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Cheap flights from Toronto Island Airport to Chicago from C$ 174

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 11/12. 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
10:30 a.m. - 2:55 p.m.YTZ-ORD
5h 25m1 stop
Air Canada Logo
3:35 p.m. - 9:35 p.m.ORD-YTZ
5h 00m1 stop
C$ 286Air Canada
Find Deal
Fri, 23 Jan - Mon, 26 Jan
Air Canada Logo
3:30 p.m. - 8:10 p.m.YTZ-ORD
5h 40m1 stop
Air Canada Logo
3:35 p.m. - 9:35 p.m.ORD-YTZ
5h 00m1 stop
C$ 307Air Canada
Find Deal
Tue, 13 Jan - Tue, 20 Jan
Air Canada Logo
3:30 p.m. - 8:10 p.m.YTZ-ORD
5h 40m1 stop
Air Canada Logo
7:15 a.m. - 2:55 p.m.ORD-YTZ
6h 40m1 stop
C$ 310Air Canada
Find Deal
Mon, 12 Jan - Mon, 19 Jan
Air Canada Logo
10:30 a.m. - 2:55 p.m.YTZ-ORD
5h 25m1 stop
Air Canada Logo
7:15 a.m. - 2:55 p.m.ORD-YTZ
6h 40m1 stop
C$ 311Air Canada
Find Deal
Sat, 17 Jan - Sat, 31 Jan
Air Canada Logo
10:45 a.m. - 2:55 p.m.YTZ-ORD
5h 10m1 stop
Air Canada Logo
3:35 p.m. - 9:35 p.m.ORD-YTZ
5h 00m1 stop
C$ 312Air Canada
Find Deal
Sat, 14 Feb - Mon, 16 Feb
Air Canada Logo
3:30 p.m. - 8:10 p.m.YTZ-ORD
5h 40m1 stop
Air Canada Logo
12:50 p.m. - 7:55 p.m.ORD-YTZ
6h 05m1 stop
C$ 314Air Canada
Find Deal
Mon, 12 Jan - Mon, 19 Jan
Air Canada Logo
6:45 p.m. - 11:06 a.m.YTZ-ORD
17h 21m2 stops
Air Canada Logo
3:35 p.m. - 9:35 p.m.ORD-YTZ
5h 00m1 stop
C$ 340Air Canada
Find Deal
Mon, 12 Jan - Mon, 19 Jan
Air Canada Logo
6:45 p.m. - 11:06 a.m.YTZ-ORD
17h 21m2 stops
Air Canada Logo
3:35 p.m. - 9:35 p.m.ORD-YTZ
5h 00m1 stop
C$ 350Air Canada
Find Deal
Mon, 12 Jan - Mon, 19 Jan
Air Canada Logo
8:30 a.m. - 2:55 p.m.YTZ-ORD
7h 25m1 stop
Air Canada Logo
10:35 a.m. - 4:55 p.m.ORD-YTZ
5h 20m1 stop
C$ 364Air Canada
Find Deal
Fri, 16 Jan - Fri, 23 Jan
Multiple Airlines Logo
2:05 p.m. - 2:39 p.m.YTZ-ORD
25h 34m2 stops
Multiple Airlines Logo
4:38 p.m. - 11:40 a.m.ORD-YTZ
18h 02m1 stop
C$ 366Multiple Airlines
Find Deal
Fri, 16 Jan - Fri, 23 Jan

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
23 Jan
YTZ10:30 a.m.Toronto Island
5h 25m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
26 Jan
ORD3:35 p.m.Chicago O'Hare Intl
5h 00m
1 stop
YTZ9:35 p.m.Toronto Island
C$ 286
Find similar
Air Canada
12 Jan
YTZ3:30 p.m.Toronto Island
5h 40m
1 stop
ORD8:10 p.m.Chicago O'Hare Intl
19 Jan
ORD7:15 a.m.Chicago O'Hare Intl
6h 40m
1 stop
YTZ2:55 p.m.Toronto Island
C$ 310
Find similar
Air Canada
17 Jan
YTZ10:30 a.m.Toronto Island
5h 25m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
31 Jan
ORD7:15 a.m.Chicago O'Hare Intl
6h 40m
1 stop
YTZ2:55 p.m.Toronto Island
C$ 311
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 29 November 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

Fri 23/1

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

1 stop5h 25m

Chicago O'Hare Intl

Mon 26/1

3:35 p.m.-9:35 p.m.

1 stop5h 00m

C$ 286

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 13/1

3:30 p.m.-8:10 p.m.

1 stop5h 40m

Chicago O'Hare Intl

Tue 20/1

3:35 p.m.-9:35 p.m.

1 stop5h 00m

C$ 307

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 12/1

3:30 p.m.-8:10 p.m.

1 stop5h 40m

Chicago O'Hare Intl

Mon 19/1

7:15 a.m.-2:55 p.m.

1 stop6h 40m

C$ 310

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 17/1

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

1 stop5h 25m

Chicago O'Hare Intl

Sat 31/1

7:15 a.m.-2:55 p.m.

1 stop6h 40m

C$ 311

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 14/2

10:45 a.m.-2:55 p.m.

1 stop5h 10m

Chicago O'Hare Intl

Mon 16/2

3:35 p.m.-9:35 p.m.

1 stop5h 00m

C$ 312

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 12/1

3:30 p.m.-8:10 p.m.

1 stop5h 40m

Chicago O'Hare Intl

Mon 19/1

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

1 stop6h 05m

C$ 314

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 12/1

6:45 p.m.-11:06 a.m.

2 stops17h 21m

Chicago O'Hare Intl

Mon 19/1

3:35 p.m.-9:35 p.m.

1 stop5h 00m

C$ 340

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 12/1

6:45 p.m.-11:06 a.m.

2 stops17h 21m

Chicago O'Hare Intl

Mon 19/1

3:35 p.m.-9:35 p.m.

1 stop5h 00m

C$ 350

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 16/1

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 23/1

10:35 a.m.-4:55 p.m.

1 stop5h 20m

C$ 364

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 16/1

2:05 p.m.-2:39 p.m.

2 stops25h 34m

Chicago O'Hare Intl

Fri 23/1

4:38 p.m.-11:40 a.m.

1 stop18h 02m

C$ 366

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$ 685. 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$ 1,102.

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$ 635. 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 at noon when prices are C$ 1,114 on average. Flights to Chicago O'Hare Intl Airport from Toronto Island Airport at noon 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

Best price found

C$ 1,144

Fastest flight time

3h 58m

Direct flights

None
The best flight deal from Toronto Island Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 1,144
The fastest flight from Toronto Island Airport to Chicago O'Hare Intl Airport takes 3h 58m
There are no direct flights from Toronto Island Airport to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Toronto Island Airport - Chicago O'Hare Intl Airport.
Search flight deals

  • 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 5h 06m.

  • 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 plane model from Toronto Island Airport to Chicago O'Hare Intl Airport?

  • 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
10,484 reviews
Search Air Canada flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Northbrook
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Munster
Hammond
Harvey
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Elmhurst
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Kenosha
Skokie

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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