HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$111+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Ontario to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 23, 2026.

This Justfly.com deal was found by Cheapflights users on 3/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 5/1010:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 3/18$175
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/269:50 am
YUL
-
MDW
1 stop6h 30m
Porter Airlines
Mon 4/2711:00 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 3/18$182
This Trip.com deal was found by Cheapflights users on 3/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:30 am
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Sun 5/1010:30 am
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 3/22$183
This Trip.com deal was found by Cheapflights users on 3/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:30 pm
YUL
-
ORD
Nonstop2h 38m
Air Canada
Mon 5/113:40 pm
ORD
-
YUL
Nonstop2h 24m
Air Canada
Deal found 3/20$189
This FlightHub deal was found by Cheapflights users on 3/18. 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.
Mon 6/16:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 6/83:20 pm
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 3/18$190
This Trip.com deal was found by Cheapflights users on 3/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/44:30 pm
YUL
-
ORD
1 stop4h 46m
Air Canada
Sun 6/77:25 am
ORD
-
YUL
1 stop5h 20m
Air Canada
Deal found 3/22$191
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 5/286:30 am
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Sun 5/3110:30 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 3/22$191
This Kiwi.com deal was found by Cheapflights users on 3/18. 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.
Tue 4/219:25 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 4/2811:00 am
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 3/18$192
This Trip.com deal was found by Cheapflights users on 3/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:15 am
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 4/128:40 am
ORD
-
YUL
Nonstop2h 11m
Air Canada
Deal found 3/21$192
This Jettzy deal was found by Cheapflights users on 3/17. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 5/910:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 3/17$193
This Trip.com deal was found by Cheapflights users on 3/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:40 am
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 5/108:45 am
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 3/18$193
This Trip.com deal was found by Cheapflights users on 3/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:15 am
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 4/1912:50 pm
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 3/22$194

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$175
(Justfly.com)

One-way from

$111
(SmartFares)

Popular in

December

Cheapest in

July

Average price

$270

Good round-trip deal

$278 or less

Good one-way deal

$127 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. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 23, 2026.
Use the filters below to find and compare flights from Ontario to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 6/18

7:20 pm-8:16 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 6/21

7:25 am-10:06 am

Nonstop1h 41m

$197

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 5/1

6:10 am-8:00 am

Nonstop2h 50m

Chicago O'Hare Intl

Mon 5/25

7:10 am-10:40 am

Nonstop2h 30m

$200
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 5/2

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Mon 5/4

3:20 pm-6:00 pm

Nonstop1h 40m

$200

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 6/6

9:45 am-11:20 am

Nonstop2h 35m

Chicago O'Hare Intl

Fri 6/12

5:00 am-1:09 pm

1 stop7h 09m

$210

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 7/16

12:45 pm-11:26 pm

1 stop11h 41m

Chicago O'Hare Intl

Mon 7/20

9:40 pm-10:04 am

1 stop11h 24m

$214

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/10

2:15 pm-8:24 pm

1 stop7h 09m

Chicago O'Hare Intl

Mon 7/13

7:10 am-3:18 pm

1 stop7h 08m

$224

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 4/28

9:25 am-10:15 am

Nonstop1h 50m

Chicago Midway

Wed 4/29

11:00 am-1:42 pm

Nonstop1h 42m

$225

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 5/7

6:30 am-9:45 am

1 stop4h 15m

Chicago Midway

Thu 5/14

10:30 am-8:10 pm

1 stop8h 40m

$229

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 6/12

6:10 am-7:50 am

Nonstop2h 40m

Chicago O'Hare Intl

Mon 6/15

5:00 am-1:09 pm

1 stop7h 09m

$229

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/18

5:00 pm-6:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Sat 4/25

7:00 am-1:09 pm

1 stop5h 09m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 $177). 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 March 23, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 19% 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 March 14, 2026.

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. Saturday 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 March 23, 2026.

The most flights from CAON to CHI are scheduled on a Friday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (51 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 $200, 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 $101. Users have also found prices from $108 and $110 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: Emirates (100%), Copa Airlines (85%), Republic Airways (75%).

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

    On average you can expect to pay $793 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $130 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $189.

  • 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 $177). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$80Average$357FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$146Average$265FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$422FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$320FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.