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Cheap flights from Canada to Chicago

YYZ — CHI
22 Mar — 29 Mar1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated 20 February 2026.

Round-trip from

C$ 204

One-way from

C$ 136

Popular in

February

Cheapest in

July

Average price

C$ 392

Good round-trip deal

C$ 263 or less

Good one-way deal

C$ 179 or less
WestJet
  • WestJet
  • 20/5-27/5
  • Nonstop
  • 7h 35m total
  • Canada to Chicago
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WestJet
  • WestJet
  • 20/5
  • Nonstop
  • 3h 40m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 37 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 February 2026
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Price to beat on a round-trip flight from Canada to Chicago (CHI).
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Price to beat on a one-way flight from Canada to Chicago (CHI).
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Cheapflights Insights

Everything you need to know about your flight from Canada to Chicago

What is the cheapest month to book a flight from Canada to Chicago?

Currently, April is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 110). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 186). 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 CA to CHI?

Find hourly flight availability from Canada 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 20 February 2026.

It’s typically best to fly out from Canada to Chicago in the evening. Doing so could potentially save you 27% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Canada to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Canada to Chicago. Price data was last updated on 17 February 2026.

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 20 February 2026.
Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andAmerican Airlines from Canada to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
419 reviews
Check prices

Entertainment

6.9

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Porter Airlines
8.0
Very good
419 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Entertainment

6.9

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
United Airlines
7.4
Good
9,325 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Entertainment

6.9

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
American Airlines
7.2
Good
11,321 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Entertainment

6.9

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
WestJet
7.2
Good
3,270 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Entertainment

6.9

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Air Canada
7.1
Good
10,732 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Entertainment

6.9

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

Related info for your journey

Find useful and relevant information for your journey from Canada 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 Canada to Chicago?

    A quick flight from Canada to Chicago can take about 1h 50m. Porter Airlines provides one of the quickest options available for as low as C$ 262. Canada 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 Canada to Chicago one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 116. Porter Airlines flights start at C$ 122 while deals on United Airlines start at C$ 160 one-way.

  • What are the most popular routes from Canada to Chicago?

    When deciding which route to take from Canada to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Vancouver Intl - Chicago O'Hare Intl as they are the most popular.

  • What are the most reliable airlines from Canada to Chicago?

    Before booking your flight to Chicago from Canada, check out the most reliable airlines to get you to your destination on time: Emirates (100%), Copa Airlines (87%), Qatar Airways( 80%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 228. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 262 on average, our data indicates C$ 1,783 when flying from Canada to Chicago.

  • Can I find deals for flights from Canada to Chicago that include hotel bookings?

    Yes. In addition to deals on Canada to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Chicago.

  • Can I find deals for business class flights from Canada to Chicago?

    Yes. Cheapflights offers flight deals from Canada 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 Canada to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 110). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 186). 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 Canada to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Canada to Chicago

Discover the top 7 airlines that operate flights from Canada 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 20 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 386FlexibilityNo cancel feeOn-time52%
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Air CanadaCheapestC$ 121AverageC$ 489FlexibilityNo cancel feeOn-time67%
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DeltaCheapestC$ 145AverageC$ 365FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapestC$ 167AverageC$ 470FlexibilityNo cancel feeOn-time69%
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American AirlinesCheapestC$ 169AverageC$ 379FlexibilityNo cancel feeOn-time71%
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WestJetCheapestC$ 176AverageC$ 354FlexibilityNo cancel feeOn-time60%
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Alaska AirlinesCheapestC$ 383AverageC$ 495FlexibilityNo cancel feeOn-time75%
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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 Canada to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Canada to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Canada to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Canada to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Canada to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Canada 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 Canada to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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