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$102+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$195
(Cheapflightsfares)

One-way from

$123
(Flightnetwork)

Popular in

December

Cheapest in

April

Average price

$249

Good round-trip deal

$189 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 ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 9/59:15 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/17$195
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/610:20 amYTZ - ORD
2 stops10h 52mAir Canada
Wed 5/148:40 amORD - YTZ
1 stop5h 10mAir Canada
Deal found 4/16$199
This Vakatrip 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 Vakatrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/912:00 pmYYZ - ORD
Nonstop1h 55mAir Canada
Sun 5/119:35 amORD - YYZ
Nonstop1h 40mAir Canada
Deal found 4/16$201
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.
Thu 5/222:45 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 5/273:50 pmORD - YYZ
Nonstop1h 42mUnited Airlines
Deal found 4/16$205
This United 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/49:00 amYYZ - ORD
Nonstop2h 01mMultiple Airlines
Sun 5/117:10 amORD - YYZ
Nonstop1h 48mMultiple Airlines
Deal found 4/16$215
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 6/79:40 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 4/16$218
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/63:35 pmYTZ - MDW
Nonstop1h 49mAir Transat
Wed 5/149:40 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 4/16$220
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/87:55 amYYZ - ORD
Nonstop1h 55mLufthansa
Sun 5/114:41 pmORD - YYZ
Nonstop1h 56mLufthansa
Deal found 4/16$221
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/318:00 amYUL - ORD
1 stop5h 55mAir Canada
Sat 6/73:50 pmORD - YUL
1 stop4h 50mAir Canada
Deal found 4/15$230
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/91:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Mon 5/129:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 4/15$231
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:15 amYYZ - ORD
1 stop5h 17mDelta
Wed 5/147:10 amORD - YYZ
1 stop3h 15mDelta
Deal found 4/16$235
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3112:15 pmYYZ - MDW
1 stop5h 06mDelta
Sat 6/75:25 pmMDW - YYZ
1 stop4h 33mDelta
Deal found 4/16$235

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 17, 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

Sat 5/10

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Fri 9/5

9:15 am-11:57 am

Nonstop1h 42m

$195

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 5/6

10:20 am-8:12 pm

2 stops10h 52m

Chicago O'Hare Intl

Wed 5/14

8:40 am-2:50 pm

1 stop5h 10m

$199

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 5/9

12:00 pm-12:55 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 5/11

9:35 am-12:15 pm

Nonstop1h 40m

$201

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/22

2:45 pm-3:50 pm

Nonstop2h 05m

Chicago O'Hare Intl

Tue 5/27

3:50 pm-6:32 pm

Nonstop1h 42m

$205

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 5/4

9:00 am-10:01 am

Nonstop2h 01m

Chicago O'Hare Intl

Sun 5/11

7:10 am-9:58 am

Nonstop1h 48m

$215

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 5/31

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Sat 6/7

9:40 am-12:22 pm

Nonstop1h 42m

$218

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 5/6

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Wed 5/14

9:40 am-12:22 pm

Nonstop1h 42m

$220

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/8

7:55 am-8:50 am

Nonstop1h 55m

Chicago O'Hare Intl

Sun 5/11

4:41 pm-7:37 pm

Nonstop1h 56m

$221

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 5/31

8:00 am-12:55 pm

1 stop5h 55m

Chicago O'Hare Intl

Sat 6/7

3:50 pm-9:40 pm

1 stop4h 50m

$230

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/9

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Mon 5/12

9:40 am-4:00 pm

1 stop5h 20m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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 $321). 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 17, 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 April 17, 2025.

The most flights from CAON to CHI are scheduled on a Thursday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 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 April 17, 2025.
Get a feel of what it's like to fly with ANA, Porter Airlines and Delta 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.
ANA
8.3
Very good
845 reviews

Boarding

8.5

Comfort

8.1

Crew

8.7

Entertainment

7.9

Food

7.6

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
ANA
8.3
Very good
845 reviews
ANA
8.3
Very good
845 reviews

Boarding

8.5

Comfort

8.1

Crew

8.7

Entertainment

7.9

Food

7.6

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Porter Airlines
8.0
Very good
281 reviews
ANA
8.3
Very good
845 reviews

Boarding

8.5

Comfort

8.1

Crew

8.7

Entertainment

7.9

Food

7.6

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Delta
8.0
Very good
7,916 reviews
ANA
8.3
Very good
845 reviews

Boarding

8.5

Comfort

8.1

Crew

8.7

Entertainment

7.9

Food

7.6

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Air Transat
7.8
Good
385 reviews
ANA
8.3
Very good
845 reviews

Boarding

8.5

Comfort

8.1

Crew

8.7

Entertainment

7.9

Food

7.6

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
United Airlines
7.4
Good
8,667 reviews
ANA
8.3
Very good
845 reviews

Boarding

8.5

Comfort

8.1

Crew

8.7

Entertainment

7.9

Food

7.6

Overall

8.3

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.

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 $123. Users have also found prices from $124 and $134 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 Pearson Intl - 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 (90%), Egyptair (89%), ANA (85%).

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

    On average you can expect to pay $528 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $127 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $201.

  • 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 $321). 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
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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$170Average$348FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$196Average$423FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$227Average$461FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$327FlexibilityNo cancel feeOn-time71%

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