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Cheap flights from Ontario to Chicago from C$ 151

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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
20 Mar — 27 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Ontario to Chicago

Enter your travel dates to find the best prices.

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 18 February 2026.

Thu 16/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Sun 19/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 14/2C$ 228
Sat 18/48:55 a.m.
YUL
-
MDW
1 stop3h 55m
Porter Airlines
Mon 20/44:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Deal found 14/2C$ 231
Thu 19/31:10 p.m.
YUL
-
ORD
Nonstop2h 45m
Air Canada
Mon 23/37:15 a.m.
ORD
-
YUL
Nonstop2h 05m
Air Canada
Deal found 16/2C$ 240
Fri 10/411:45 a.m.
YUL
-
MDW
1 stop4h 35m
Porter Airlines
Sun 12/44:05 p.m.
MDW
-
YUL
1 stop5h 40m
Porter Airlines
Deal found 16/2C$ 242
Thu 26/31:10 p.m.
YUL
-
ORD
Nonstop2h 45m
Air Canada
Sun 29/33:45 p.m.
ORD
-
YUL
Nonstop2h 10m
Air Canada
Deal found 15/2C$ 244
Fri 1/56:30 p.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Thu 7/58:45 a.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 17/2C$ 252
Thu 26/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 29/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/2C$ 259
Fri 17/46:30 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 19/49:50 a.m.
ORD
-
YYZ
Nonstop1h 36m
Air Canada
Deal found 17/2C$ 261
Thu 28/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 1/610:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 15/2C$ 261
Mon 13/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Thu 16/411:00 a.m.
MDW
-
YUL
1 stop7h 15m
Porter Airlines
Deal found 18/2C$ 261
Thu 21/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 25/55:35 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 14/2C$ 262
Mon 11/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Fri 15/510:25 a.m.
MDW
-
YUL
1 stop8h 45m
Porter Airlines
Deal found 14/2C$ 263

Find flight deals from Ontario to Chicago

Keep the following information in mind while searching for Ontario to Chicago flight deals. Data was last updated 18 February 2026.

Round-trip from

C$ 228

One-way from

C$ 151

Popular in

February

Cheapest in

July

Average price

C$ 388

Good round-trip deal

C$ 262 or less

Good one-way deal

C$ 237 or less
Porter Airlines
  • Porter Airlines
  • 16/4-19/4
  • 2 total stops
  • 10h 05m total
  • Ontario to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 11/3
  • 1 total stop
  • 4h 15m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
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).
Search Deals

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 18 February 2026.
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

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 16/4

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 19/4

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 228

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 18/4

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Mon 20/4

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

1 stop5h 30m

C$ 231

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Mon 20/4

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 242

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/4

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Fri 17/4

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 242

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 1/5

6:30 p.m.-8:08 p.m.

Nonstop2h 38m

Chicago O'Hare Intl

Thu 7/5

8:45 a.m.-12:00 p.m.

Nonstop2h 15m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 29/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

Chicago Midway

Wed 3/6

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 21/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 25/5

5:35 p.m.-8:15 p.m.

Nonstop1h 40m

C$ 262

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 22/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

Chicago Midway

Sun 24/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 262

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 21/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

Chicago Midway

Sun 24/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 262

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/6

6:15 a.m.-10:18 a.m.

1 stop5h 03m

Chicago O'Hare Intl

Mon 15/6

9:55 a.m.-12:35 p.m.

Nonstop1h 40m

C$ 272

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/2

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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, April is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 109). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of C$ 251). 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 18 February 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 19% on flights from Region of Ontario to Chicago by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Region of Ontario to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Ontario to Chicago. Price data was last updated on 7 February 2026.

Travelers seeking maximum savings on their Region of Ontario to Chicago flight should consider departing on Monday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 18 February 2026.

The most flights from CAON to CHI are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 on average).

How much does it cost to fly round-trip from Region of Ontario to Chicago?

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$ 285, Porter Airlines can have you in Chicago from Region of Ontario in 2h 03m. Region of Ontario and Chicago are separated by a distance of 702 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 Porter Airlines, with whom users have recently found tickets for as low as C$ 122. However, be on the lookout for offers from United 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 Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl, Toronto Pearson 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 Emirates (100%), Copa Airlines (87%) or Qatar Airways (80%) 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$ 1,848 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 223 while the most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) is currently priced at C$ 273.

  • 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, April is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 109). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of C$ 251). 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.
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Calgary to O'Hare Intl flights
Toronto Island to Midway flights
Vancouver Intl to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Toronto Island to O'Hare Intl flights
Pearson Intl to St. Louis flights
Vancouver Intl to St. Louis flights
Halifax to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Calgary to Midway flights
Ottawa to O'Hare Intl flights
Edmonton to Midway flights
Québec City to O'Hare Intl flights
Halifax to Midway flights
Winnipeg to O'Hare Intl flights
Ottawa to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Victoria to O'Hare Intl flights
Halifax to St. Louis flights
Hamilton to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Québec City to Midway flights
St. John's to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Saskatoon to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Vancouver Intl to Peoria flights
Regina to O'Hare Intl flights
St John to O'Hare Intl flights
Calgary to St. Louis flights
Victoria to Midway flights
Ottawa to St. Louis flights
Kelowna to Midway flights
Pearson Intl to Champaign flights
Pearson Intl to Moline flights
Charlottetown to St. Louis flights
Sudbury to O'Hare Intl flights
Saskatoon to St. Louis flights
Moncton to O'Hare Intl flights
Nanaimo to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
London to O'Hare Intl flights
Victoria to St. Louis 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 18 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 357FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 221AverageC$ 409FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 244AverageC$ 464FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 259AverageC$ 509FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 364AverageC$ 469FlexibilityNo 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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