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Cheap flights from Canada to Chicago from C$ 135

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
15 Mar — 22 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 13 February 2026.

Fri 22/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 25/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 13/2C$ 227
Thu 16/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Sun 19/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 13/2C$ 233
Fri 1/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Thu 7/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 11/2C$ 236
Mon 27/41:20 p.m.
YUL
-
ORD
Nonstop2h 35m
Air Canada
Fri 1/53:40 p.m.
ORD
-
YUL
Nonstop2h 24m
Air Canada
Deal found 10/2C$ 238
Thu 26/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Sun 29/34:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Deal found 11/2C$ 238
Sat 14/39:25 a.m.
YUL
-
ORD
Nonstop2h 53m
Air Canada
Tue 17/37:15 a.m.
ORD
-
YUL
Nonstop2h 05m
Air Canada
Deal found 11/2C$ 240
Sat 28/36:00 a.m.
YUL
-
ORD
Nonstop3h 00m
United Airlines
Sat 4/46:01 p.m.
ORD
-
YUL
Nonstop2h 25m
United Airlines
Deal found 11/2C$ 241
Wed 25/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 30/311:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 11/2C$ 241
Thu 12/36:25 p.m.
YUL
-
ORD
Nonstop2h 45m
Air Canada
Mon 16/37:15 a.m.
ORD
-
YUL
Nonstop2h 05m
Air Canada
Deal found 12/2C$ 242
Mon 23/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Wed 25/311:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 13/2C$ 244
Thu 26/31:10 p.m.
YUL
-
ORD
Nonstop2h 45m
Air Canada
Sun 29/312:50 p.m.
ORD
-
YUL
Nonstop2h 11m
Air Canada
Deal found 13/2C$ 245
Wed 11/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Wed 18/311:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 10/2C$ 245

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 13 February 2026.

Round-trip from

C$ 227

One-way from

C$ 135

Popular in

February

Cheapest in

July

Average price

C$ 380

Good round-trip deal

C$ 259 or less

Good one-way deal

C$ 178 or less
Porter Airlines
  • Porter Airlines
  • 22/5-25/5
  • 2 total stops
  • 10h 00m total
  • Canada to Chicago
Search Deals
WestJet
  • WestJet
  • 10/5
  • Nonstop
  • 3h 40m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 13 February 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

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sun 24/5

6:30 p.m.-8:08 p.m.

Nonstop2h 38m

Chicago O'Hare Intl

Fri 29/5

8:45 a.m.-12:00 p.m.

Nonstop2h 15m

C$ 238

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 17/4

6:30 p.m.-8:05 p.m.

Nonstop2h 35m

Chicago O'Hare Intl

Sun 19/4

12:50 p.m.-4:05 p.m.

Nonstop2h 15m

C$ 252

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 4/5

6:35 p.m.-11:44 p.m.

1 stop6h 09m

Chicago O'Hare Intl

Sat 9/5

6:03 p.m.-9:26 p.m.

Nonstop2h 23m

C$ 260

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 17/3

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

Nonstop1h 50m

Chicago Midway

Mon 23/3

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

Nonstop1h 42m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 17/3

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$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/3

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

Nonstop1h 50m

Chicago Midway

Wed 25/3

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

Nonstop1h 42m

C$ 263

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 3/4

11:00 a.m.-12:03 p.m.

Nonstop2h 03m

Chicago O'Hare Intl

Mon 6/4

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

Nonstop1h 47m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 21/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

Chicago Midway

Sun 24/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 274

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/3

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

Nonstop1h 50m

Chicago Midway

Sun 8/3

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

Nonstop1h 42m

C$ 275

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/4

11:23 a.m.-4:04 p.m.

1 stop5h 41m

Chicago O'Hare Intl

Mon 13/4

4:20 p.m.-12:13 a.m.

1 stop6h 53m

C$ 275

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

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$ 109). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 185). 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 13 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 7 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.

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 13 February 2026.

The most flights from CA0 to CHI are scheduled on a Thursday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 13 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
7.9
Good
415 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.5

Comfort

7.9

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.
Porter Airlines
7.9
Good
415 reviews
Porter Airlines
7.9
Good
415 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.5

Comfort

7.9

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.
United Airlines
7.4
Good
9,289 reviews
Porter Airlines
7.9
Good
415 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.5

Comfort

7.9

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.
American Airlines
7.2
Good
11,288 reviews
Porter Airlines
7.9
Good
415 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.5

Comfort

7.9

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.
WestJet
7.2
Good
3,260 reviews
Porter Airlines
7.9
Good
415 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.5

Comfort

7.9

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.
Air Canada
7.1
Good
10,717 reviews
Porter Airlines
7.9
Good
415 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.5

Comfort

7.9

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

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. Air Canada provides one of the quickest options available for as low as C$ 261. 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$ 115. Porter Airlines flights start at C$ 122 while deals on Air Canada start at C$ 153 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: Copa Airlines (79%), Egyptair (72%), Japan Airlines( 70%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 222. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 285 on average, our data indicates C$ 1,844 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$ 109). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 185). 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

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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 13 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 383FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 120AverageC$ 470FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 144AverageC$ 363FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 166AverageC$ 468FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 168AverageC$ 376FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 173AverageC$ 347FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Alaska AirlinesCheapestC$ 381AverageC$ 492FlexibilityNo 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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