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Cheap flights from Ontario to Chicago from C$ 224

YYZ — CHI
5 Nov — 12 Nov1
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

Sat 24/102:00 p.m. -
Nonstop1h 55m
Fri 30/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 312
Sat 24/1012:15 p.m. -
Nonstop2h 10m
Fri 30/101:55 p.m. -
Nonstop1h 47m
Deal found 5/10C$ 324
Sat 31/107:44 p.m. -
1 stop13h 45m
Sun 1/1111:05 a.m. -
Nonstop1h 58m
Deal found 5/10C$ 329
Sat 5/128:35 a.m. -
Nonstop2h 09m
Sat 5/126:15 p.m. -
1 stop4h 37m
Deal found 4/10C$ 331
Sat 21/1110:00 a.m. -
1 stop5h 40m
Sat 21/119:21 p.m. -
Nonstop1h 38m
Deal found 4/10C$ 349
Fri 30/107:26 p.m. -
Nonstop2h 22m
Sat 31/106:59 a.m. -
1 stop5h 44m
Deal found 1/10C$ 358
Wed 21/101:45 p.m. -
Nonstop1h 50m
Sat 24/1011:45 a.m. -
Nonstop1h 40m
Deal found 4/10C$ 359
Thu 5/118:20 a.m. -
Nonstop2h 03m
Sat 7/1110:15 a.m. -
Nonstop1h 37m
Deal found 5/10C$ 372
Thu 19/116:45 a.m. -
1 stop5h 22m
Thu 26/111:55 p.m. -
Nonstop1h 47m
Deal found 5/10C$ 372
Sat 14/114:35 p.m. -
Nonstop2h 05m
Fri 20/116:20 p.m. -
Nonstop1h 45m
Deal found 5/10C$ 375
Sat 28/1110:35 a.m. -
Nonstop2h 05m
Tue 1/126:20 p.m. -
Nonstop1h 46m
Deal found 1/10C$ 376
Sat 31/1010:35 a.m. -
Nonstop2h 05m
Tue 3/1112:20 p.m. -
Nonstop1h 46m
Deal found 1/10C$ 378

Find flight deals from Ontario to Chicago

Round-trip from

C$ 312

One-way from

C$ 224

Popular in

October

Cheapest in

February

Average price

C$ 428

Good round-trip deal

C$ 329 or less

Good one-way deal

C$ 186 or less
Air Canada
  • Air Canada
  • 24/10-30/10
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
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Air Canada
  • Air Canada
  • 28/10-31/12
  • Nonstop
  • 2h 13m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 8 potential increase over avg. RT price).
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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 October 2026
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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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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Ontario to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 22/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 240

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 22/10

12:15 p.m.-1:25 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 245

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 5/12

3:35 p.m.-4:44 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 254

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 14/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 255

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 6/12

6:00 a.m.-1:56 p.m.

1 stop8h 56m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 28/10

7:43 a.m.-3:14 p.m.

1 stop8h 31m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 19/11

9:45 a.m.-1:59 p.m.

1 stop5h 14m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Tue 24/11

2:20 p.m.-6:04 p.m.

1 stop4h 44m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 6/11

2:57 p.m.-12:01 a.m.

1 stop10h 04m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 278

TorontoChicago

YYZ Toronto Pearson Intl - MDW Chicago Midway

YYZMDW

Toronto Pearson Intl

Sat 14/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 278

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

Showing 1-10 of 60 resultsSorted by cheapest first
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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

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$ 366). Flying from Region of Ontario to Chicago in December is currently the most expensive (average of C$ 472). 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?

Unlike in the afternoon, 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 at noon.

Weekly flight availability from Region of Ontario to Chicago

The most flights from CAON to CHI are scheduled on a Sunday (69 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (42 on average).

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

Airfare is below average for this route at the moment.
Region of Ontario to Chicago flights typically cost between C$ 332 and C$ 572 in October.
The cheapest round-trip price found within the last 5 days was C$ 312 on Air Canada (24 Oct-30 Oct).

How far ahead should I book a flight from Region of Ontario to Chicago?

The best time to book flights from Region of Ontario to Chicago is 87 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

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

Related info for your journey

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

    For as low as C$ 411, Porter Airlines can have you in Chicago from Region of Ontario in 2h 05m. Region of Ontario and Chicago are separated by a distance of 716 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$ 155. 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 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 Sun Country Air (100%), Copa Airlines (86%) or Egyptair (76%) 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$ 1,463 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 252 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 426.

  • 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$ 366). Flying from Region of Ontario to Chicago in December is currently the most expensive (average of C$ 472). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Ontario to Chicago

Pearson Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to St. Louis flights
Calgary to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Winnipeg to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Vancouver Intl to Midway flights
Québec City to O'Hare Intl flights
Calgary to Midway flights
Halifax to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Edmonton to O'Hare Intl flights
Ottawa to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Québec City to Midway flights
Vancouver Intl to St. Louis flights
Halifax to Midway flights
Edmonton to Midway flights
Saskatoon to O'Hare Intl flights
Ottawa to St. Louis flights
Victoria to O'Hare Intl flights
Regina to O'Hare Intl flights
Pearson Intl to Moline flights
Fort McMurray to O'Hare Intl flights
Pearson Intl to Bloomington flights
Calgary to St. Louis flights
Edmonton to St. Louis flights
Victoria to Midway flights
Saskatoon to Midway flights
Saskatoon to St. Louis flights
Moncton to O'Hare Intl flights
Vancouver Intl to Peoria flights
Pearson Intl to Champaign flights
Sudbury to O'Hare Intl flights
Victoria to St. Louis flights
London to O'Hare Intl flights
Grande Prairie to Midway flights
Québec City to St. Louis flights
St. John's to O'Hare Intl flights
Charlottetown to St. Louis flights
Deer Lake to O'Hare Intl flights

Top 5 airlines flying from Ontario to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 138AverageC$ 613FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 255AverageC$ 438FlexibilityNo cancel feeOn-time52%
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American AirlinesCheapestC$ 268AverageC$ 448FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 302AverageC$ 617FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 362AverageC$ 473FlexibilityNo cancel feeOn-time60%
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Fly with Cheapflights

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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