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Cheap flights from Toronto Island Airport to Chicago from C$ 164

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 12/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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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.
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 281Porter Airlines
Find Deal
Wed, 15 Jan - Fri, 17 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 286Porter Airlines
Find Deal
Fri, 24 Jan - Sun, 26 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 287Porter Airlines
Find Deal
Wed, 15 Jan - Sun, 19 Jan
12:25 p.m. - 6:50 p.m.YTZ-ORD
7h 25m1 stop
11:35 a.m. - 5:50 p.m.ORD-YTZ
5h 15m1 stop
C$ 321Air Canada
Find Deal
Sat, 18 Jan - Sun, 2 Feb
3:25 p.m. - 7:55 p.m.YTZ-ORD
5h 30m1 stop
1:55 p.m. - 8:43 p.m.ORD-YTZ
5h 48m1 stop
C$ 326Air Canada
Find Deal
Tue, 14 Jan - Wed, 15 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 334Air Transat
Find Deal
Thu, 9 Jan - Sun, 12 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 336Air Transat
Find Deal
Thu, 9 Jan - Sun, 12 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
5:30 a.m. - 4:48 p.m.MDW-YTZ
10h 18m2 stops
C$ 357
Find Deal
Sun, 12 Jan - Fri, 17 Jan
6:45 a.m. - 11:06 a.m.YTZ-ORD
5h 21m1 stop
5:08 a.m. - 4:48 p.m.ORD-YTZ
10h 40m2 stops
C$ 360
Find Deal
Wed, 12 Feb - Mon, 24 Feb
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 1,014APG Airlines
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Tue, 13 May - Fri, 16 May
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 164Porter Airlines
Find Deal
Sun, 12 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 169Porter Airlines
Find Deal
Sat, 18 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 170Porter Airlines
Find Deal
Fri, 31 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 171Porter Airlines
Find Deal
Sat, 25 Jan
3:25 p.m. - 7:55 p.m.YTZ-ORD
5h 30m1 stop
C$ 191Air Canada
Find Deal
Wed, 15 Jan
10:25 a.m. - 2:45 p.m.YTZ-ORD
5h 20m1 stop
C$ 201Air Canada
Find Deal
Wed, 12 Feb
7:00 a.m. - 11:32 p.m.YTZ-ORD
17h 32m2 stops
C$ 213
Find Deal
Wed, 29 Jan
9:00 a.m. - 7:19 p.m.YTZ-ORD
11h 19m1 stop
C$ 220
Find Deal
Wed, 8 Jan
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
C$ 277Air Transat
Find Deal
Sat, 4 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 357Air Transat
Find Deal
Wed, 25 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 554Porter Airlines
Find Deal
Sat, 21 Dec - Tue, 31 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 557Porter Airlines
Find Deal
Sun, 22 Dec - Thu, 2 Jan
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 581Porter Airlines
Find Deal
Thu, 19 Dec - Fri, 3 Jan
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 586Porter Airlines
Find Deal
Thu, 19 Dec - Sat, 4 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 593Porter Airlines
Find Deal
Fri, 20 Dec - Fri, 27 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 597Porter Airlines
Find Deal
Sat, 21 Dec - Sat, 28 Dec
1:10 p.m. - 12:47 a.m.YTZ-ORD
12h 37m2 stops
1:24 p.m. - 9:20 p.m.ORD-YTZ
6h 56m1 stop
C$ 671
Find Deal
Thu, 19 Dec - Sun, 5 Jan
10:25 a.m. - 2:45 p.m.YTZ-ORD
5h 20m1 stop
7:20 a.m. - 2:50 p.m.ORD-YTZ
6h 30m1 stop
C$ 871Air Canada
Find Deal
Mon, 23 Dec - Wed, 25 Dec
3:25 p.m. - 7:55 p.m.YTZ-ORD
5h 30m1 stop
7:20 a.m. - 2:50 p.m.ORD-YTZ
6h 30m1 stop
C$ 984Air Canada
Find Deal
Mon, 23 Dec - Wed, 25 Dec
3:25 p.m. - 7:55 p.m.YTZ-ORD
5h 30m1 stop
7:20 a.m. - 2:50 p.m.ORD-YTZ
6h 30m1 stop
C$ 990Air Canada
Find Deal
Fri, 20 Dec - Mon, 23 Dec
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 281Porter Airlines
Find Deal
Wed, 15 Jan - Fri, 17 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 286Porter Airlines
Find Deal
Fri, 24 Jan - Sun, 26 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 287Porter Airlines
Find Deal
Wed, 15 Jan - Sun, 19 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 289Porter Airlines
Find Deal
Wed, 15 Jan - Sun, 19 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 290Porter Airlines
Find Deal
Sun, 19 Jan - Thu, 30 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 291Porter Airlines
Find Deal
Thu, 9 Jan - Sun, 12 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 334Air Transat
Find Deal
Thu, 9 Jan - Sun, 12 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 336Air Transat
Find Deal
Thu, 9 Jan - Sun, 12 Jan
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 354Air Transat
Find Deal
Thu, 9 Jan - Sun, 12 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
C$ 384
Find Deal
Mon, 6 Jan - Fri, 7 Feb

