Find flights
Deals
When to book
FAQs

Cheap flights from Ontario to Chicago from C$ 142

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
18 Dec — 25 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 November 2025.

Mon 22/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/11C$ 255
Tue 9/121:47 p.m.YYZ - ORD
1 stop5h 36mAmerican Airlines
Fri 12/125:00 a.m.ORD - YYZ
1 stop5h 12mAmerican Airlines
Deal found 18/11C$ 257
Mon 29/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/11C$ 259
Tue 23/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/11C$ 265
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Mon 8/126:04 a.m.ORD - YYZ
1 stop4h 52mAmerican Airlines
Deal found 17/11C$ 266
Wed 31/126:50 a.m.YYZ - ORD
Nonstop2h 13mLufthansa
Wed 7/19:15 p.m.ORD - YYZ
Nonstop1h 44mLufthansa
Deal found 15/11C$ 273
Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/11C$ 275
Sun 14/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 21/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 16/11C$ 276
Mon 8/124:13 p.m.YYZ - ORD
1 stop7h 41mAmerican Airlines
Thu 11/129:39 a.m.ORD - YYZ
Nonstop1h 51mAmerican Airlines
Deal found 16/11C$ 278
Wed 10/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Wed 10/121:16 p.m.ORD - YYZ
Nonstop1h 47mAmerican Airlines
Deal found 17/11C$ 279
Sun 7/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 13/1212:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/11C$ 279
Tue 2/129:15 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Fri 5/124:15 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 16/11C$ 282

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 18 November 2025.

Round-trip from

C$ 251

One-way from

C$ 142

Popular in

December

Cheapest in

July

Average price

C$ 394

Good round-trip deal

C$ 346 or less

Good one-way deal

C$ 197 or less
Porter Airlines
  • Porter Airlines
  • 2/12-5/12
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
Search Deals
11/1
  • 11/1
  • 3 total stops
  • 29h 34m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 52 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 November 2025
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 November 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

Sat 27/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 5/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 22/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 5/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 255

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 5/4

8:55 a.m.-9:55 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Fri 10/4

9:05 a.m.-11:50 a.m.

Nonstop1h 45m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 1/2

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Thu 5/2

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 15/1

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

Nonstop2h 06m

Chicago O'Hare Intl

Sat 24/1

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 29/1

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

Nonstop2h 06m

Chicago O'Hare Intl

Mon 16/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 6/4

1:00 p.m.-2:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Mon 13/4

5:57 p.m.-8:44 p.m.

Nonstop1h 47m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 5/4

8:55 a.m.-9:55 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 12/4

7:10 a.m.-10:04 a.m.

Nonstop1h 54m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/4

2:45 p.m.-3:48 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Fri 10/4

9:05 a.m.-11:50 a.m.

Nonstop1h 45m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 29/12

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 5/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 259

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/11

Showing 1-10 of 60 results
1
2
3
...
6

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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 116). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of C$ 266). 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 November 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 20% on flights from Region of Ontario to Chicago by exploring options for tickets in the evening.

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 16 December 2024.

Travelers seeking maximum savings on their Region of Ontario to Chicago flight should consider departing on Sunday mornings when fares are most often at their lowest. Sunday at noon 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 November 2025.

The most flights from CAON to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (51 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$ 255, Porter Airlines can have you in Chicago from Region of Ontario in 1h 50m. Region of Ontario and Chicago are separated by a distance of 711 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 Air Canada, with whom users have recently found tickets for as low as C$ 164. However, be on the lookout for offers from Porter Airlines 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 EVA Air (94%), Egyptair (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$ 2,092 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 220 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 215.

  • 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, June is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 116). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of C$ 266). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Vancouver Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Calgary to O'Hare Intl flights
Ottawa to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Winnipeg to O'Hare Intl flights
Pearson Intl to St. Louis flights
Halifax to O'Hare Intl flights
Calgary to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Halifax to Midway flights
Québec City to O'Hare Intl flights
Vancouver Intl to St. Louis flights
Edmonton to O'Hare Intl flights
Ottawa to Midway flights
Saskatoon to O'Hare Intl flights
Edmonton to Midway flights
Québec City to Midway flights
Vancouver Intl to Peoria flights
Saskatoon to Midway flights
Calgary to St. Louis flights
Regina to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Victoria to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Pearson Intl to Peoria flights
Halifax to St. Louis flights
Pearson Intl to Moline flights
London to O'Hare Intl flights
Ottawa to St. Louis flights
Fort McMurray to O'Hare Intl flights
Kelowna to Midway flights
Victoria to Midway flights
Saskatoon to St. Louis flights
St. John's to O'Hare Intl flights
Halifax to Peoria flights
Québec City to St. Louis flights
Edmonton to St. Louis flights
Victoria to St. Louis flights
Pearson Intl to Champaign flights
Pearson Intl to Bloomington flights
St John to O'Hare Intl flights
Sudbury 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 18 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 198AverageC$ 355FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
American AirlinesCheapestC$ 264AverageC$ 454FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 265AverageC$ 471FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 283AverageC$ 551FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 374AverageC$ 600FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.