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$106+ Cheap flights from Ontario to Chicago (CHI)

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Ontario to Chicago

Cheapest flights from Ontario to Chicago
Explore the most affordable flight options available from Ontario to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This SmartFares deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:00 amYYZ - ORD
1 stop5h 18mAir Canada
Mon 11/178:15 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 10/29$181
This Air Canada deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amYYZ - ORD
1 stop5h 18mAir Canada
Thu 2/122:00 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 10/29$183
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:58 amYYZ - ORD
1 stop9h 23mAmerican Airlines
Thu 2/127:19 amORD - YYZ
1 stop4h 43mAmerican Airlines
Deal found 10/29$184
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/1211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$185
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/249:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$187
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$188
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 12/148:10 amORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 10/29$189
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Thu 11/207:35 amORD - YYZ
1 stop4h 27mAmerican Airlines
Deal found 10/29$190
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/174:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$190
This American Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:44 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Tue 12/96:22 amORD - YYZ
1 stop5h 38mAmerican Airlines
Deal found 10/28$193
This Kiwi.com deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 12/1411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$193
This American Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 12/75:00 amORD - YYZ
1 stop5h 02mAmerican Airlines
Deal found 10/29$194

Cheap flight deals from Ontario to Chicago

Keep the following information in mind while searching for Ontario to Chicago flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$181
(SmartFares)

One-way from

$106
(lastminute.com)

Popular in

October

Cheapest in

July

Average price

$296

Good round-trip deal

$333 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
Search Deals
From Ontario to Chicago (CHI)
Search Deals
One-way flight from Ontario to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Ontario to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Ontario to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Ontario to Chicago 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 2,558,603 searches. Data last updated October 30, 2025.
Use the filters below to find and compare flights from Ontario to Chicago that are best for you.

Fly from

Ontario

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 1/16

2:15 pm-3:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 1/19

3:35 pm-11:04 pm

1 stop6h 29m

$183

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 2/27

3:30 pm-4:39 pm

Nonstop2h 09m

Chicago O'Hare Intl

Sun 3/1

4:47 pm-7:45 pm

Nonstop1h 58m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/24

8:55 am-10:02 am

Nonstop2h 07m

Chicago O'Hare Intl

Sat 2/28

8:15 pm-10:54 pm

Nonstop1h 39m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/26

6:30 pm-7:30 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sun 3/1

2:00 pm-4:39 pm

Nonstop1h 39m

$185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/22

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

$197

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 11/24

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 12/1

11:00 am-1:42 pm

Nonstop1h 42m

$199

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

$201

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/4

6:24 pm-7:24 pm

Nonstop2h 00m

Chicago O'Hare Intl

Fri 12/5

9:39 am-12:30 pm

Nonstop1h 51m

$202

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/18

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Tue 1/13

1:13 pm-4:02 pm

Nonstop1h 49m

$207

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/17

6:50 am-8:03 am

Nonstop2h 13m

Chicago O'Hare Intl

Wed 1/14

9:15 pm-11:59 pm

Nonstop1h 44m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 results
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Best time to book a flight from Ontario to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Ontario 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 Ontario to Chicago

What is the cheapest month to book a flight from Region of Ontario to Chicago?

Currently, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $83). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of $190). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ON to CHI?

Find hourly flight availability from Ontario to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 32% on flights from Region of Ontario to Chicago by exploring options for tickets at noon.

What is the cheapest day to fly from Region of Ontario to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Ontario to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Region of Ontario to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Ontario to Chicago. 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 Region of Ontario to Chicago?

    For as low as $197, Air Canada can have you in Chicago from Region of Ontario in 1h 50m. The distance between Region of Ontario and Chicago is about 442 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Region of Ontario to Chicago one-way?

    For one-way options, check prices for Porter Airlines. According to our data, you can fly for as low as $106. Users have also found prices from $132 and $134 on Air Canada and Delta, respectively.

  • What are the most popular routes from Region of Ontario to Chicago?

    While some choose either Toronto Pearson Intl - Chicago O'Hare Intl or Toronto Island - Chicago Midway, Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl is the most popular route from Region of Ontario to Chicago.

  • What are the most reliable airlines from Region of Ontario to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Region of Ontario to Chicago on time: EVA Air (94%), Egyptair (90%), Copa Airlines (90%).

  • What are the cheapest flights from Region of Ontario to Chicago?

    On average you can expect to pay $1,238 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $153 while the most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) is currently priced at $183.

  • Can I find deals for flights from Ontario to Chicago that include hotel bookings?

    Yes. In addition to deals on Ontario to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Ontario to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Ontario to Chicago.

  • Can I find deals for business class flights from Ontario to Chicago?

    Yes. Cheapflights offers flight deals from Ontario to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Region of Ontario to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $83). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of $190). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Ontario to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson Intl to O'Hare Intl flights
Toronto Island to Midway flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Calgary to O'Hare Intl flights
Pearson Intl to St. Louis flights
Ottawa to O'Hare Intl flights
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Vancouver Intl to Midway flights
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Ottawa to Midway flights
Calgary to Midway flights
Edmonton to O'Hare Intl flights
Edmonton to Midway flights
Winnipeg to Midway flights
Saskatoon to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Kelowna to O'Hare Intl flights
Halifax to O'Hare Intl flights
Québec City to Midway flights
Halifax to Midway flights
Grande Prairie to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Edmonton to St. Louis flights
Victoria to O'Hare Intl flights
Ottawa to St. Louis flights
Regina to O'Hare Intl flights
Pearson Intl to Peoria flights
Moncton to O'Hare Intl flights
London to O'Hare Intl flights
Halifax to St. Louis flights
Calgary to St. Louis flights
Victoria to Midway flights
Vancouver Intl to Peoria flights
Vancouver Intl to Paducah flights
London to Midway flights
St. John's to Midway flights
St John to O'Hare Intl flights
Ottawa to Bloomington flights

Top 5 airlines flying from Ontario to Chicago

Discover the top 5 airlines that operate flights from Ontario to Chicago. 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 2,558,603 searches. Data last updated October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$147Average$411FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$158Average$327FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$165Average$371FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$344FlexibilityNo cancel feeOn-time71%
WestJetCheapest$208Average$348FlexibilityNo cancel feeOn-time60%

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