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Cheap flights from Toronto Island Airport to Chicago from C$ 196

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 26/11. 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

Enter your travel dates to find the best prices.
Air Canada Logo
8:30 a.m. - 2:55 p.m.YTZ-ORD
7h 25m1 stop
Air Canada Logo
7:05 a.m. - 2:55 p.m.ORD-YTZ
6h 50m1 stop
C$ 318Air Canada
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Air Canada Logo
10:30 a.m. - 2:55 p.m.YTZ-ORD
5h 25m1 stop
Air Canada Logo
12:50 p.m. - 7:55 p.m.ORD-YTZ
6h 05m1 stop
C$ 343Air Canada
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Air Canada Logo
8:30 a.m. - 2:55 p.m.YTZ-ORD
7h 25m1 stop
Air Canada Logo
12:50 p.m. - 7:55 p.m.ORD-YTZ
6h 05m1 stop
C$ 344Air Canada
Find Deal
Wed, 5 Nov - Sat, 8 Nov
Air Canada Logo
10:30 a.m. - 2:55 p.m.YTZ-ORD
5h 25m1 stop
Air Canada Logo
7:05 a.m. - 6:13 p.m.ORD-YTZ
10h 08m2 stops
C$ 347Air Canada
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Air Canada Logo
8:30 a.m. - 2:55 p.m.YTZ-ORD
7h 25m1 stop
Air Canada Logo
7:05 a.m. - 2:55 p.m.ORD-YTZ
6h 50m1 stop
C$ 349Air Canada
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Air Canada Logo
8:30 a.m. - 2:55 p.m.YTZ-ORD
7h 25m1 stop
Air Canada Logo
7:05 a.m. - 2:55 p.m.ORD-YTZ
6h 50m1 stop
C$ 350Air Canada
Find Deal
Sat, 15 Nov - Tue, 18 Nov
Air Canada Logo
10:30 a.m. - 2:55 p.m.YTZ-ORD
5h 25m1 stop
Air Canada Logo
7:05 a.m. - 2:55 p.m.ORD-YTZ
6h 50m1 stop
C$ 353Air Canada
Find Deal
Wed, 26 Nov - Wed, 3 Dec
Air Canada Logo
3:30 p.m. - 8:00 p.m.YTZ-ORD
5h 30m1 stop
Air Canada Logo
12:50 p.m. - 7:55 p.m.ORD-YTZ
6h 05m1 stop
C$ 354Air Canada
Find Deal
Sat, 8 Nov - Fri, 14 Nov
Multiple Airlines Logo
7:45 a.m. - 1:03 a.m.YTZ-ORD
18h 18m3 stops
Multiple Airlines Logo
5:05 a.m. - 10:23 p.m.ORD-YTZ
16h 18m2 stops
C$ 438Multiple Airlines
Find Deal
Tue, 28 Oct - Wed, 29 Oct
Multiple Airlines Logo
7:40 p.m. - 12:45 p.m.YTZ-ORD
18h 05m1 stop
Multiple Airlines Logo
7:34 p.m. - 10:35 a.m.ORD-YTZ
14h 01m1 stop
C$ 447Multiple Airlines
Find Deal
Mon, 3 Nov - Wed, 19 Nov

Air Canada flights from Toronto Island Airport to Chicago O'Hare Intl Airport

Our best Air Canada deals on Toronto Island Airport to Chicago O'Hare Intl Airport flight tickets
Air Canada
26 Nov
YTZ8:30 a.m.Toronto Island
7h 25m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
3 Dec
ORD7:05 a.m.Chicago O'Hare Intl
6h 50m
1 stop
YTZ2:55 p.m.Toronto Island
C$ 318
Find similar
Air Canada
4 Dec
YTZ10:30 a.m.Toronto Island
5h 25m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
7 Dec
ORD12:50 p.m.Chicago O'Hare Intl
6h 05m
1 stop
YTZ7:55 p.m.Toronto Island
C$ 343
Find similar
Air Canada
5 Nov
YTZ8:30 a.m.Toronto Island
7h 25m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
8 Nov
ORD12:50 p.m.Chicago O'Hare Intl
6h 05m
1 stop
YTZ7:55 p.m.Toronto Island
C$ 344
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Toronto Island Airport to Chicago O'Hare Intl Airport 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 96,600 searches. Data last updated 13 October 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 26/11

8:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Wed 3/12

7:05 a.m.-2:55 p.m.

1 stop6h 50m

C$ 318

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 4/12

10:30 a.m.-2:55 p.m.

1 stop5h 25m

Chicago O'Hare Intl

Sun 7/12

12:50 p.m.-7:55 p.m.

1 stop6h 05m

C$ 343

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 5/11

8:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Sat 8/11

12:50 p.m.-7:55 p.m.

1 stop6h 05m

C$ 344

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 26/11

10:30 a.m.-2:55 p.m.

1 stop5h 25m

Chicago O'Hare Intl

Wed 3/12

7:05 a.m.-6:13 p.m.

2 stops10h 08m

C$ 347

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 26/11

8:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Wed 3/12

7:05 a.m.-2:55 p.m.

1 stop6h 50m

C$ 349

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 15/11

8:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Tue 18/11

7:05 a.m.-2:55 p.m.

1 stop6h 50m

C$ 350

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 26/11

10:30 a.m.-2:55 p.m.

1 stop5h 25m

Chicago O'Hare Intl

Wed 3/12

7:05 a.m.-2:55 p.m.

1 stop6h 50m

C$ 353

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 8/11

3:30 p.m.-8:00 p.m.

1 stop5h 30m

Chicago O'Hare Intl

Fri 14/11

12:50 p.m.-7:55 p.m.

1 stop6h 05m

C$ 354

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 28/10

7:45 a.m.-1:03 a.m.

3 stops18h 18m

Chicago O'Hare Intl

Wed 29/10

5:05 a.m.-10:23 p.m.

2 stops16h 18m

C$ 438

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 3/11

7:40 p.m.-12:45 p.m.

1 stop18h 05m

Chicago O'Hare Intl

Wed 19/11

7:34 p.m.-10:35 a.m.

1 stop14h 01m

C$ 447

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Toronto Island Airport to Chicago O'Hare Intl Airport

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 day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 725. 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 O'Hare Intl Airport for around C$ 1,155.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

In the evening is the cheapest time of day to fly from Toronto Island Airport to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 637. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 1,173 on average. Flights to Chicago O'Hare Intl Airport from Toronto Island Airport in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.

When to book flights from Toronto Island Airport to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Island Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (YTZ to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Island Airport to Chicago O'Hare Intl Airport

Direct flights

None
There are no direct flights from Toronto Island Airport to Chicago O'Hare Intl Airport. There are no popular flight routes from Toronto Island Airport to Chicago O'Hare Intl Airport.
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  • How far is Toronto Island to Chicago O'Hare Intl by plane?

    A flight from Toronto Island to Chicago O'Hare Intl will travel around 716.9 km. In terms of flight time, this usually takes a little over 4h 47m.

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

    Prices for flights from Toronto Island Airport to Chicago O'Hare Intl Airport are updated daily.

  • How many operators does momondo search for flights from Toronto Island Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Toronto Island Airport to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Toronto Island Airport to Chicago O'Hare Intl Airport?

Best airlines flying from Toronto Island Airport to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Toronto Island Airport to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 310Free CancellationRating
7.1
10,284 reviews
Search Air Canada flights

Travelling to a place near Chicago?

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Rockford

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Toronto to Chicago. momondo saves you time and could save you money on your trip.

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?

Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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