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Cheap flights from Toronto Island Airport to Chicago from $133

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 12/14. 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 to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$255Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$261Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:25 am - 2:45 pmYTZ-ORD
5h 20m1 stop
2:01 pm - 7:50 pmORD-YTZ
4h 49m1 stop
$261Air Canada
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:25 am - 2:45 pmYTZ-ORD
5h 20m1 stop
11:35 am - 5:50 pmORD-YTZ
5h 15m1 stop
$264Air Canada
Find Deal
Thu, Dec 12 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
Wed, Dec 18 - Sun, Jan 5
3:00 pm - 12:34 amYTZ-ORD
10h 34m1 stop
6:37 pm - 8:30 amORD-YTZ
12h 53m1 stop
Mon, Dec 9 - Wed, Dec 11
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$133Porter Airlines
Find Deal
Sat, Dec 14
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$136Porter Airlines
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Sat, Dec 14
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$138Porter Airlines
Find Deal
Thu, Dec 12
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
$141Porter Airlines
Find Deal
Mon, Dec 16
8:25 am - 2:45 pmYTZ-ORD
7h 20m1 stop
$147Air Canada
Find Deal
Sat, Dec 14
8:25 am - 2:45 pmYTZ-ORD
7h 20m1 stop
$152Air Canada
Find Deal
Wed, Feb 12
4:30 pm - 12:34 amYTZ-ORD
9h 04m1 stop
Wed, Dec 11
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$170Air Transat
Find Deal
Mon, Jan 6
4:10 pm - 5:30 amYTZ-ORD
14h 20m2 stops
Wed, Jan 29
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$203Air Transat
Find Deal
Sat, Dec 21
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$375Porter Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 9
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$379Air Transat
Find Deal
Tue, Nov 26 - Thu, Jan 16
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$400Porter Airlines
Find Deal
Tue, Nov 26 - Fri, Dec 6
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$412Air Transat
Find Deal
Tue, Nov 26 - Wed, Dec 4
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$418Porter Airlines
Find Deal
Tue, Nov 26 - Thu, Nov 28
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
$438Porter Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
Mon, Nov 25 - Sat, Nov 30
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
Mon, Nov 25 - Fri, Nov 29
8:25 am - 2:45 pmYTZ-ORD
7h 20m1 stop
2:00 pm - 8:43 pmORD-YTZ
5h 43m1 stop
$594Air Canada
Find Deal
Sun, Nov 24 - Thu, Nov 28
8:25 am - 2:45 pmYTZ-ORD
7h 20m1 stop
2:00 pm - 8:43 pmORD-YTZ
5h 43m1 stop
$601Air Canada
Find Deal
Sun, Nov 24 - Tue, Dec 3
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$237Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$239Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$255Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$262Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$271Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
Wed, Dec 18 - Sun, Jan 5

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada deals on Toronto Island Airport to Chicago flight tickets
Air Canada
Dec 12
YTZ10:25 amToronto Island
5h 20m
1 stop
ORD2:45 pmChicago O'Hare Intl
Dec 15
ORD2:01 pmChicago O'Hare Intl
4h 49m
1 stop
YTZ7:50 pmToronto Island
Air Canada
Dec 12
YTZ10:25 amToronto Island
5h 20m
1 stop
ORD2:45 pmChicago O'Hare Intl
Dec 17
ORD11:35 amChicago O'Hare Intl
5h 15m
1 stop
YTZ5:50 pmToronto Island
Air Canada
Jan 13
YTZ3:25 pmToronto Island
5h 30m
1 stop
ORD7:55 pmChicago O'Hare Intl
Jan 17
ORD11:35 amChicago O'Hare Intl
5h 15m
1 stop
YTZ5:50 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
Dec 12
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 15
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Dec 13
YTZ10:20 amToronto Island
1h 50m
MDW11:10 amChicago Midway
Dec 17
MDW5:35 pmChicago Midway
1h 42m
YTZ8:17 pmToronto Island
Porter Airlines
Dec 12
YTZ3:50 pmToronto Island
1h 50m
MDW4:40 pmChicago Midway
Dec 16
MDW12:05 pmChicago Midway
1h 42m
YTZ2:47 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 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 April is, on average, the cheapest month to fly to Chicago from Toronto Island Airport, with most prices found around $239. If you’re not able to fly to Chicago in April, then February is your next best option. Flight prices from Toronto Island Airport to Chicago during February 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 $254. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, 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 $265. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $296.

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

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Toronto Island Airport is 34 days out, which is when prices tend to be around $265. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $219.

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

There are 3 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 8% 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

$133

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 $133. The best round-trip flight deal from Toronto Island Airport to Chicago found on momondo in the last 72 hours is $219.
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
Air CanadaPriceFrom $157Free CancellationRating
7.0
8,246 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $205Free CancellationRating
7.8
288 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 $205 round-trip. Over the 10 Porter Airlines flights for this route in a normal week, average airfare is usually $254 round-trip - but some users have found much cheaper deals with momondo.


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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago