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Cheap flights from Canada to Chicago from C$ 136

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
25 Feb — 4 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Canada to Chicago
Explore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 26 January 2026.

Mon 27/412:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 1/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 25/1C$ 247
Wed 25/36:25 p.m.
YUL
-
ORD
Nonstop2h 45m
Air Canada
Mon 30/312:50 p.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 26/1C$ 249
Tue 31/36:00 a.m.
YYC
-
ORD
1 stop12h 54m
United Airlines
Wed 8/410:49 a.m.
ORD
-
YYC
1 stop11h 59m
United Airlines
Deal found 25/1C$ 255
Fri 17/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 25/1C$ 255
Thu 19/22:15 p.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Mon 23/28:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 26/1C$ 256
Thu 12/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Thu 19/34:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 26/1C$ 257
Wed 18/210:00 a.m.
YYZ
-
ORD
1 stop5h 55m
Air Canada
Sat 21/27:15 a.m.
ORD
-
YYZ
1 stop5h 25m
Air Canada
Deal found 26/1C$ 259
Thu 19/23:30 p.m.
YYZ
-
ORD
Nonstop2h 09m
United Airlines
Mon 23/26:28 p.m.
ORD
-
YYZ
Nonstop1h 53m
United Airlines
Deal found 26/1C$ 260
Fri 24/49:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Sun 26/45:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 24/1C$ 263
Fri 12/68:15 a.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 14/68:45 a.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 25/1C$ 263
Wed 11/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Wed 18/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Deal found 25/1C$ 264
Wed 29/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Wed 6/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 23/1C$ 267

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 26 January 2026.

Round-trip from

C$ 247

One-way from

C$ 136

Popular in

January

Cheapest in

July

Average price

C$ 401

Good round-trip deal

C$ 263 or less

Good one-way deal

C$ 188 or less
WestJet
  • WestJet
  • 27/4-1/5
  • Nonstop
  • 7h 35m total
  • Canada to Chicago
Search Deals
WestJet
  • WestJet
  • 26/4
  • Nonstop
  • 3h 40m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Canada to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Canada to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Canada 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 26 January 2026.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Canada

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 17/2

9:00 p.m.-10:04 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Sat 28/3

6:25 p.m.-9:18 p.m.

Nonstop1h 53m

C$ 260

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 18/2

3:30 p.m.-4:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Sun 29/3

7:04 a.m.-9:54 a.m.

Nonstop1h 50m

C$ 260

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/3

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

Nonstop1h 50m

Chicago Midway

Thu 19/3

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

Nonstop1h 42m

C$ 268

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 17/3

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

Nonstop1h 50m

Chicago Midway

Sun 22/3

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

Nonstop1h 42m

C$ 270

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/6

10:35 a.m.-4:50 p.m.

1 stop7h 15m

Chicago Midway

Mon 8/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 2/6

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Thu 4/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 29/5

10:35 a.m.-4:50 p.m.

1 stop7h 15m

Chicago Midway

Mon 1/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 1/6

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Mon 8/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 4/6

12:25 p.m.-4:50 p.m.

1 stop5h 25m

Chicago Midway

Fri 5/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 28/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Mon 1/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 281

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/1

Showing 1-10 of 60 results
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Best time to book a flight from Canada to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada 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 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$ 112). 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 26 January 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 24 January 2026.

Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Monday 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.

Weekly flight availability from Canada to Chicago

Explore weekly flight availability from Canada 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 26 January 2026.

The most flights from CA0 to CHI are scheduled on a Monday (63 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (47 on average).

How often are flights from Canada to Chicago delayed?

About 12% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 138 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 7% of flights being delayed.

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 26 January 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
7.9
Good
412 reviews
Check prices

Boarding

8.2

Food

7.5

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Food

7.5

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,199 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Food

7.5

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,189 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Food

7.5

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,249 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Food

7.5

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,656 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Food

7.5

Entertainment

6.9

Comfort

7.9

Overall

7.9

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 3h 40m. WestJet provides one of the quickest options available for as low as C$ 247. Canada and Chicago are separated by a distance of 2223 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 Air Canada start at C$ 154 one-way.

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

    When deciding which route to take from Canada to Chicago consider Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl, Toronto Pearson 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: Japan Airlines (79%), Copa Airlines (76%), Republic Airways( 72%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 211. While the most popular route (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl) can be booked for C$ 278 on average, our data indicates C$ 1,673 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$ 112). 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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Pierre Elliott Trudeau Intl to O'Hare Intl flights
Pearson Intl to Midway flights
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Pearson Intl to Moline flights
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Saskatoon to Midway flights
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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 26 January 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 376FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
DeltaCheapestC$ 145AverageC$ 363FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 148AverageC$ 479FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 169AverageC$ 381FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 174AverageC$ 349FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 177AverageC$ 483FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Alaska AirlinesCheapestC$ 383AverageC$ 495FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines 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 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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