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Cheap flights from Ontario to Chicago from C$ 165

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 18/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
5 May — 12 May1
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 30 April 2025.

Round-trip from

C$ 244

One-way from

C$ 165

Popular in

December

Cheapest in

March

Average price

C$ 350

Good round-trip deal

C$ 264 or less

Good one-way deal

C$ 151 or less
Porter Airlines
  • Porter Airlines
  • 22/5-26/5
  • Nonstop
  • 3h 31m total
  • Ontario to Chicago
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American Airlines
  • American Airlines
  • 18/6
  • Nonstop
  • 1h 55m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 27 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 April 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 30 April 2025.

Thu 22/53:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 26/59:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/4C$ 244
Fri 13/67:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Fri 20/65:50 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 29/4C$ 248
Fri 6/67:25 a.m.YTZ - ORD
1 stop4h 59mAir Canada
Sun 8/62:07 p.m.ORD - YTZ
1 stop6h 28mAir Canada
Deal found 28/4C$ 256
Sun 1/64:05 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 2/65:50 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 29/4C$ 263
Fri 30/52:10 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Sat 31/58:25 p.m.ORD - YYZ
Nonstop1h 42mAir Canada
Deal found 29/4C$ 266
Thu 29/51:15 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Thu 5/612:48 p.m.ORD - YYZ
1 stop4h 56mAmerican Airlines
Deal found 29/4C$ 323
Fri 23/56:15 a.m.YUL - ORD
Nonstop2h 44mAir Canada
Mon 26/57:19 a.m.ORD - YUL
Nonstop2h 21mAir Canada
Deal found 28/4C$ 347
Fri 23/56:15 a.m.YUL - ORD
Nonstop2h 44mUnited Airlines
Tue 27/52:07 p.m.ORD - YUL
Nonstop2h 19mUnited Airlines
Deal found 29/4C$ 349
Thu 12/62:10 p.m.YYZ - ORD
Nonstop1h 55mMultiple Airlines
Wed 18/62:16 p.m.ORD - YYZ
1 stop5h 48mMultiple Airlines
Deal found 29/4C$ 354
Tue 27/51:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Tue 3/65:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 29/4C$ 354
Wed 21/512:30 p.m.YYZ - MDW
1 stop6h 15mDelta
Wed 28/56:25 p.m.MDW - YYZ
1 stop3h 33mDelta
Deal found 29/4C$ 360
Wed 21/59:49 a.m.YYZ - ORD
1 stop3h 52mDelta
Fri 30/57:10 a.m.ORD - YYZ
1 stop6h 50mDelta
Deal found 29/4C$ 365

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 30 April 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

Thu 22/5

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

Nonstop1h 49m

Chicago Midway

Mon 26/5

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

Nonstop1h 42m

C$ 244

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 13/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Fri 20/6

5:50 p.m.-8:32 p.m.

Nonstop1h 42m

C$ 248

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 6/6

7:25 a.m.-11:24 a.m.

1 stop4h 59m

Chicago O'Hare Intl

Sun 8/6

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

1 stop6h 28m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/6

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

Nonstop1h 49m

Chicago Midway

Mon 2/6

5:50 p.m.-8:32 p.m.

Nonstop1h 42m

C$ 263

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 30/5

2:10 p.m.-3:05 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Sat 31/5

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

Nonstop1h 42m

C$ 266

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 29/5

1:15 p.m.-2:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Thu 5/6

12:48 p.m.-6:44 p.m.

1 stop4h 56m

C$ 323

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 23/5

6:15 a.m.-7:59 a.m.

Nonstop2h 44m

Chicago O'Hare Intl

Mon 26/5

7:19 a.m.-10:40 a.m.

Nonstop2h 21m

C$ 347

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 23/5

6:15 a.m.-7:59 a.m.

Nonstop2h 44m

Chicago O'Hare Intl

Tue 27/5

2:07 p.m.-5:26 p.m.

Nonstop2h 19m

C$ 349

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/6

2:45 p.m.-3:50 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Tue 17/6

2:16 p.m.-9:07 p.m.

1 stop5h 51m

C$ 354

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 27/5

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Tue 3/6

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 354

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

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$ 353). 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 30 April 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 30 April 2025.

The most flights from CAON to CHI are scheduled on a Wednesday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 30 April 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta and KLM 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.
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,936 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
KLM
7.8
Good
1,333 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Aeromexico
7.5
Good
1,698 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Overall

8.0

Crew

8.8

Food

7.6

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 American Airlines, with whom users have recently found tickets for as low as C$ 165. However, be on the lookout for offers from Porter Airlines and Air Canada, 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 (90%), Egyptair (89%) or ANA (85%) 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$ 1,265 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 183 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 266.

  • 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$ 353). 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.
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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 30 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 260AverageC$ 406FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 301AverageC$ 520FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 301AverageC$ 489FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 329AverageC$ 605FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 429AverageC$ 631FlexibilityNo 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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