HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$134+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Discover tips and strategies to find the most affordable flight options for your journey from Ontario (CAON) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$236
(Cheapflightsfares)

One-way from

$134
(iWofly)
From Ontario to Chicago (CHI)
Search Deals
One-way flight from Ontario to Chicago (CHI)
Search Deals

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 enero 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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.
jue. 2/1311:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 2/171:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/21$236
This American Airlines deal was found by Cheapflights users on 1/21. 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.
sáb. 3/111:31 amYYZ - ORD
Nonstop2h 00mAmerican Airlines
mié. 3/58:11 amORD - YYZ
Nonstop1h 40mAmerican Airlines
Deal found 1/21$238
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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.
vie. 3/149:30 amYTZ - MDW
Nonstop1h 50mAir Transat
dom. 3/1611:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 1/20$243
This Trip.com deal was found by Cheapflights users on 1/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 2/98:35 amYOW - MDW
1 stop4h 35mPorter Airlines
jue. 2/131:05 pmMDW - YOW
1 stop6h 29mPorter Airlines
Deal found 1/19$244
This Air Canada deal was found by Cheapflights users on 1/20. 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.
jue. 2/139:00 pmYYZ - ORD
Nonstop2h 06mAir Canada
jue. 2/202:05 pmORD - YYZ
Nonstop1h 41mAir Canada
Deal found 1/20$246
This United deal was found by Cheapflights users on 1/20. 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.
mié. 2/126:40 pmYYZ - ORD
Nonstop1h 57mMultiple Airlines
sáb. 2/229:50 amORD - YYZ
Nonstop1h 35mMultiple Airlines
Deal found 1/20$247
This Air Canada deal was found by Cheapflights users on 1/20. 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.
vie. 2/148:50 amYTZ - ORD
1 stop5h 09mAir Canada
dom. 2/233:35 pmORD - YTZ
1 stop5h 15mAir Canada
Deal found 1/20$250
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/1211:20 amYTZ - MDW
1 stop8h 03mMultiple Airlines
jue. 2/131:05 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 1/19$253
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/126:45 amYTZ - ORD
1 stop5h 20mMultiple Airlines
jue. 2/135:15 amORD - YTZ
1 stop5h 25mMultiple Airlines
Deal found 1/19$257
This Delta deal was found by Cheapflights users on 1/20. 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.
jue. 2/136:00 amYYZ - ORD
1 stop4h 16mDelta
sáb. 2/154:58 pmORD - YYZ
1 stop4h 51mDelta
Deal found 1/20$266
This Delta deal was found by Cheapflights users on 1/20. 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.
jue. 2/136:00 amYYZ - MDW
1 stop3h 51mDelta
mié. 2/199:33 amMDW - YYZ
1 stop5h 36mDelta
Deal found 1/20$266
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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.
jue. 2/136:00 amYYZ - MDW
1 stop3h 51mKLM
dom. 2/169:33 amMDW - YYZ
1 stop5h 36mKLM
Deal found 1/20$281

Find flights from Ontario to Chicago within your budget

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 2/6

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

sáb. 2/8

1:05 pm-3:47 pm

Nonstop1h 42m

$237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

lun. 3/3

11:31 am-12:31 pm

Nonstop2h 00m

Chicago O'Hare Intl

lun. 3/10

3:00 pm-5:30 pm

Nonstop1h 30m

$238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 3/14

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

dom. 3/16

11:15 am-1:57 pm

Nonstop1h 42m

$243

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

dom. 2/9

8:35 am-12:10 pm

1 stop4h 35m

Chicago Midway

jue. 2/13

1:05 pm-8:34 pm

1 stop6h 29m

$244

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 2/21

6:52 am-8:01 am

Nonstop2h 09m

Chicago O'Hare Intl

dom. 2/23

9:12 pm-11:59 pm

Nonstop1h 47m

$246

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mié. 2/12

6:40 pm-7:37 pm

Nonstop1h 57m

Chicago O'Hare Intl

sáb. 2/22

9:50 am-12:25 pm

Nonstop1h 35m

$247

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

vie. 2/14

8:50 am-12:59 pm

1 stop5h 09m

Chicago O'Hare Intl

dom. 2/23

3:35 pm-9:50 pm

1 stop5h 15m

$250

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 2/12

11:20 am-6:23 pm

1 stop8h 03m

Chicago Midway

dom. 2/16

1:05 pm-3:47 pm

Nonstop1h 42m

$253

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

mié. 2/12

6:45 am-11:05 am

1 stop5h 20m

Chicago O'Hare Intl

jue. 2/13

5:15 am-11:40 am

1 stop5h 25m

$257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 2/13

6:00 am-9:16 am

1 stop4h 16m

Chicago O'Hare Intl

sáb. 2/15

4:58 pm-10:49 pm

1 stop4h 51m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 60 results
1
2
3
...
6

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.

Travel insights for flights from Ontario to Chicago

Get recent, data-driven insights about flights from Ontario to Chicago including ideal travel times, pricing trends, and more.

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 $320). 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 enero 21, 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 enero 21, 2025.

The most flights from CAON to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 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 enero 21, 2025.
Get a feel of what it's like to fly with Air Canada, WestJet and American 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.
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,982 reviews
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 $134. Users have also found prices from $147 and $149 on Air Canada and American 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: Emirates (92%), Japan Airlines (92%), Republic Airways (90%).

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

    On average you can expect to pay $682 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $153 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $251.

  • 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 $320). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Ontario to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Pearson Intl to Midway flights
Toronto Island to O'Hare Intl flights
Pearson Intl to St. Louis flights
Ottawa to O'Hare Intl flights
Calgary to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Vancouver Intl to Midway flights
Ottawa to Midway flights
Edmonton to O'Hare Intl flights
Calgary to Midway flights
Winnipeg to Midway flights
Québec City to O'Hare Intl flights
Québec City to Midway flights
Abbotsford to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Edmonton to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Halifax to O'Hare Intl flights
Halifax to Midway flights
Regina to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Edmonton to St. Louis flights
Calgary to St. Louis flights
St John to O'Hare Intl flights
Victoria to Midway flights
St. John's to Midway flights
Ottawa to St. Louis flights
Pearson Intl to Peoria flights
Saskatoon to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Victoria to O'Hare Intl flights
Winnipeg to St. Louis flights
Vancouver Intl to Paducah flights
Edmonton to Moline flights
Moncton to O'Hare Intl flights
Halifax to St. Louis flights
Victoria to St. Louis flights
Charlottetown to St. Louis flights
London to Midway flights
Comox to O'Hare Intl flights

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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$206Average$423FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$209Average$318FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$219Average$432FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$238Average$326FlexibilityNo cancel feeOn-time71%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.