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$115+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
May 19 — May 261
Tue 5/19
Tue 5/26
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 April 19, 2026.

This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 6/710:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 4/15$186
This Booking.com deal was found by Cheapflights users on 4/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:30 am
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Fri 5/293:20 pm
MDW
-
YUL
1 stop3h 50m
Porter Airlines
Deal found 4/16$190
This Cheapflightsfares deal was found by Cheapflights users on 4/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 5/83:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/19$204
This Mytrip deal was found by Cheapflights users on 4/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:40 pm
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 9/611:45 am
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/18$204
This Air Canada deal was found by Cheapflights users on 4/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:25 pm
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Sun 5/319:55 am
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 4/15$205
This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 5/2010:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/15$205
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Fri 5/2211:00 am
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Mon 5/259:15 pm
ORD
-
YYZ
Nonstop1h 44m
United Airlines
Deal found 4/16$206
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Sat 5/98:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/1010:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/14$206
This Air Canada deal was found by Cheapflights users on 4/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/257:20 pm
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Wed 7/17:25 am
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 4/17$206
This Kissandfly.com deal was found by Cheapflights users on 4/18. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/1010:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/18$207
This Justfly.com deal was found by Cheapflights users on 4/17. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:40 pm
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Mon 9/283:20 pm
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/17$207
This Air Canada deal was found by Cheapflights users on 4/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:30 am
YYZ
-
ORD
1 stop5h 23m
Air Canada
Tue 5/129:55 am
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 4/17$208

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 April 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$186
(Trip.com)

One-way from

$115
(Trip.com)

Popular in

April

Cheapest in

July

Average price

$319

Good round-trip deal

$178 or less

Good one-way deal

$102 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. 8% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 19, 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
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 5/26

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Sun 5/31

10:30 am-1:10 pm

Nonstop1h 40m

$207

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 8/21

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Mon 8/24

10:25 am-1:05 pm

Nonstop1h 40m

$208

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/10

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Thu 5/14

10:30 am-1:10 pm

Nonstop1h 40m

$217

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 5/20

1:00 pm-2:01 pm

Nonstop2h 01m

Chicago O'Hare Intl

Wed 5/27

7:09 am-9:54 am

Nonstop1h 45m

$229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/14

9:00 pm-10:01 pm

Nonstop2h 01m

Chicago O'Hare Intl

Sat 5/30

2:21 pm-10:23 pm

1 stop7h 02m

$229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 5/4

9:00 pm-10:01 pm

Nonstop2h 01m

Chicago O'Hare Intl

Wed 5/6

5:00 am-11:43 am

1 stop5h 43m

$229

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 5/7

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Thu 5/7

3:20 pm-6:00 pm

Nonstop1h 40m

$229

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Fri 5/8

4:04 pm-6:33 pm

1 stop3h 29m

Chicago Midway

Wed 5/13

9:22 am-1:30 pm

1 stop3h 08m

$230

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/29

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Sun 5/31

3:20 pm-6:00 pm

Nonstop1h 40m

$232

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/29

9:25 am-10:15 am

Nonstop1h 50m

Chicago Midway

Fri 5/1

10:30 am-1:10 pm

Nonstop1h 40m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 60 resultsSorted by cheapest first
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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, August is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $225). Flying from Region of Ontario to Chicago in January is currently the most expensive (average of $779). 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 April 19, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 11% 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 April 18, 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 April 19, 2026.

The most flights from CAON to CHI are scheduled on a Sunday (71 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (45 on average).

How much does it cost to fly round-trip from Region of Ontario to Chicago?

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 $207, Porter 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. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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: Copa Airlines (91%), EVA Air (78%), Republic Airways (73%).

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

    On average you can expect to pay $560 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $128 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $199.

  • 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, August is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $225). Flying from Region of Ontario to Chicago in January is currently the most expensive (average of $779). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 April 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$80Average$355FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$146Average$274FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$423FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$295FlexibilityNo cancel feeOn-time71%

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