Air Canada flights from Toronto Island Airport to Chicago

Our best Air Canada deals on Toronto Island Airport to Chicago flight tickets
Air Canada
18 Jan
YTZ12:25 p.m.Toronto Island
7h 25m
1 stop
ORD6:50 p.m.Chicago O'Hare Intl
2 Feb
ORD11:35 a.m.Chicago O'Hare Intl
5h 15m
1 stop
YTZ5:50 p.m.Toronto Island
Air Canada
14 Jan
YTZ3:25 p.m.Toronto Island
5h 30m
1 stop
ORD7:55 p.m.Chicago O'Hare Intl
15 Jan
ORD1:55 p.m.Chicago O'Hare Intl
5h 48m
1 stop
YTZ8:43 p.m.Toronto Island
Air Canada
1 Feb
YTZ8:25 a.m.Toronto Island
7h 20m
1 stop
ORD2:45 p.m.Chicago O'Hare Intl
8 Feb
ORD3:35 p.m.Chicago O'Hare Intl
5h 15m
1 stop
YTZ9:50 p.m.Toronto Island

Air Transat flights from Toronto Island Airport to Chicago

Our best Air Transat deals on Toronto Island Airport to Chicago flight tickets
Air Transat
9 Jan
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
12 Jan
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Air Transat
9 Jan
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
12 Jan
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto Island
Air Transat
9 Jan
YTZ11:20 a.m.Toronto Island
1h 50m
MDW12:10 p.m.Chicago Midway
12 Jan
MDW1:05 p.m.Chicago Midway
1h 42m
YTZ3:47 p.m.Toronto 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 February is another great option to travel to Chicago, with average flight prices from Toronto Island Airport averaging around C$ 347.

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 Saturday when prices can be found for as low as C$ 384. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 411. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the afternoon is the cheapest time of day to fly from Toronto Island Airport to Chicago when you can find flight prices for as low as C$ 379. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 433 per ticket.

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 1 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 16% 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

C$ 164

Fastest flight time

1h 45m

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 C$ 164. The best round-trip flight deal from Toronto Island Airport to Chicago found on momondo in the last 72 hours is C$ 281.
The fastest flight from Toronto Island Airport to Chicago takes 1h 45m
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 698.8 km. A reasonable flight in good conditions will take 1h 45m.

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

    Prices for flights from Toronto Island Airport to Chicago were last updated today.

  • 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 that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 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 C$ 286Free CancellationRating
7.9
283 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 350Free CancellationRating
7.0
8,382 reviews
Search Air Canada flights
  • Porter Airlines Flights From Toronto Island Airport to Chicago

    The lowest priced Porter Airlines flight from Toronto Island Airport to Chicago from the last 72 hours was C$ 200. Generally, Porter Airlines has 12 flights on this route every week with an average price of C$ 270. Porter Airlines is rated 7.9/10 by our users.


Why use momondo?

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

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 Chicago from Toronto.

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

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.

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

Price alerts on flights to Chicago 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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago