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$143+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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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 November 21, 2024.

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 November 21, 2024.

This oojo deal was found by Cheapflights users on 11/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/129:40 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 12/265:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/20$228
This United Airlines deal was found by Cheapflights users on 11/20. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/122:00 pmYYZ - ORD
Nonstop1h 51mUnited Airlines
Mon 12/168:25 pmORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 11/20$245
This Air Canada deal was found by Cheapflights users on 11/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/135:30 pmYYZ - ORD
Nonstop2h 07mAir Canada
Sun 12/157:19 amORD - YYZ
Nonstop1h 39mAir Canada
Deal found 11/21$246
This Flysmarter deal was found by Cheapflights users on 11/20. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/132:05 pmYYZ - ORD
1 stop5h 31mMultiple Airlines
Tue 12/176:38 pmORD - YYZ
Nonstop1h 47mMultiple Airlines
Deal found 11/20$259
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1210:25 amYTZ - ORD
1 stop5h 20mAir Canada
Sun 12/152:01 pmORD - YTZ
1 stop4h 49mAir Canada
Deal found 11/19$261
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/129:40 amYTZ - MDW
Nonstop1h 50mAir Transat
Sun 12/1511:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/20$262
This Kissandfly.com deal was found by Cheapflights users on 11/20. 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.
Thu 12/126:52 amYYZ - ORD
Nonstop2h 13mLufthansa
Sun 12/157:19 amORD - YYZ
Nonstop1h 39mLufthansa
Deal found 11/20$266
This CheapTicketsDeal deal was found by Cheapflights users on 11/20. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:30 amYYZ - MDW
1 stop13h 02mWestJet
Mon 12/169:38 amMDW - YYZ
1 stop12h 56mWestJet
Deal found 11/20$267
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/127:30 amYUL - ORD
1 stop16h 15mAmerican Airlines
Mon 12/162:55 pmORD - YUL
1 stop18h 10mAmerican Airlines
Deal found 11/20$281
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:30 amYYZ - ORD
1 stop9h 08mDelta
Thu 1/1612:35 pmORD - YYZ
1 stop6h 56mDelta
Deal found 11/19$285
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/86:00 amYYZ - ORD
1 stop7h 30mAmerican Airlines
Wed 12/116:00 amORD - YYZ
1 stop4h 56mAmerican Airlines
Deal found 11/20$290
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/1210:05 amYYZ - MDW
1 stop7h 56mDelta
Mon 12/161:30 pmMDW - YYZ
1 stop8h 06mDelta
Deal found 11/20$294

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

9:40 am-10:30 am

Nonstop1h 50m

Chicago Midway

Thu 12/26

5:35 pm-8:17 pm

Nonstop1h 42m

$228

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

2:00 pm-2:51 pm

Nonstop1h 51m

Chicago O'Hare Intl

Mon 12/16

8:25 pm-11:06 pm

Nonstop1h 41m

$245

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/13

5:30 pm-6:37 pm

Nonstop2h 07m

Chicago O'Hare Intl

Sun 12/15

7:19 am-9:58 am

Nonstop1h 39m

$246

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/13

2:05 pm-6:36 pm

1 stop5h 31m

Chicago O'Hare Intl

Tue 12/17

6:38 pm-9:25 pm

Nonstop1h 47m

$259

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 12/12

10:25 am-2:45 pm

1 stop5h 20m

Chicago O'Hare Intl

Sun 12/15

2:01 pm-7:50 pm

1 stop4h 49m

$261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

9:40 am-10:30 am

Nonstop1h 50m

Chicago Midway

Sun 12/15

11:15 am-1:57 pm

Nonstop1h 42m

$262

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

6:52 am-8:05 am

Nonstop2h 13m

Chicago O'Hare Intl

Sun 12/15

7:19 am-9:58 am

Nonstop1h 39m

$266

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/12

6:30 am-6:32 pm

1 stop13h 02m

Chicago Midway

Mon 12/16

9:38 am-11:34 pm

1 stop12h 56m

$267

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 12/12

7:30 am-10:45 pm

1 stop16h 15m

Chicago O'Hare Intl

Mon 12/16

2:55 pm-10:05 am

1 stop18h 10m

$281

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 12/31

6:30 am-2:38 pm

1 stop9h 08m

Chicago O'Hare Intl

Thu 1/16

12:35 pm-8:31 pm

1 stop6h 56m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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.

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, September is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $232). Flying from Region of Ontario to Chicago in June is currently the most expensive (average of $308). 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 November 21, 2024.

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 November 21, 2024.

The most flights from CAON to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 November 21, 2024.
Get a feel of what it's like to fly with United Airlines, Air Canada 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
8,758 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

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
8,758 reviews
Delta
8.0
Very good
8,758 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

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
7.8
Good
286 reviews
Delta
8.0
Very good
8,758 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

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
389 reviews
Delta
8.0
Very good
8,758 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

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
9,172 reviews
Delta
8.0
Very good
8,758 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 10

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

WestJet
7.3
Good
2,810 reviews
Delta
8.0
Very good
8,758 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

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 $143. Users have also found prices from $147 and $152 on United Airlines and Air Canada, 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: Egyptair (100%), Jazz (100%), Lufthansa (100%).

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

    On average you can expect to pay $894 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $145 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $262.

  • 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, September is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of $232). Flying from Region of Ontario to Chicago in June is currently the most expensive (average of $308). 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.

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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.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
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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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$157Average$371FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$205Average$294FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$219Average$447FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$327FlexibilityNo cancel feeOn-time71%
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