$108+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
juin 17 — juin 241
1 adult, Economy
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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
Keep the following information in mind while searching for Ontario to Chicago flight deals. Data was last updated juin 12, 2025.
Round-trip from | $161 (iWofly) |
|---|---|
One-way from | $108 (Air Canada) |
Popular in | December |
Cheapest in | April |
Average price | $253 |
Good round-trip deal | $170 or less |
Good one-way deal | $100 or less |
Find flight deals from Ontario to Chicago
Cheapest flights from Ontario to ChicagoExplore 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 juin 12, 2025.
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 juin 12, 2025.
This iWofly deal was found by Cheapflights users on 6/12. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 6/267:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
dim. 6/299:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12![Porter Airlines logo]()
$161
This United Airlines deal was found by Cheapflights users on 6/12. 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.
ven. 9/197:00 amYYZ - ORD
Nonstop1h 59mUnited Airlines
lun. 9/229:12 pmORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 6/12![United Airlines logo]()
$164
This Air Canada deal was found by Cheapflights users on 6/12. 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.
mer. 9/108:15 amYYZ - ORD
Nonstop1h 53mAir Canada
ven. 9/126:20 pmORD - YYZ
Nonstop1h 42mAir Canada
Deal found 6/12![Air Canada logo]()
$165
This SmartFares deal was found by Cheapflights users on 6/11. 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.
sam. 8/307:55 amYTZ - MDW
Nonstop1h 50mAir Transat
ven. 9/129:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 6/11![Air Transat logo]()
$186
This KAYAK deal was found by Cheapflights users on 6/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/303:45 pmYYZ - ORD
1 stop5h 42mAmerican Airlines
jeu. 10/29:48 amORD - YYZ
1 stop6h 27mAmerican Airlines
Deal found 6/10![American Airlines logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
lun. 8/187:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
mar. 8/195:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$205
This Air Canada deal was found by Cheapflights users on 6/11. 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.
sam. 10/410:25 amYTZ - ORD
1 stop5h 30mAir Canada
mer. 10/1510:40 amORD - YTZ
1 stop5h 05mAir Canada
Deal found 6/11![Air Canada logo]()
$207
This Kissandfly.com deal was found by Cheapflights users on 6/11. 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.
jeu. 7/37:00 amYYZ - ORD
Nonstop1h 59mLufthansa
lun. 7/79:14 pmORD - YYZ
Nonstop1h 44mLufthansa
Deal found 6/11![Lufthansa logo]()
$209
This Delta deal was found by Cheapflights users on 6/11. 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.
sam. 10/412:15 pmYYZ - MDW
1 stop7h 21mDelta
mer. 10/159:30 amMDW - YYZ
1 stop6h 53mDelta
Deal found 6/11![Delta logo]()
$213
This Delta deal was found by Cheapflights users on 6/9. 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.
ven. 7/45:04 pmYYZ - ORD
1 stop6h 17mDelta
dim. 7/69:00 amORD - YYZ
1 stop7h 15mDelta
Deal found 6/9![Delta logo]()
$219
This FlightHub deal was found by Cheapflights users on 6/10. 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.
ven. 7/111:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
dim. 7/139:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 6/10![Porter Airlines logo]()
$226
This Air Canada deal was found by Cheapflights users on 6/10. 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.
mer. 8/271:20 pmYUL - ORD
Nonstop2h 35mAir Canada
mer. 9/38:40 amORD - YUL
Nonstop2h 17mAir Canada
Deal found 6/10![Air Canada logo]()
$227
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 juin 12, 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
jeu. 6/26
7:55 am-8:45 am
Nonstop1h 50m
Chicago Midway
dim. 6/29
9:40 am-12:22 pm
Nonstop1h 42m
$161
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
ven. 9/19
7:00 am-7:59 am
Nonstop1h 59m
Chicago O'Hare Intl
lun. 9/22
9:12 pm-11:58 pm
Nonstop1h 46m
$164
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
mer. 9/10
8:15 am-9:08 am
Nonstop1h 53m
Chicago O'Hare Intl
ven. 9/12
6:20 pm-9:02 pm
Nonstop1h 42m
$165
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
sam. 8/30
7:55 am-8:45 am
Nonstop1h 50m
Chicago Midway
ven. 9/12
9:15 am-11:57 am
Nonstop1h 42m
$186
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
mar. 9/30
3:45 pm-8:27 pm
1 stop5h 42m
Chicago O'Hare Intl
jeu. 10/2
9:48 am-5:15 pm
1 stop6h 27m
$191
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
lun. 8/18
7:55 am-8:45 am
Nonstop1h 50m
Chicago Midway
mar. 8/19
5:20 pm-8:02 pm
Nonstop1h 42m
$205
TorontoChicago
YTZ - ORD
YTZORD
Toronto Island
sam. 8/30
3:25 pm-8:16 pm
1 stop5h 51m
Chicago O'Hare Intl
ven. 9/12
10:40 am-4:45 pm
1 stop5h 05m
$207
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
jeu. 7/3
7:00 am-7:59 am
Nonstop1h 59m
Chicago O'Hare Intl
lun. 7/7
9:14 pm-11:58 pm
Nonstop1h 44m
$209
TorontoChicago
YYZ - MDW
YYZMDW
Toronto Pearson Intl
sam. 10/4
12:15 pm-6:36 pm
1 stop7h 21m
Chicago Midway
mer. 10/15
9:30 am-5:23 pm
1 stop6h 53m
$213
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
ven. 7/4
5:04 pm-10:21 pm
1 stop6h 17m
Chicago O'Hare Intl
dim. 7/6
9:00 am-5:15 pm
1 stop7h 15m
$219
Showing 1-10 of 60 results
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 juin 12, 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 juin 12, 2025.
The most flights from CAON to CHI are scheduled on a Wednesday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 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 juin 12, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and KLM 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.
Food
7.6
Boarding
8.2
Crew
8.7
Entertainment
7.0
Comfort
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Food
7.6
Boarding
8.2
Crew
8.7
Entertainment
7.0
Comfort
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Food
7.6
Boarding
8.2
Crew
8.7
Entertainment
7.0
Comfort
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Food
7.6
Boarding
8.2
Crew
8.7
Entertainment
7.0
Comfort
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Food
7.6
Boarding
8.2
Crew
8.7
Entertainment
7.0
Comfort
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
Food
7.6
Boarding
8.2
Crew
8.7
Entertainment
7.0
Comfort
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkayMary,Jun 2025
FLL - YYZ
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.
Traveling to a place near Ontario?
Book flights to Ontario if you plan to visit one of these locationsMerrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton
Browse thousands of different options on Cheapflights for your next trip
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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.
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 juin 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$162 | Average$410 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$165 | Average$446 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$169 | Average$252 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$218 | Average$318 | FlexibilityNo cancel fee | On-time71% |