicago for around $621.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Toronto Island Airport to Chicago during this time can be as low as $391. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $575.

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 are 4 cabin classes 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?

You could potentially save up to 12% on your flight if you consider stops on a Toronto Island Airport to Chicago flight.

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

$179

Fastest flight time

1h 49m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Toronto Island Airport in the past 72 hours is $179. The best round-trip flight deal from Toronto Island Airport to Chicago found on momondo in the last 72 hours is $181.
The fastest flight from Toronto Island Airport to Chicago takes 1h 49m
Direct flights go from Toronto Island Airport to Chicago every day.
There is 1 airport near Chicago: 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 434.2 mi. By plane, this route typically takes 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 are updated daily.

  • 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?

    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 Chicago.

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

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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?

  • 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
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom $158Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights

  • Porter Airlines Flights From Toronto Island Airport to Chicago

    Porter Airlines flight deals from Toronto Island Airport to Chicago start from $158 round-trip. Over the 11 Porter Airlines flights for this route in a normal week, average airfare is usually $258 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Toronto to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

momondo does allow users to show only those flights to Chicago 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 Chicago?

momondo helps you find the best flight between Toronto and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.

An easier way to manage your Chicago trip

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Thu 10/16
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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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport