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Cheap flights from Toronto Island Airport to Chicago from C$ 190

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 15/9. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
12:15 p.m. - 1:21 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 06mdirect
Air Canada Logo
7:25 a.m. - 10:07 a.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 279Air Canada
Thu, 10 Sep - Sun, 13 Sep
Air Canada Logo
12:15 p.m. - 1:21 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 06mdirect
Air Canada Logo
7:25 a.m. - 10:07 a.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 280Air Canada
Mon, 28 Sep - Wed, 30 Sep
Air Canada Logo
7:45 p.m. - 8:51 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 06mdirect
Air Canada Logo
2:00 p.m. - 4:42 p.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 280Air Canada
Fri, 4 Sep - Fri, 11 Sep
Air Canada Logo
12:15 p.m. - 1:21 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 06mdirect
Air Canada Logo
2:00 p.m. - 4:42 p.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 280Air Canada
Fri, 18 Sep - Sun, 20 Sep
Air Canada Logo
10:45 a.m. - 2:52 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
5h 07m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
2:00 p.m. - 4:42 p.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 280Air Canada
Tue, 29 Sep - Wed, 30 Sep
Air Canada Logo
7:35 p.m. - 8:41 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 06mdirect
Air Canada Logo
7:25 a.m. - 10:07 a.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 280Air Canada
Tue, 1 Sep - Sat, 12 Sep
Air Canada Logo
12:15 p.m. - 1:21 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 06mdirect
Air Canada Logo
2:00 p.m. - 4:42 p.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 280Air Canada
Tue, 8 Sep - Fri, 11 Sep
Air Canada Logo
7:35 p.m. - 8:41 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 06mdirect
Air Canada Logo
7:25 a.m. - 10:07 a.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 42mdirect
C$ 280Air Canada
Wed, 16 Sep - Sun, 20 Sep
Porter Airlines Logo
4:35 p.m. - 5:30 p.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
1h 55mdirect
Porter Airlines Logo
6:10 p.m. - 8:50 p.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 40mdirect
C$ 284Porter Airlines
Fri, 6 Nov - Mon, 9 Nov
Porter Airlines Logo
10:05 a.m. - 11:00 a.m.YTZ  Toronto Island-ORD Chicago O'Hare Intl
1h 55mdirect
Porter Airlines Logo
7:00 a.m. - 9:40 a.m.ORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 40mdirect
C$ 304Porter Airlines
Tue, 8 Sep - Mon, 14 Sep

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Porter Airlines flights from Toronto Island Airport to Chicago O'Hare Intl Airport

Our best Porter Airlines deals on Toronto Island Airport to Chicago O'Hare Intl Airport flight tickets
Porter Airlines
6 Nov
YTZ4:35 p.m.Toronto Island
1h 55m
ORD5:30 p.m.Chicago O'Hare Intl
9 Nov
ORD6:10 p.m.Chicago O'Hare Intl
1h 40m
YTZ8:50 p.m.Toronto Island
C$ 284
Porter Airlines
8 Sep
YTZ10:05 a.m.Toronto Island
1h 55m
ORD11:00 a.m.Chicago O'Hare Intl
14 Sep
ORD7:00 a.m.Chicago O'Hare Intl
1h 40m
YTZ9:40 a.m.Toronto Island
C$ 304

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
10 Sep
YTZ12:15 p.m.Toronto Island
2h 06m
ORD1:21 p.m.Chicago O'Hare Intl
13 Sep
ORD7:25 a.m.Chicago O'Hare Intl
1h 42m
YTZ10:07 a.m.Toronto Island
C$ 279
Air Canada
8 Sep
YTZ12:15 p.m.Toronto Island
2h 06m
ORD1:21 p.m.Chicago O'Hare Intl
15 Sep
ORD7:25 a.m.Chicago O'Hare Intl
1h 42m
YTZ10:07 a.m.Toronto Island
C$ 280
Air Canada
12 Sep
YTZ7:35 p.m.Toronto Island
2h 06m
ORD8:41 p.m.Chicago O'Hare Intl
18 Sep
ORD7:25 a.m.Chicago O'Hare Intl
1h 42m
YTZ10:07 a.m.Toronto Island
C$ 281

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 9 August 2026.
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

Cheapest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 10/9

12:15 p.m.-1:21 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 13/9

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

C$ 279

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Mon 28/9

12:15 p.m.-1:21 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 30/9

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 4/9

7:45 p.m.-8:51 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Fri 11/9

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 18/9

12:15 p.m.-1:21 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 20/9

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 29/9

10:45 a.m.-2:52 p.m.

1 stop5h 07m

Chicago O'Hare Intl

Wed 30/9

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 1/9

7:35 p.m.-8:41 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sat 12/9

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 8/9

12:15 p.m.-1:21 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Fri 11/9

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 16/9

7:35 p.m.-8:41 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 20/9

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

C$ 280
Quickest round-trip

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 6/11

4:35 p.m.-5:30 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Mon 9/11

6:10 p.m.-8:50 p.m.

Nonstop1h 40m

C$ 284

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 8/9

10:05 a.m.-11:00 a.m.

Nonstop1h 55m

Chicago O'Hare Intl

Mon 14/9

7:00 a.m.-9:40 a.m.

Nonstop1h 40m

C$ 304

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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$ 688. 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$ 1,011.

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$ 708. 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$ 1,084 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.

What is the cheapest Toronto Island to Chicago O'Hare Intl flight route?

Fly from Toronto Island to Chicago O'Hare Intl for the best Toronto Island - Chicago O'Hare Intl flight prices

What cabin class options are available on Toronto Island Airport to Chicago O'Hare Intl Airport flights?

There are 3 cabin classes available to choose from on Toronto Island Airport to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Toronto Island Airport to Chicago O'Hare Intl Airport.

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$ 220

Fastest flight time

1h 55m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Toronto Island Airport in the past 72 hours is C$ 220. The best round-trip flight deal from Toronto Island Airport to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is C$ 334.
The fastest flight from Toronto Island Airport to Chicago O'Hare Intl Airport takes 1h 55m
Direct flights go from Toronto Island Airport to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from Toronto Island Airport to Chicago O'Hare Intl Airport

  • 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 1h 55m.

  • 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$ 135Free CancellationRating
7.1
11,455 reviews
Search Air Canada flights

  • Air Canada Flights From Toronto Island Airport to Chicago O'Hare Intl Airport

    Across 5 Air Canada flights from Toronto Island Airport to Chicago O'Hare Intl Airport this week, the average price was C$ 504, with the best Air Canada deals starting from C$ 135 round-trip. 11,455 users have rated Air Canada on momondo, with an average score of 7.1/10.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Schaumburg
Crystal Lake
Glenview
Waukegan
Rosemont
Des Plaines
Merrillville
Kenosha
Northbrook
Skokie
Tinley Park
Evanston
Downers Grove
Great Lakes
Hammond
Naperville
Harvey
Munster
Hoffman Estates
Elmhurst

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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