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$103+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$149
(SmartFares)

One-way from

$103
(Booking.com)

Popular in

December

Cheapest in

June

Average price

$270

Good round-trip deal

$170 or less

Good one-way deal

$101 or less
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. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Air Canada deal was found by Cheapflights users on 7/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:05 pmYYZ - ORD
Nonstop1h 56mAir Canada
Sun 11/93:55 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 7/30$147
This SmartFares deal was found by Cheapflights users on 7/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 9/225:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/29$149
This Booking.com deal was found by Cheapflights users on 7/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:25 pmYTZ - ORD
1 stop5h 46mAir Canada
Sat 9/203:35 pmORD - YTZ
1 stop4h 59mAir Canada
Deal found 7/29$155
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/19:00 amYTZ - MDW
Nonstop1h 50mAir Transat
Wed 9/39:35 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 7/29$166
This Air Canada deal was found by Cheapflights users on 7/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/188:20 amYUL - ORD
Nonstop2h 31mAir Canada
Sun 9/218:40 amORD - YUL
Nonstop2h 17mAir Canada
Deal found 7/31$175
This Kissandfly.com deal was found by Cheapflights users on 7/30. 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 9/45:15 pmYYZ - ORD
Nonstop1h 57mLufthansa
Sun 9/79:12 pmORD - YYZ
Nonstop1h 46mLufthansa
Deal found 7/30$182
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 8/209:00 pmYYZ - ORD
Nonstop2h 07mUnited Airlines
Tue 9/29:12 pmORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 7/30$189
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:49 pmYYZ - ORD
1 stop6h 21mAmerican Airlines
Sun 10/125:22 amORD - YYZ
1 stop4h 48mAmerican Airlines
Deal found 7/29$196
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:50 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 9/295:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 7/29$196
This Flightnetwork deal was found by Cheapflights users on 7/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/310:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Sun 10/55:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 7/29$198
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/47:50 amYUL - ORD
1 stop5h 30mAmerican Airlines
Sun 9/77:00 amORD - YUL
1 stop14h 57mAmerican Airlines
Deal found 7/30$200
This Delta deal was found by Cheapflights users on 7/31. 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.
Mon 9/110:10 amYYZ - ORD
1 stop3h 35mDelta
Fri 9/269:10 amORD - YYZ
1 stop7h 13mDelta
Deal found 7/31$212

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 July 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

Tue 9/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Mon 9/22

5:20 pm-8:02 pm

Nonstop1h 42m

$149

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 9/13

3:25 pm-8:11 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 9/20

3:35 pm-9:34 pm

1 stop4h 59m

$155

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 9/13

4:00 pm-8:11 pm

1 stop5h 11m

Chicago O'Hare Intl

Sat 9/20

8:25 pm-11:08 pm

Nonstop1h 43m

$157

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 9/1

9:00 am-9:50 am

Nonstop1h 50m

Chicago Midway

Wed 9/3

9:35 am-12:17 pm

Nonstop1h 42m

$166

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/18

8:20 am-9:51 am

Nonstop2h 31m

Chicago O'Hare Intl

Sun 9/21

8:40 am-11:57 am

Nonstop2h 17m

$175

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/4

5:15 pm-6:12 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 9/7

9:12 pm-11:58 pm

Nonstop1h 46m

$182

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 8/20

9:00 pm-10:07 pm

Nonstop2h 07m

Chicago O'Hare Intl

Tue 9/2

9:12 pm-11:58 pm

Nonstop1h 46m

$189

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 10/7

3:49 pm-9:10 pm

1 stop6h 21m

Chicago O'Hare Intl

Sun 10/12

5:22 am-11:10 am

1 stop4h 48m

$196

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/25

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 9/29

5:20 pm-8:02 pm

Nonstop1h 42m

$196

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/3

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Sun 10/5

5:20 pm-10:15 pm

1 stop3h 55m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 $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 July 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 July 31, 2025.

The most flights from CAON to CHI are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

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 July 31, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, and Air Transat from Ontario to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
318 reviews

Comfort

8.0

Boarding

8.2

Crew

8.7

Entertainment

7.0

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 Air Canada. According to our data, you can fly for as low as $103. Users have also found prices from $103 and $106 on Porter Airlines and Air Transat, respectively.

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

    While some choose either Toronto Island - Chicago Midway 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: Cathay Pacific (100%), SkyWest Airlines (91%), Egyptair (90%).

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

    On average you can expect to pay $2,979 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $122 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $172.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$155Average$412FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$158Average$257FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$165Average$418FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$211Average$334FlexibilityNo cancel feeOn-time71%

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