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Cheap flights from Toronto Island Airport to Chicago O'Hare Intl Airport from C$ 199

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 22/6. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — ORD
21 Feb — 28 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Toronto Island to O'Hare Intl

Enter your travel dates to find the best prices.

Cheapest flights from Toronto Island to O'Hare Intl
Explore the most affordable flight options available from Toronto Island to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 22 January 2026.

Mon 16/27:00 a.m.
YTZ
-
ORD
1 stop5h 06m
Air Canada
Fri 20/27:15 a.m.
ORD
-
YTZ
1 stop6h 10m
Air Canada
Deal found 19/1C$ 318
Thu 19/210:45 a.m.
YTZ
-
ORD
1 stop5h 10m
Air Canada
Mon 23/23:35 p.m.
ORD
-
YTZ
1 stop5h 00m
Air Canada
Deal found 20/1C$ 325
Thu 5/28:30 a.m.
YTZ
-
ORD
1 stop7h 25m
Air Canada
Sun 8/23:35 p.m.
ORD
-
YTZ
1 stop5h 00m
Air Canada
Deal found 21/1C$ 333
Tue 3/210:45 a.m.
YTZ
-
ORD
1 stop5h 10m
Air Canada
Thu 5/27:15 a.m.
ORD
-
YTZ
1 stop6h 10m
Air Canada
Deal found 19/1C$ 339
Fri 13/27:00 a.m.
YTZ
-
ORD
1 stop5h 06m
Air Canada
Sun 15/27:15 a.m.
ORD
-
YTZ
1 stop6h 10m
Air Canada
Deal found 20/1C$ 340
Sat 21/28:30 a.m.
YTZ
-
ORD
1 stop7h 25m
Air Canada
Tue 24/23:35 p.m.
ORD
-
YTZ
1 stop5h 00m
Air Canada
Deal found 18/1C$ 361
Fri 6/210:45 a.m.
YTZ
-
ORD
1 stop5h 10m
Air Canada
Mon 9/212:50 p.m.
ORD
-
YTZ
1 stop6h 05m
Air Canada
Deal found 21/1C$ 364

Find flight deals from Toronto Island to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 22 January 2026.

Round-trip from

C$ 318

One-way from

C$ 199

Popular in

January

Cheapest in

July

Average price

C$ 405

Good round-trip deal

C$ 1,211 or less
Air Canada
  • Air Canada
  • 16/2-20/2
  • 2 total stops
  • 11h 16m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 22/6
  • Nonstop
  • 1h 56m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Toronto Island to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto Island to O'Hare Intl 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, Cheapflights users made 629,999 searches. Data last updated 22 January 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

Toronto Island

Fly to

O'Hare Intl

Route

Depart

Return

Price

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 5/2

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

1 stop7h 25m

Chicago O'Hare Intl

Sun 8/2

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

1 stop5h 00m

C$ 333

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 24/2

7:00 a.m.-11:06 a.m.

1 stop5h 06m

Chicago O'Hare Intl

Fri 27/2

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

1 stop5h 00m

C$ 361

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 19/2

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

1 stop5h 10m

Chicago O'Hare Intl

Mon 23/2

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

1 stop5h 00m

C$ 361

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 21/2

12:30 p.m.-8:10 p.m.

2 stops8h 40m

Chicago O'Hare Intl

Tue 24/2

7:15 a.m.-2:25 p.m.

1 stop6h 10m

C$ 364

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 2/3

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

1 stop5h 10m

Chicago O'Hare Intl

Wed 4/3

7:15 a.m.-2:25 p.m.

1 stop6h 10m

C$ 420

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 29/4

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

1 stop7h 25m

Chicago O'Hare Intl

Mon 4/5

8:45 a.m.-3:52 p.m.

1 stop6h 07m

C$ 422

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 10/2

12:30 p.m.-6:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Thu 12/2

7:25 a.m.-3:13 p.m.

1 stop6h 48m

C$ 424

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 22/6

7:20 p.m.-8:16 p.m.

Nonstop1h 56m

C$ 199

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 3/2

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

1 stop5h 10m

C$ 200

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 13/2

7:00 a.m.-11:06 a.m.

