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Cheap flights from Ontario to Chicago from C$ 178

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 21/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
5 Apr — 12 Apr1
1 adult

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 31 March 2025.

Round-trip from

C$ 286

One-way from

C$ 178

Popular in

December

Cheapest in

April

Average price

C$ 400

Good round-trip deal

C$ 276 or less

Good one-way deal

C$ 172 or less
Porter Airlines
  • Porter Airlines
  • 23/4-30/4
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Porter Airlines
  • Porter Airlines
  • 21/4
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Ontario to Chicago (CHI).
Search Deals
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 31 March 2025.

Wed 23/49:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 30/411:15 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 31/3C$ 286
Wed 14/56:35 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Wed 21/58:25 p.m.ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 31/3C$ 306
Thu 15/58:25 a.m.YTZ - ORD
1 stop7h 22mAir Canada
Thu 22/52:07 p.m.ORD - YTZ
1 stop6h 28mAir Canada
Deal found 30/3C$ 314
Mon 28/49:00 p.m.YYZ - ORD
Nonstop2h 06mUnited Airlines
Mon 5/512:00 p.m.ORD - YYZ
Nonstop1h 38mUnited Airlines
Deal found 31/3C$ 329
Mon 21/410:45 a.m.YUL - MDW
1 stop6h 55mPorter Airlines
Tue 29/45:35 p.m.MDW - YUL
1 stop4h 12mPorter Airlines
Deal found 29/3C$ 344
Wed 14/54:05 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Wed 21/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 30/3C$ 349
Wed 30/49:15 a.m.YUL - ORD
Nonstop2h 32mAir Canada
Sun 4/58:40 a.m.ORD - YUL
Nonstop2h 15mAir Canada
Deal found 31/3C$ 352
Sat 26/46:35 p.m.YYZ - ORD
Nonstop1h 55mLufthansa
Mon 28/49:05 p.m.ORD - YYZ
Nonstop1h 53mLufthansa
Deal found 31/3C$ 353
Thu 1/53:35 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Sun 4/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 30/3C$ 356
Tue 17/612:10 p.m.YYZ - ORD
1 stop5h 38mMultiple Airlines
Wed 18/62:16 p.m.ORD - YYZ
1 stop5h 48mMultiple Airlines
Deal found 31/3C$ 357
Thu 19/68:20 a.m.YUL - ORD
Nonstop2h 26mMultiple Airlines
Tue 24/62:16 p.m.ORD - YUL
1 stop6h 30mMultiple Airlines
Deal found 31/3C$ 359
Fri 25/42:30 p.m.YYZ - ORD
1 stop8h 53mDelta
Sun 27/46:35 a.m.ORD - YYZ
1 stop4h 24mDelta
Deal found 31/3C$ 370

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 629,999 searches. Data last updated 31 March 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

Wed 23/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

Chicago Midway

Wed 30/4

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

C$ 286

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 14/5

6:35 p.m.-7:30 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Wed 21/5

8:25 p.m.-11:07 p.m.

Nonstop1h 42m

C$ 306

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 15/5

8:25 a.m.-2:47 p.m.

1 stop7h 22m

Chicago O'Hare Intl

Thu 22/5

2:07 p.m.-9:35 p.m.

1 stop6h 28m

C$ 314

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 28/4

9:00 p.m.-10:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Mon 5/5

12:00 p.m.-2:38 p.m.

Nonstop1h 38m

C$ 329

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 21/4

10:45 a.m.-4:40 p.m.

1 stop6h 55m

Chicago Midway

Tue 29/4

5:35 p.m.-10:47 p.m.

1 stop4h 12m

C$ 344

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 14/5

4:05 p.m.-4:54 p.m.

Nonstop1h 49m

Chicago Midway

Wed 21/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 349

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 30/4

9:15 a.m.-10:47 a.m.

Nonstop2h 32m

Chicago O'Hare Intl

Sun 4/5

8:40 a.m.-11:55 a.m.

Nonstop2h 15m

C$ 352

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 26/4

6:35 p.m.-7:30 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Mon 28/4

9:05 p.m.-11:58 p.m.

Nonstop1h 53m

C$ 353

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/5

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Sun 4/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 356

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 17/6

12:10 p.m.-4:48 p.m.

1 stop5h 38m

Chicago O'Hare Intl

Wed 18/6

2:16 p.m.-9:04 p.m.

1 stop5h 48m

C$ 357

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/3

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, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 261). Flying from Region of Ontario to Chicago in March is currently the most expensive (average of C$ 355). 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 31 March 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 31 March 2025.

The most flights from CAON to CHI are scheduled on a Sunday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 31 March 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines and Air Transat from Ontario to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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
7,899 reviews
Check prices

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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
7,899 reviews
Check prices

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Aeromexico
7.5
Good
1,700 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
United Airlines
7.4
Good
8,614 reviews
Delta
8.0
Very good
7,899 reviews
Check prices

Food

7.3

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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?

    The cheapest airline one-way is Porter Airlines, with whom users have recently found tickets for as low as C$ 178. However, be on the lookout for offers from Air Canada and United Airlines, as they are both options that can get you from Region of Ontario to Chicago for a low price.

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

    When deciding which route to take from Region of Ontario to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Toronto Island - Chicago Midway as they are the most popular.

  • What are the most reliable airlines from Region of Ontario to Chicago?

    No one likes to see their flight delayed. When booking a flight from Region of Ontario to Chicago consider choosing Copa Airlines (88%), Emirates (87%) or ANA (86%) as they are the most reliable in getting you off to your destination on time.

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

    On average you can expect to pay C$ 2,590 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 199 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 329.

  • 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, January is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 261). Flying from Region of Ontario to Chicago in March is currently the most expensive (average of C$ 355). 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

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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
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
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Pearson Intl to St. Louis flights
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Edmonton to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
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Calgary to St. Louis flights
Pierre Elliott Trudeau Intl to St. Louis flights
Halifax to Midway flights
Pearson Intl to Moline flights
St. John's to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Regina to O'Hare Intl flights
Pearson Intl to Peoria flights
St John to O'Hare Intl flights
Victoria to Midway flights
Victoria to O'Hare Intl flights
Saskatoon to Midway flights
Ottawa to St. Louis flights
Saskatoon to O'Hare Intl flights
Comox to O'Hare Intl flights
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Edmonton to St. Louis flights
Victoria to St. Louis flights
Pearson Intl to Quincy flights
London to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Kelowna to Midway flights
Fort McMurray to O'Hare Intl flights
Ottawa to Champaign flights
Pearson Intl to Bloomington flights
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Top 5 airlines flying from Ontario to Chicago

Discover the top 5 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 629,999 searches. Data last updated 31 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 270AverageC$ 430FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 313AverageC$ 536FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 331AverageC$ 541FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 343AverageC$ 649FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 445AverageC$ 654FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Ontario to Chicago?

When you search for this flight from Ontario to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Ontario to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Ontario.

Can Cheapflights find flights from Ontario to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Ontario shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Ontario to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Ontario to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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