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Cheap flights from Ontario to Chicago from C$ 160

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 24/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

C$ 271

One-way from

C$ 160

Popular in

December

Cheapest in

July

Average price

C$ 351

Good round-trip deal

C$ 241 or less

Good one-way deal

C$ 211 or less
20/10-23/10
  • 20/10-23/10
  • 2 total stops
  • 15h 58m total
  • Ontario to Chicago
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WestJet
  • WestJet
  • 24/10
  • 1 total stop
  • 11h 43m total
  • Ontario to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 42 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 16 September 2025.

Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 23/1012:53 p.m.ORD - YYZ
1 stop7h 14mMultiple Airlines
Deal found 14/9C$ 271
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Wed 22/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 15/9C$ 275
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Thu 23/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 15/9C$ 279
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 30/107:06 p.m.ORD - YYZ
1 stop25h 01mMultiple Airlines
Deal found 14/9C$ 282
Mon 3/114:00 p.m.YYZ - ORD
1 stop7h 39mMultiple Airlines
Thu 6/116:06 p.m.ORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 15/9C$ 283
Mon 13/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 23/107:43 p.m.ORD - YYZ
1 stop17h 22mMultiple Airlines
Deal found 15/9C$ 285
Thu 23/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Mon 27/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 14/9C$ 286
Sun 19/104:00 p.m.YYZ - ORD
1 stop24h 49mMultiple Airlines
Fri 24/105:05 a.m.ORD - YYZ
1 stop8h 00mMultiple Airlines
Deal found 14/9C$ 290
Mon 13/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Thu 6/116:06 p.m.ORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 15/9C$ 291
Mon 20/104:00 p.m.YYZ - ORD
1 stop8h 44mMultiple Airlines
Sun 2/116:06 p.m.ORD - YYZ
1 stop26h 01mMultiple Airlines
Deal found 14/9C$ 296
Fri 24/106:00 a.m.YKF - ORD
1 stop11h 43mWestJet
Sun 26/102:20 p.m.ORD - YKF
1 stop14h 08mWestJet
Deal found 13/9C$ 311
Tue 14/107:30 p.m.YTZ - MDW
1 stop4h 55mMultiple Airlines
Wed 22/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 15/9C$ 323

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 16 September 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

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Thu 23/10

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Mon 27/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 286

TorontoChicago

YKF - ORD

YKFORD

Toronto Region of Waterloo Intl

Fri 24/10

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Sun 26/10

2:20 p.m.-5:28 a.m.

1 stop14h 08m

C$ 311

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Wed 22/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 323

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Thu 23/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 323

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 24/10

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

1 stop4h 14m

Chicago Midway

Sun 26/10

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 329

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/10

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

1 stop4h 14m

Chicago Midway

Sun 19/10

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

1 stop3h 55m

C$ 329

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 13/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Sat 25/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 332

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

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$ 348). 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 16 September 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 16 September 2025.

The most flights from CAON to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).

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.

  • How long is the flight from Region of Ontario to Chicago?

    For as low as C$ 359, WestJet can have you in Chicago from Region of Ontario in 3h. Region of Ontario and Chicago are separated by a distance of 1199 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines to fly from Region of Ontario to Chicago one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 160. 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 Pearson Intl - 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 EVA Air (88%), Egyptair (85%) or Copa Airlines (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$ 1,703 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 240 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 271.

  • 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$ 348). 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
Pearson Intl to Midway flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Vancouver Intl to Midway flights
Calgary to O'Hare Intl flights
Québec City to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Pearson Intl to St. Louis flights
Ottawa to O'Hare Intl flights
Halifax to O'Hare Intl flights
Calgary to Midway flights
Winnipeg to O'Hare Intl flights
Québec City to Midway flights
Edmonton to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Ottawa to Midway flights
Halifax to Midway flights
Victoria to O'Hare Intl flights
Edmonton to Midway flights
Vancouver Intl to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Calgary to St. Louis flights
Saskatoon to O'Hare Intl flights
Edmonton to St. Louis flights
Kelowna to O'Hare Intl flights
London to O'Hare Intl flights
Kelowna to Midway flights
Victoria to Midway flights
Hamilton to O'Hare Intl flights
Ottawa to St. Louis flights
Pearson Intl to Peoria flights
Saskatoon to Midway flights
Regina to O'Hare Intl flights
Halifax to St. Louis flights
Pearson Intl to Bloomington flights
St. John's to O'Hare Intl flights
Québec City to St. Louis flights
Kingston to O'Hare Intl flights
St John to O'Hare Intl flights
Sudbury to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Moncton to O'Hare Intl flights

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 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 196AverageC$ 357FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 264AverageC$ 498FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 267AverageC$ 496FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 278AverageC$ 552FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 382AverageC$ 630FlexibilityNo 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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