1 stop5h 06m

C$ 200

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

Showing 1-10 of 16 results
1
2

Best time to book a flight from Toronto Island to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Toronto Island with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Toronto Island Airport to Chicago O'Hare Intl Airport

What’s the top layover airport for flights from Toronto Island Airport to Chicago O'Hare Intl Airport?

Share of one-stop round-trip flights from Toronto Island Airport to Chicago O'Hare Intl Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.

Ottawa (YOW) – chosen by Cheapflights users on 83% of one-stop itineraries from Toronto Island Airport to Chicago O'Hare Intl Airport on Cheapflights.

What’s the cheapest layover airport for flights from Toronto Island Airport to Chicago O'Hare Intl Airport?

Average round-trip fare for 1-stop flights from Toronto Island Airport to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 344.

What’s the fastest layover option from Toronto Island Airport to Chicago O'Hare Intl Airport?

Shortest average travel time for 1-stop one-way flights from Toronto Island Airport to Chicago O'Hare Intl Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Ottawa (YOW) have the shortest average one-way travel time for 1-stop routes: 4h 13m.

Which airport typically offers the quickest layover for flights from Toronto Island Airport to Chicago O'Hare Intl Airport?

Average layover duration for 1-stop one-way flights from Toronto Island Airport to Chicago O'Hare Intl Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 15m.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated 22 January 2026.
Read reviews from past customers who have flown Air Canada from Toronto Island Airport to Chicago O'Hare Intl Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
10,646 reviews
Check prices

Overall

7.1

Comfort

7.1

Crew

7.8

Entertainment

6.8

Food

6.3

Boarding

7.3

Reviews

1 / 20
2.0
Mediocre

Sugith,Jan 2026

YYZ - YSB

8 am flight cancelled at 2 am. Rebooked next day. Had to pay to rebook myself on Porter to leave same day.
Air Canada
7.1
Good
10,646 reviews
Air Canada
7.1
Good
10,646 reviews
Check prices

Overall

7.1

Comfort

7.1

Crew

7.8

Entertainment

6.8

Food

6.3

Boarding

7.3

Reviews

1 / 20
2.0
Mediocre

Sugith,Jan 2026

YYZ - YSB

8 am flight cancelled at 2 am. Rebooked next day. Had to pay to rebook myself on Porter to leave same day.

Related info for your journey

Find useful and relevant information for your journey from Toronto Island to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Toronto Island Airport to Chicago O'Hare Intl Airport?

    For as low as C$ 333, Air Canada can have you in Chicago O'Hare Intl Airport from Toronto Island Airport in 7h 25m. The distance from Toronto Island Airport to Chicago O'Hare Intl Airport is about 716 km.

  • What is the cheapest airline to fly from Toronto Island Airport to Chicago O'Hare Intl Airport round-trip?

    Currently priced at C$ 306, Air Canada will fly you from Toronto Island Airport to Chicago O'Hare Intl Airport and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip.

  • What are the cheapest flights from Toronto Island Airport to Chicago O'Hare Intl Airport?

    The cheapest flight price from Toronto Island Airport to Chicago O'Hare Intl Airport is C$ 458. On average you can expect to pay C$ 1,285. The most popular route, (Toronto Island - Chicago O'Hare Intl), can usually be booked for C$ 364.

  • Can I find deals for flights from Toronto Island to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Toronto Island to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto Island to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto Island to O'Hare Intl.

  • Can I find deals for business class flights from Toronto Island to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Toronto Island to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Travelling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Evanston
Des Plaines
Skokie
Downers Grove
Elk Grove Village
Racine
Naperville
Bolingbrook
Romeoville

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Toronto Island to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Hamilton to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights

Top airline flying from Toronto Island to O'Hare Intl

Discover the top airline that operate flights from Toronto Island to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 22 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 306AverageC$ 443FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Toronto Island to O'Hare Intl?

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Why should you use Cheapflights to find cheap flight tickets from Toronto Island to O'Hare Intl?

Cheapflights helps you find that perfect flight to O'Hare Intl from Toronto Island by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Toronto Island to O'Hare Intl with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Toronto Island to O'Hare Intl, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Toronto Island to O'Hare Intl become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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