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Cheap flights from Toronto Island Airport to Chicago from $108

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 2/20. 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

These are some of the best round-trip flight deals from Toronto Island Airport to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Toronto Island Airport to Chicago.

Cheap last minute flights

Planning a quick getaway from Toronto Island Airport to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Toronto Island Airport to Chicago

Find recent round-trip train or bus tickets from Toronto Island Airport to Chicago.

All round-trip flight deals from Toronto Island Airport to Chicago

The cheapest plane tickets from Toronto Island Airport to Chicago found on KAYAK recently.
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$180Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$181Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$182Porter Airlines
Find Deal
Wed, Feb 12 - Sat, Feb 22
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$204Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$206Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
8:50 am - 12:59 pmYTZ-ORD
5h 09m1 stop
1:58 pm - 8:43 pmORD-YTZ
5h 45m1 stop
$248Air Canada
Find Deal
Fri, Feb 14 - Mon, Feb 17
8:50 am - 12:59 pmYTZ-ORD
5h 09m1 stop
3:35 pm - 9:50 pmORD-YTZ
5h 15m1 stop
$250Air Canada
Find Deal
Fri, Feb 14 - Sun, Feb 23
11:20 am - 6:23 pmYTZ-MDW
8h 03m1 stop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
Wed, Feb 12 - Thu, Feb 13
2:00 pm - 10:40 amYTZ-ORD
21h 40m2 stops
7:10 am - 10:23 pmORD-YTZ
14h 13m2 stops
Tue, Feb 18 - Tue, Feb 25
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$296APG Airlines
Find Deal
Thu, Mar 6 - Thu, Mar 13
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$108Porter Airlines
Find Deal
Thu, Feb 20
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$111Porter Airlines
Find Deal
Wed, Feb 19
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$112Porter Airlines
Find Deal
Tue, Feb 18
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$113Porter Airlines
Find Deal
Wed, Feb 12
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$131Air Transat
Find Deal
Fri, Apr 11
6:45 am - 11:05 amYTZ-ORD
5h 20m1 stop
Wed, Feb 12
7:45 pm - 11:05 amYTZ-ORD
16h 20m1 stop
Tue, Feb 11
8:50 am - 12:59 pmYTZ-ORD
5h 09m1 stop
$145Air Canada
Find Deal
Fri, Feb 14
8:50 am - 12:59 pmYTZ-ORD
5h 09m1 stop
$147Air Canada
Find Deal
Wed, Feb 26
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$159Air Transat
Find Deal
Fri, Feb 7
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$302Porter Airlines
Find Deal
Fri, Jan 24 - Mon, Feb 10
9:50 am - 9:39 amYTZ-ORD
24h 49m2 stops
5:35 am - 6:53 pmORD-YTZ
12h 18m2 stops
Sun, Jan 26 - Tue, Jan 28
9:50 am - 9:39 amYTZ-ORD
24h 49m2 stops
5:35 am - 6:53 pmORD-YTZ
12h 18m2 stops
Sun, Jan 26 - Tue, Jan 28
10:00 am - 9:39 amYTZ-ORD
24h 39m3 stops
5:35 am - 8:05 pmORD-YTZ
13h 30m2 stops
Sat, Jan 25 - Mon, Jan 27
3:30 pm - 11:20 amYTZ-ORD
20h 50m3 stops
5:15 am - 1:55 pmORD-YTZ
7h 40m1 stop
Thu, Jan 23 - Thu, Feb 20
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$383Porter Airlines
Find Deal
Fri, Jan 24 - Mon, Jan 27
12:25 pm - 6:50 pmYTZ-ORD
7h 25m1 stop
7:20 am - 2:50 pmORD-YTZ
6h 30m1 stop
$384Air Canada
Find Deal
Fri, Jan 24 - Thu, Feb 20
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$391Porter Airlines
Find Deal
Fri, Jan 24 - Mon, Jan 27
12:25 pm - 6:50 pmYTZ-ORD
7h 25m1 stop
2:01 pm - 7:50 pmORD-YTZ
4h 49m1 stop
$419Air Canada
Find Deal
Fri, Jan 24 - Mon, Feb 10
12:25 pm - 6:50 pmYTZ-ORD
7h 25m1 stop
1:55 pm - 8:43 pmORD-YTZ
5h 48m1 stop
$469Air Canada
Find Deal
Fri, Jan 24 - Sat, Jan 25
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$180Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$181Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$182Porter Airlines
Find Deal
Wed, Feb 12 - Sat, Feb 22
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$183Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$186Porter Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$187Porter Airlines
Find Deal
Tue, Feb 18 - Tue, Feb 25
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$204Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$206Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$207Air Transat
Find Deal
Thu, Feb 13 - Sun, Feb 16
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$296APG Airlines
Find Deal
Thu, Mar 6 - Thu, Mar 13

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada deals on Toronto Island Airport to Chicago flight tickets
Air Canada
Feb 14
YTZ8:50 amToronto Island
5h 09m
1 stop
ORD12:59 pmChicago O'Hare Intl
Feb 17
ORD1:58 pmChicago O'Hare Intl
5h 45m
1 stop
YTZ8:43 pmToronto Island
Air Canada
Feb 14
YTZ8:50 amToronto Island
5h 09m
1 stop
ORD12:59 pmChicago O'Hare Intl
Feb 23
ORD3:35 pmChicago O'Hare Intl
5h 15m
1 stop
YTZ9:50 pmToronto Island
Air Canada
Apr 25
YTZ7:25 amToronto Island
5h 07m
1 stop
ORD11:32 amChicago O'Hare Intl
Apr 29
ORD1:56 pmChicago O'Hare Intl
5h 41m
1 stop
YTZ8:37 pmToronto Island

Porter Airlines flights from Toronto Island Airport to Chicago

Our best Porter Airlines deals on Toronto Island Airport to Chicago flight tickets
Porter Airlines
Feb 13
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 16
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island
Porter Airlines
Feb 13
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 16
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island
Porter Airlines
Feb 12
YTZ11:20 amToronto Island
1h 50m
MDW12:10 pmChicago Midway
Feb 22
MDW1:05 pmChicago Midway
1h 42m
YTZ3:47 pmToronto Island

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 December is, on average, the cheapest month to fly to Chicago from Toronto Island Airport, with most prices found around $230. If you’re not able to fly to Chicago in December, then May is your next best option. Flight prices from Toronto Island Airport to Chicago during May average around $243.

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 Wednesday when prices can be found for as low as $258. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Island Airport to Chicago for around $292.

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 $269. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $325.

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.

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

$108

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Toronto Island Airport in the past 72 hours is $108. The best round-trip flight deal from Toronto Island Airport to Chicago found on momondo in the last 72 hours is $180.
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 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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 50m.

  • 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 $209Free CancellationRating
7.9
277 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 $209 round-trip. Over the 6 Porter Airlines flights for this route in a normal week, average airfare is usually $260 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
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
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.


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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