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Cheap flights from Canada to Chicago from C$ 143

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
14 Feb — 21 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated 15 January 2026.

Round-trip from

C$ 229

One-way from

C$ 143

Popular in

January

Cheapest in

July

Average price

C$ 402

Good round-trip deal

C$ 320 or less

Good one-way deal

C$ 199 or less
Air Canada
  • Air Canada
  • 28/2-7/3
  • 2 total stops
  • 17h 44m total
  • Canada to Chicago
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WestJet
  • WestJet
  • 10/4
  • Nonstop
  • 3h 35m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 60 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 January 2026
Search Deals
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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Find 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 15 January 2026.

Fri 27/29:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 6/32:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 12/1C$ 206
Sat 28/25:30 a.m.
YYC
-
ORD
1 stop8h 40m
Air Canada
Sat 7/33:55 p.m.
ORD
-
YYC
1 stop9h 04m
Air Canada
Deal found 14/1C$ 229
Fri 6/29:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 13/22:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 13/1C$ 233
Thu 30/412:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Sun 3/55:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 13/1C$ 240
Sat 30/512:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Sun 31/55:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 14/1C$ 243
Wed 26/811:55 p.m.
YYC
-
ORD
1 stop8h 05m
Air Canada
Sat 29/82:15 p.m.
ORD
-
YYC
1 stop7h 45m
Air Canada
Deal found 13/1C$ 252
Wed 11/27:00 a.m.
YUL
-
ORD
1 stop7h 15m
United Airlines
Thu 19/27:10 a.m.
ORD
-
YUL
1 stop5h 18m
United Airlines
Deal found 13/1C$ 254
Thu 5/29:25 a.m.
YUL
-
ORD
Nonstop2h 41m
Air Canada
Sun 8/23:35 p.m.
ORD
-
YUL
Nonstop2h 05m
Air Canada
Deal found 13/1C$ 256
Thu 5/26:45 p.m.
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Sun 8/210:00 a.m.
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 14/1C$ 257
Tue 31/36:00 a.m.
YYC
-
ORD
1 stop14h 17m
United Airlines
Wed 8/412:55 p.m.
ORD
-
YYC
1 stop9h 53m
United Airlines
Deal found 13/1C$ 257
Sat 14/26:25 p.m.
YUL
-
ORD
Nonstop2h 45m
Air Canada
Sat 21/27:15 a.m.
ORD
-
YUL
Nonstop2h 05m
Air Canada
Deal found 14/1C$ 257
Fri 6/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Air Transat
Sun 8/24:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Air Transat
Deal found 14/1C$ 258

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 15 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

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 27/2

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 206

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 11/2

7:00 a.m.-12:05 p.m.

1 stop6h 05m

Chicago O'Hare Intl

Wed 18/2

6:00 a.m.-1:28 p.m.

1 stop6h 28m

C$ 254

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 31/3

6:00 a.m.-9:17 p.m.

1 stop14h 17m

Chicago O'Hare Intl

Wed 8/4

12:55 p.m.-9:48 p.m.

1 stop9h 53m

C$ 257

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 27/3

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

Nonstop1h 50m

Chicago Midway

Tue 31/3

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

Nonstop1h 42m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 30/1

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

Nonstop1h 50m

Chicago Midway

Sun 1/2

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

Nonstop1h 42m

C$ 260

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 30/1

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

Nonstop1h 50m

Chicago Midway

Mon 2/2

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

Nonstop1h 42m

C$ 261

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 6/2

4:45 p.m.-6:51 p.m.

Nonstop3h 06m

Chicago O'Hare Intl

Mon 9/2

3:35 p.m.-9:42 p.m.

1 stop5h 07m

C$ 263

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 18/3

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$ 263

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 10/2

4:45 p.m.-6:51 p.m.

Nonstop3h 06m

Chicago O'Hare Intl

Tue 17/2

7:10 a.m.-1:28 p.m.

1 stop5h 18m

C$ 263

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 4/2

4:45 p.m.-6:51 p.m.

Nonstop3h 06m

Chicago O'Hare Intl

Sat 7/2

8:52 a.m.-7:48 p.m.

1 stop9h 56m

C$ 263

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/1

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$ 114). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 189). 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 15 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 10 January 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 15 January 2026.

The most flights from CA0 to CHI are scheduled on a Thursday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).

How often are flights from Canada to Chicago delayed?

About 11% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 139 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 Saturday 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 6% 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 15 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
8.0
Very good
408 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

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
8.0
Very good
408 reviews
Porter Airlines
8.0
Very good
408 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

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
9,164 reviews
Porter Airlines
8.0
Very good
408 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

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
11,136 reviews
Porter Airlines
8.0
Very good
408 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

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
3,243 reviews
Porter Airlines
8.0
Very good
408 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

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
10,624 reviews
Porter Airlines
8.0
Very good
408 reviews
Check prices

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

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 1h 50m. WestJet provides one of the quickest options available for as low as C$ 258. 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$ 117. Porter Airlines flights start at C$ 124 while deals on Air Canada start at C$ 156 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: Japan Airlines (82%), Copa Airlines (75%), Egyptair( 73%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 230. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 264 on average, our data indicates C$ 1,846 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$ 114). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 189). 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.
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
Calgary 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
Ottawa to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Calgary to Midway flights
Vancouver Intl to St. Louis flights
Pierre Elliott Trudeau Intl to St. Louis flights
Seattle to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Ottawa to Midway flights
Halifax to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Québec City to O'Hare Intl flights
Calgary to St. Louis flights
Halifax to Midway flights
Edmonton to Midway flights
Québec City to Midway flights
Halifax to St. Louis flights
Saskatoon to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Victoria to O'Hare Intl flights
Ottawa to St. Louis flights
Kelowna to O'Hare Intl flights
Saskatoon to Midway flights
Edmonton to St. Louis flights
Vancouver Intl to Peoria flights
St John to O'Hare Intl flights
Detroit to O'Hare Intl flights
Pearson Intl to Bloomington flights
London to O'Hare Intl flights
Regina to O'Hare Intl flights
Region of Waterloo Intl to O'Hare Intl flights
Kelowna to Midway flights
Sudbury to O'Hare Intl flights
Pearson Intl to Peoria flights

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 15 January 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapestC$ 147AverageC$ 368FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 150AverageC$ 487FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 172AverageC$ 384FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 177AverageC$ 359FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 180AverageC$ 512FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 190AverageC$ 380FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Alaska AirlinesCheapestC$ 389AverageC$ 502FlexibilityNo 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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