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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 20/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
22 Jan — 29 Jan1
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 23 December 2025.

Sun 28/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 30/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 20/12C$ 410
Wed 31/123:15 p.m.YYZ - ORD
1 stop7h 52mMultiple Airlines
Tue 10/25:32 p.m.ORD - YYZ
1 stop28h 48mMultiple Airlines
Deal found 22/12C$ 460
Wed 31/123:40 p.m.YYZ - ORD
1 stop24h 22mMultiple Airlines
Sun 8/27:21 p.m.ORD - YYZ
1 stop18h 32mMultiple Airlines
Deal found 22/12C$ 482
Tue 30/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 8/211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/12C$ 485
Tue 30/127:45 p.m.YYZ - ORD
1 stop27h 22mMultiple Airlines
Sun 8/27:21 p.m.ORD - YYZ
1 stop18h 32mMultiple Airlines
Deal found 22/12C$ 505
Tue 30/126:45 p.m.YYZ - ORD
Nonstop2h 00mAir Canada
Sun 8/26:28 p.m.ORD - YYZ
Nonstop1h 53mAir Canada
Deal found 22/12C$ 533
Sun 28/125:15 p.m.YYZ - ORD
1 stop4h 21mMultiple Airlines
Fri 30/17:21 p.m.ORD - YYZ
2 stops23h 50mMultiple Airlines
Deal found 20/12C$ 537
Sun 28/125:15 p.m.YYZ - ORD
1 stop20h 39mWestJet
Fri 30/16:15 a.m.ORD - YYZ
1 stop8h 44mWestJet
Deal found 20/12C$ 542
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 4/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 22/12C$ 542
Sun 28/125:15 p.m.YYZ - MDW
1 stop16h 34mWestJet
Fri 30/19:50 a.m.MDW - YYZ
1 stop5h 09mWestJet
Deal found 20/12C$ 542
Mon 29/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Sun 8/22:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 22/12C$ 544
Tue 30/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 4/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/12C$ 547

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 23 December 2025.

Round-trip from

C$ 248

One-way from

C$ 160

Popular in

December

Cheapest in

July

Average price

C$ 447

Good round-trip deal

C$ 253 or less

Good one-way deal

C$ 176 or less
Air Transat
  • Air Transat
  • 5/2-8/2
  • Nonstop
  • 3h 32m total
  • Ontario to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 20/1
  • Nonstop
  • 1h 50m total
  • Ontario to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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).
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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 23 December 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 19/2

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

Nonstop1h 50m

Chicago Midway

Tue 24/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 252

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 22/1

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Thu 29/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 18/1

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

Nonstop1h 50m

Chicago Midway

Sun 25/1

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 9/2

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

Nonstop1h 50m

Chicago Midway

Tue 10/2

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

Nonstop1h 42m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 15/1

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

Chicago Midway

Mon 19/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

C$ 259

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/2

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

1 stop4h 20m

Chicago Midway

Sun 15/2

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

1 stop5h 30m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 24/1

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Sat 31/1

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 266

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/2

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

1 stop4h 20m

Chicago Midway

Sat 21/2

12:45 p.m.-6:45 p.m.

1 stop5h 00m

C$ 270

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/2

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

1 stop4h 20m

Chicago Midway

Sat 21/2

12:45 p.m.-6:45 p.m.

1 stop5h 00m

C$ 270

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/2

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

1 stop4h 20m

Chicago Midway

Mon 23/2

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

1 stop4h 30m

C$ 270

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/12

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, April is the cheapest month in which you can book a flight from Region of Ontario to Chicago (average of C$ 113). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of C$ 253). 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 23 December 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 17% 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 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. 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 23 December 2025.

The most flights from CAON to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (33 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$ 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 Porter Airlines, with whom users have recently found tickets for as low as C$ 123. 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 EVA Air (83%), Japan Airlines (80%) or Egyptair (78%) 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$ 1,750 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 145 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 256.

  • 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$ 113). Flying from Region of Ontario to Chicago in February is currently the most expensive (average of C$ 253). 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
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to Midway flights
Toronto Island to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Ottawa to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Calgary to O'Hare Intl flights
Vancouver Intl to Midway flights
Pearson Intl to St. Louis flights
Toronto Island to O'Hare Intl flights
Ottawa to Midway flights
Halifax to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Vancouver Intl to St. Louis flights
Halifax to Midway flights
Calgary to Midway flights
Edmonton to O'Hare Intl flights
Québec City to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
London to O'Hare Intl flights
Victoria to O'Hare Intl flights
Edmonton to St. Louis flights
Ottawa to St. Louis flights
Pearson Intl to Peoria flights
Vancouver Intl to Peoria flights
Edmonton to Midway flights
Québec City to Midway flights
Halifax to St. Louis flights
Kelowna to Midway flights
Grande Prairie to Midway flights
Sudbury to O'Hare Intl flights
Victoria to St. Louis flights
Moncton to O'Hare Intl flights
Victoria to Midway flights
Kelowna to O'Hare Intl flights
Saskatoon to Midway flights
Hamilton to O'Hare Intl flights
Pearson Intl to Moline flights
Fort McMurray to O'Hare Intl flights
Calgary to St. Louis flights
St. John's to O'Hare Intl flights
Halifax to Peoria flights
Region of Waterloo Intl to O'Hare Intl flights
Saskatoon to St. Louis flights
Regina 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 23 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 195AverageC$ 353FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 256AverageC$ 467FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 259AverageC$ 421FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 263AverageC$ 538FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 367AverageC$ 491FlexibilityNo 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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