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$131+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$205
(Trip.com)

One-way from

$131
(123 Milhas)

Popular in

December

Cheapest in

April

Average price

$285

Good round-trip deal

$228 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 ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

This Kissandfly.com deal was found by Cheapflights users on 2/22. 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.
Sat 3/1511:10 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 3/175:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/22$206
This Mytrip deal was found by Cheapflights users on 2/22. 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.
Tue 4/88:00 pmYYZ - ORD
1 stop19h 03mMultiple Airlines
Tue 4/158:45 amORD - YYZ
1 stop9h 45mMultiple Airlines
Deal found 2/22$211
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Sun 4/139:00 amYYZ - ORD
Nonstop2h 01mUnited Airlines
Sat 4/198:25 pmORD - YYZ
Nonstop1h 42mUnited Airlines
Deal found 2/22$221
This Air Canada deal was found by Cheapflights users on 2/21. 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.
Sat 4/1212:20 pmYYZ - ORD
Nonstop1h 55mAir Canada
Mon 4/219:05 pmORD - YYZ
Nonstop1h 53mAir Canada
Deal found 2/21$222
This Air Canada deal was found by Cheapflights users on 2/22. 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 4/107:25 amYTZ - ORD
1 stop5h 07mAir Canada
Sat 4/121:56 pmORD - YTZ
1 stop5h 41mAir Canada
Deal found 2/22$226
This Ticket deal was found by Cheapflights users on 2/22. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1511:10 amYTZ - MDW
Nonstop1h 50mAir Transat
Mon 3/175:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 2/22$227
This Trip.com deal was found by Cheapflights users on 2/22. 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.
Thu 4/109:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 4/245:35 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 2/22$229
This CheapTicketsDeal deal was found by Cheapflights users on 2/21. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/187:21 pmYYZ - MDW
1 stop20h 01mWestJet
Sun 4/2010:20 amMDW - YYZ
1 stop11h 54mWestJet
Deal found 2/21$244
This Delta deal was found by Cheapflights users on 2/22. 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 3/1510:20 amYYZ - ORD
1 stop3h 21mDelta
Tue 3/187:15 amORD - YYZ
1 stop5h 32mDelta
Deal found 2/22$246
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/306:00 amYYZ - MDW
1 stop7h 36mDelta
Fri 4/46:42 pmMDW - YYZ
1 stop2h 57mDelta
Deal found 2/21$246
This Booking.com deal was found by Cheapflights users on 2/22. 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.
Wed 4/91:10 pmYUL - ORD
Nonstop2h 40mAir Canada
Wed 4/1611:30 amORD - YUL
Nonstop2h 16mAir Canada
Deal found 2/22$257
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Sun 4/66:30 amYYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 4/64:45 pmORD - YYZ
1 stop4h 34mAmerican Airlines
Deal found 2/21$258

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 February 22, 2025.

Fly from

Ontario

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 3/15

11:10 am-12:00 pm

Nonstop1h 50m

Chicago Midway

Mon 3/17

5:35 pm-8:17 pm

Nonstop1h 42m

$206

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 4/8

8:00 pm-2:03 pm

1 stop19h 03m

Chicago O'Hare Intl

Tue 4/15

8:45 am-7:30 pm

1 stop9h 45m

$211

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 4/13

9:00 am-10:01 am

Nonstop2h 01m

Chicago O'Hare Intl

Sat 4/19

8:25 pm-11:07 pm

Nonstop1h 42m

$221

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/12

12:20 pm-1:15 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 4/21

9:05 pm-11:58 pm

Nonstop1h 53m

$222

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 4/8

8:00 pm-5:23 am

1 stop10h 23m

Chicago Midway

Wed 4/16

3:00 pm-11:54 pm

1 stop7h 54m

$225

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 4/10

7:25 am-11:32 am

1 stop5h 07m

Chicago O'Hare Intl

Sat 4/12

1:56 pm-8:37 pm

1 stop5h 41m

$226

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 3/15

11:10 am-12:00 pm

Nonstop1h 50m

Chicago Midway

Mon 3/17

5:35 pm-8:17 pm

Nonstop1h 42m

$227

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/10

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Thu 4/24

5:35 pm-8:17 pm

Nonstop1h 42m

$229

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 4/8

6:30 am-2:17 pm

1 stop8h 47m

Chicago Midway

Tue 4/15

7:00 pm-11:34 am

1 stop15h 34m

$245

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 3/15

10:20 am-12:41 pm

1 stop3h 21m

Chicago O'Hare Intl

Wed 3/19

7:15 am-1:47 pm

1 stop5h 32m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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, 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 February 22, 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 February 22, 2025.

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 (48 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 February 22, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta and Porter 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.
Alaska Airlines
8.0
Very good
9,702 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,702 reviews
Alaska Airlines
8.0
Very good
9,702 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,203 reviews
Alaska Airlines
8.0
Very good
9,702 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Porter Airlines
7.9
Good
277 reviews
Alaska Airlines
8.0
Very good
9,702 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Air Transat
7.8
Good
382 reviews
Alaska Airlines
8.0
Very good
9,702 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Austrian Airlines
7.5
Good
771 reviews
Alaska Airlines
8.0
Very good
9,702 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $131. Users have also found prices from $136 and $136 on United Airlines and Porter 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: Emirates (90%), Republic Airways (89%), ANA (84%).

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

    On average you can expect to pay $858 for a flight from Region of Ontario to Chicago. The cheapest flight overall is $129 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at $221.

  • 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
New Buffalo
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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$194Average$308FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$210Average$425FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$233Average$435FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$323FlexibilityNo cancel feeOn-time71%
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