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$124+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(Trip.com)

One-way from

$124
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$279

Good round-trip deal

$180 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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From Ontario to Chicago (CHI)
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One-way flight from Ontario to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Ontario to Chicago (CHI).
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Price to beat on a one-way flight from Ontario to Chicago (CHI).
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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 March 31, 2025.

This Trip.com deal was found by Cheapflights users on 3/31. 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 4/239:30 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 4/3011:15 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/31$199
This Booking.com deal was found by Cheapflights users on 3/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1410:00 amYYZ - ORD
Nonstop1h 54mAir Canada
Wed 5/218:25 pmORD - YYZ
Nonstop1h 42mAir Canada
Deal found 3/30$213
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/158:25 amYTZ - ORD
1 stop7h 22mAir Canada
Thu 5/222:07 pmORD - YTZ
1 stop6h 28mAir Canada
Deal found 3/30$219
This United deal was found by Cheapflights users on 3/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/247:00 amYYZ - ORD
Nonstop2h 03mMultiple Airlines
Sun 4/277:20 amORD - YYZ
1 stop5h 19mMultiple Airlines
Deal found 3/30$234
This Air Canada deal was found by Cheapflights users on 3/29. 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.
Sat 4/196:20 pmYUL - ORD
Nonstop2h 40mAir Canada
Sun 4/201:56 pmORD - YUL
1 stop6h 45mAir Canada
Deal found 3/29$237
This FlightHub deal was found by Cheapflights users on 3/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2110:45 amYUL - MDW
1 stop6h 55mPorter Airlines
Tue 4/295:35 pmMDW - YUL
1 stop4h 12mPorter Airlines
Deal found 3/29$240
This Gotogate deal was found by Cheapflights users on 3/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/144:05 pmYTZ - MDW
Nonstop1h 49mAir Transat
Wed 5/219:40 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 3/30$243
This Kissandfly.com deal was found by Cheapflights users on 3/30. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/247:00 amYYZ - ORD
Nonstop2h 03mLufthansa
Sun 4/279:02 amORD - YYZ
Nonstop1h 47mLufthansa
Deal found 3/30$245
This Trip.com deal was found by Cheapflights users on 3/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/13:35 pmYTZ - MDW
Nonstop1h 49mMultiple Airlines
Sun 5/49:40 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 3/30$248
This United deal was found by Cheapflights users on 3/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/229:15 amYUL - ORD
Nonstop2h 32mMultiple Airlines
Wed 4/231:56 pmORD - YUL
1 stop6h 45mMultiple Airlines
Deal found 3/30$250
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/112:00 pmYYZ - ORD
Nonstop1h 55mUnited Airlines
Sun 5/48:50 amORD - YYZ
1 stop7h 19mUnited Airlines
Deal found 3/30$253
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/256:00 amYYZ - ORD
1 stop4h 21mDelta
Sun 4/276:45 amORD - YYZ
1 stop3h 40mDelta
Deal found 3/31$259

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 31, 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

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/23

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Wed 4/30

11:15 am-1:57 pm

Nonstop1h 42m

$199

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 5/14

10:00 am-10:54 am

Nonstop1h 54m

Chicago O'Hare Intl

Wed 5/21

8:25 pm-11:07 pm

Nonstop1h 42m

$213

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 5/15

8:25 am-2:47 pm

1 stop7h 22m

Chicago O'Hare Intl

Thu 5/22

2:07 pm-9:35 pm

1 stop6h 28m

$219

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/24

7:00 am-8:03 am

Nonstop2h 03m

Chicago O'Hare Intl

Sun 4/27

7:20 am-1:39 pm

1 stop5h 19m

$234

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/19

6:20 pm-8:00 pm

Nonstop2h 40m

Chicago O'Hare Intl

Sun 4/20

1:56 pm-9:41 pm

1 stop6h 45m

$237

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 4/21

10:45 am-4:40 pm

1 stop6h 55m

Chicago Midway

Tue 4/29

5:35 pm-10:47 pm

1 stop4h 12m

$240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/14

4:05 pm-4:54 pm

Nonstop1h 49m

Chicago Midway

Wed 5/21

9:40 am-12:22 pm

Nonstop1h 42m

$243

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/24

7:00 am-8:03 am

Nonstop2h 03m

Chicago O'Hare Intl

Sun 4/27

9:02 am-11:49 am

Nonstop1h 47m

$245

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 5/1

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Sun 5/4

9:40 am-12:22 pm

Nonstop1h 42m

$248

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 4/22

9:15 am-10:47 am

Nonstop2h 32m

Chicago O'Hare Intl

Wed 4/23

1:56 pm-9:41 pm

1 stop6h 45m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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, August is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $245). Flying from Region of Ontario to Chicago in March is currently the most expensive (average of $323). 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 31, 2025.

When flying from Region of Ontario to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 31, 2025.

The most flights from CAON to CHI are scheduled on a Sunday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated March 31, 2025.
Get a feel of what it's like to fly with Japan Airlines, Delta and Porter Airlines from Ontario to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Japan Airlines
8.3
Very good
1,440 reviews

Boarding

8.4

Comfort

8.2

Crew

8.7

Food

7.7

Entertainment

7.8

Overall

8.3

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Japan Airlines
8.3
Very good
1,440 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Boarding

8.4

Comfort

8.2

Crew

8.7

Food

7.7

Entertainment

7.8

Overall

8.3

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Delta
8.0
Very good
7,899 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Boarding

8.4

Comfort

8.2

Crew

8.7

Food

7.7

Entertainment

7.8

Overall

8.3

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Porter Airlines
7.9
Good
277 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Boarding

8.4

Comfort

8.2

Crew

8.7

Food

7.7

Entertainment

7.8

Overall

8.3

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
KLM
7.8
Good
1,321 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Boarding

8.4

Comfort

8.2

Crew

8.7

Food

7.7

Entertainment

7.8

Overall

8.3

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Air Transat
7.8
Good
381 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Boarding

8.4

Comfort

8.2

Crew

8.7

Food

7.7

Entertainment

7.8

Overall

8.3

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

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.

  • 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 $124. Users have also found prices from $135 and $139 on Air Canada and United Airlines, respectively.

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

    While some choose either Toronto Island - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl, 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 (88%), Emirates (87%), ANA (86%).

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

    On average you can expect to pay $2,224 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $133 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $229.

  • 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 $245). Flying from Region of Ontario to Chicago in March is currently the most expensive (average of $323). 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 Ontario?

Book flights to Ontario if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$170Average$347FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$201Average$423FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$233Average$457FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$328FlexibilityNo cancel feeOn-time71%
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