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$116+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Sat 1/317:10 amORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 12/15$204
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:40 pmYYZ - ORD
1 stop5h 04mUnited Airlines
Mon 2/24:50 pmORD - YYZ
Nonstop1h 55mUnited Airlines
Deal found 12/15$210
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Sun 2/17:10 amORD - YYZ
1 stop5h 33mUnited Airlines
Deal found 12/15$214
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:40 pmYYZ - ORD
1 stop5h 55mUnited Airlines
Thu 1/18:51 amORD - YYZ
1 stop13h 55mUnited Airlines
Deal found 12/16$237
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:40 pmYYZ - ORD
1 stop5h 04mUnited Airlines
Fri 1/97:10 amORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 12/15$252
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/311:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$270
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 2/511:15 amORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 12/15$276
This FlightHub deal was found by Cheapflights users on 12/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/311:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$291
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:40 pmYYZ - ORD
1 stop5h 04mUnited Airlines
Tue 2/311:15 amORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 12/15$292
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
Sat 1/311:13 pmORD - YYZ
Nonstop1h 49mUnited Airlines
Deal found 12/15$301
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:25 pmYUL - ORD
1 stop17h 19mUnited Airlines
Mon 1/57:00 amORD - YUL
1 stop4h 46mUnited Airlines
Deal found 12/16$301
This FlightHub deal was found by Cheapflights users on 12/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Mon 2/2311:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/16$302

Find flight deals from Ontario to Chicago

Keep the following information in mind while searching for Ontario to Chicago flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$182
(American Airlines)

One-way from

$116
(Trip.com)

Popular in

December

Cheapest in

July

Average price

$321

Good round-trip deal

$210 or less

Good one-way deal

$117 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. 10% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 18, 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

Thu 2/5

9:00 am-10:06 am

Nonstop2h 06m

Chicago O'Hare Intl

Sun 2/8

9:15 pm-11:59 pm

Nonstop1h 44m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 1/26

11:00 am-1:42 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 2/9

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 2/10

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 1/23

11:05 am-1:47 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 1/24

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Thu 1/29

11:00 am-1:42 pm

Nonstop1h 42m

$188

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 2/15

6:00 pm-9:17 pm

Nonstop2h 17m

$189

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 2/6

6:00 am-8:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Mon 2/9

8:52 am-3:16 pm

1 stop5h 24m

$189

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 2/10

6:00 am-8:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Sat 2/14

6:00 pm-9:17 pm

Nonstop2h 17m

$189

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 2/11

4:45 pm-6:51 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sun 2/15

6:00 pm-9:17 pm

Nonstop2h 17m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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, April is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $82). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of $184). 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 December 18, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 34% 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 Monday evenings 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.

Weekly flight availability from Region of Ontario to Chicago

Explore weekly flight availability from Ontario to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 18, 2025.

The most flights from CAON to CHI are scheduled on a Wednesday (56 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (15 on average).

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 $186, United Airlines 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 $101. Users have also found prices from $108 and $109 on Air Canada and United Airlines, respectively.

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

    While some choose either Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Toronto Island - Chicago Midway, Toronto Pearson 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 (83%), Japan Airlines (80%), Egyptair (78%).

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

    On average you can expect to pay $1,110 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $129 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $155.

  • 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, April is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $82). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of $184). 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
Lansing
Merrillville
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.
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Top 4 airlines flying from Ontario to Chicago

Discover the top 4 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$150Average$406FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$158Average$340FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$165Average$402FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$195Average$345FlexibilityNo cancel feeOn-time71%

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