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Cheap flights from Canada to Chicago from C$ 128

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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
11 Jan — 18 Jan1
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 12 December 2025.

Wed 31/129:00 a.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Thu 1/18:51 a.m.ORD - YYZ
1 stop13h 55mUnited Airlines
Deal found 10/12C$ 319
Thu 25/127:40 p.m.YYZ - ORD
1 stop13h 07mUnited Airlines
Thu 1/18:51 a.m.ORD - YYZ
1 stop13h 55mUnited Airlines
Deal found 10/12C$ 325
Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 23/211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 11/12C$ 328
Thu 11/125:35 a.m.YYC - ORD
1 stop8h 35mAir Canada
Mon 15/127:05 a.m.ORD - YYC
1 stop17h 23mAir Canada
Deal found 11/12C$ 357
Thu 25/128:00 a.m.YUL - ORD
1 stop6h 01mAir Canada
Tue 30/128:30 p.m.ORD - YUL
1 stop12h 16mAir Canada
Deal found 11/12C$ 367
Wed 31/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/12C$ 374
Fri 26/126:50 a.m.YYZ - ORD
Nonstop2h 13mUnited Airlines
Wed 31/126:21 p.m.ORD - YYZ
1 stop4h 25mUnited Airlines
Deal found 10/12C$ 376
Thu 25/129:10 a.m.YUL - ORD
1 stop4h 51mAir Canada
Sun 28/128:30 p.m.ORD - YUL
1 stop4h 23mAir Canada
Deal found 11/12C$ 376
Wed 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 18/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/12C$ 379
Sat 27/126:00 a.m.YUL - ORD
1 stop5h 05mAir Canada
Mon 23/210:35 a.m.ORD - YUL
Nonstop2h 25mAir Canada
Deal found 11/12C$ 389
Fri 26/127:40 p.m.YYZ - ORD
1 stop5h 04mUnited Airlines
Tue 6/11:00 p.m.ORD - YYZ
1 stop6h 42mUnited Airlines
Deal found 10/12C$ 400
Thu 25/1210:10 a.m.YUL - ORD
1 stop6h 00mAir Canada
Sat 3/18:40 p.m.ORD - YUL
1 stop4h 13mAir Canada
Deal found 9/12C$ 401

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 12 December 2025.

Round-trip from

C$ 208

One-way from

C$ 128

Popular in

December

Cheapest in

July

Average price

C$ 441

Good round-trip deal

C$ 244 or less

Good one-way deal

C$ 152 or less
WestJet
  • WestJet
  • 20/2-23/2
  • Nonstop
  • 7h 30m total
  • Canada to Chicago
Search Deals
WestJet
  • WestJet
  • 12/1
  • Nonstop
  • 3h 35m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 13 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 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 12 December 2025.
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

Thu 15/1

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Wed 21/1

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 218

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 15/1

8:45 p.m.-9:13 a.m.

2 stops11h 28m

Chicago O'Hare Intl

Wed 21/1

7:00 a.m.-2:21 p.m.

1 stop8h 21m

C$ 226

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 247

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 26/5

8:30 a.m.-12:50 p.m.

Nonstop3h 20m

Chicago O'Hare Intl

Sat 30/5

7:15 a.m.-9:38 p.m.

1 stop15h 23m

C$ 250

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 15/2

6:15 a.m.-6:55 p.m.

1 stop11h 40m

Chicago O'Hare Intl

Tue 17/2

7:10 a.m.-9:53 p.m.

1 stop15h 43m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 25/1

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

Nonstop1h 50m

Chicago Midway

Sun 1/2

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

Nonstop1h 42m

C$ 258

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 18/2

9:25 a.m.-11:06 a.m.

Nonstop2h 41m

Chicago O'Hare Intl

Sun 22/2

12:50 p.m.-4:01 p.m.

Nonstop2h 11m

C$ 259

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 14/2

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Tue 17/2

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 259

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 5/2

3:50 p.m.-5:50 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Sun 8/2

11:50 a.m.-3:08 p.m.

Nonstop2h 18m

C$ 268

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 26/1

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

Nonstop1h 50m

Chicago Midway

Thu 29/1

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

Nonstop1h 42m

C$ 269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

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$ 113). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 196). 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 12 December 2025.

It’s typically best to fly out from Canada to Chicago in the afternoon. Doing so could potentially save you 20% 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 16 December 2024.

Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Tuesday evenings 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 12 December 2025.

The most flights from CA0 to CHI are scheduled on a Monday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 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 12 December 2025.
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
397 reviews
Check prices

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
397 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
9,095 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
11,049 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
3,194 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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
10,514 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

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. Air Canada provides one of the quickest options available for as low as C$ 247. 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$ 123 while deals on Air Canada start at C$ 155 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: Qatar Airways (86%), EVA Air (85%), SkyWest Airlines( 84%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 146. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 214 on average, our data indicates C$ 1,972 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$ 113). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 196). 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 6 airlines flying from Canada to Chicago

Discover the top 6 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 12 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 149AverageC$ 488FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 176AverageC$ 360FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 184AverageC$ 368FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 185AverageC$ 409FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 195AverageC$ 368FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 200AverageC$ 513FlexibilityNo cancel feeOn-time69%
Search United 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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