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Cheap flights from Canada to Chicago from C$ 140

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 24/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
29 Nov — 6 Dec1
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 30 October 2025.

Round-trip from

C$ 243

One-way from

C$ 140

Popular in

October

Cheapest in

July

Average price

C$ 413

Good round-trip deal

C$ 347 or less

Good one-way deal

C$ 197 or less
WestJet
  • WestJet
  • 30/1-2/3
  • Nonstop
  • 7h 30m total
  • Canada to Chicago
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WestJet
  • WestJet
  • 24/4
  • Nonstop
  • 3h 35m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 29 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 October 2025
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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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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 30 October 2025.

Fri 14/117:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Mon 17/118:15 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 29/10C$ 253
Wed 3/127:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Thu 12/22:00 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 29/10C$ 256
Wed 3/1210:58 a.m.YYZ - ORD
1 stop9h 23mAmerican Airlines
Thu 12/27:19 a.m.ORD - YYZ
1 stop4h 43mAmerican Airlines
Deal found 29/10C$ 257
Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 261
Thu 11/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 14/128:10 a.m.ORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 29/10C$ 264
Tue 18/116:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Thu 20/117:35 a.m.ORD - YYZ
1 stop4h 27mAmerican Airlines
Deal found 29/10C$ 265
Fri 14/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 17/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 265
Sat 1/111:29 p.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Mon 3/118:45 p.m.ORD - YYC
1 stop15h 59mAmerican Airlines
Deal found 28/10C$ 268
Sat 6/124:44 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Tue 9/126:22 a.m.ORD - YYZ
1 stop5h 38mAmerican Airlines
Deal found 28/10C$ 270
Thu 11/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 270
Fri 5/126:00 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 7/125:00 a.m.ORD - YYZ
1 stop5h 02mAmerican Airlines
Deal found 29/10C$ 271
Thu 13/117:00 a.m.YYZ - ORD
1 stop5h 18mAir Canada
Sun 16/118:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 30/10C$ 274

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 30 October 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

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 27/2

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

Nonstop2h 09m

Chicago O'Hare Intl

Sun 1/3

4:47 p.m.-7:45 p.m.

Nonstop1h 58m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 24/2

8:55 a.m.-10:02 a.m.

Nonstop2h 07m

Chicago O'Hare Intl

Sat 28/2

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 9/1

11:00 a.m.-12:08 p.m.

Nonstop2h 08m

Chicago O'Hare Intl

Sat 7/2

9:15 p.m.-11:54 p.m.

Nonstop1h 39m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 26/2

6:30 p.m.-7:30 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 1/3

2:00 p.m.-4:39 p.m.

Nonstop1h 39m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

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

Nonstop1h 50m

Chicago Midway

Mon 17/11

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

Nonstop1h 42m

C$ 265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Tue 18/11

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

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Mon 1/12

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

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 13/1

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

Nonstop1h 50m

Chicago Midway

Tue 20/1

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

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Fri 5/12

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

Nonstop1h 42m

C$ 281

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/12

6:24 p.m.-7:24 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Fri 5/12

9:39 a.m.-12:30 p.m.

Nonstop1h 51m

C$ 282

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/10

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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 116). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 198). 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 30 October 2025.

It’s typically best to fly out from Canada to Chicago in the evening. Doing so could potentially save you 24% 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. Sunday at noon 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 30 October 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
384 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,996 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,034 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,152 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,383 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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. United Airlines provides one of the quickest options available for as low as C$ 265. Canada and Chicago are separated by a distance of 711 km. Most flights are nonstop.

  • 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$ 152. United Airlines flights start at C$ 158 while deals on American Airlines start at C$ 159 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 Toronto Island - Chicago Midway 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: EVA Air (94%), Egyptair (90%), Copa Airlines( 90%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 221. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 214 on average, our data indicates C$ 2,048 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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 116). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 198). 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 151AverageC$ 486FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 178AverageC$ 429FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 179AverageC$ 444FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapestC$ 186AverageC$ 372FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Porter AirlinesCheapestC$ 198AverageC$ 402FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 208AverageC$ 524FlexibilityNo 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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