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Cheap flights from Canada to Chicago from C$ 160

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
23 May — 30 May1
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 23 April 2026.

Wed 20/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Wed 27/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 22/4C$ 236
Mon 25/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 28/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 21/4C$ 238
Wed 27/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Thu 28/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 21/4C$ 243
Fri 22/512:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Fri 29/55:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 22/4C$ 251
Fri 29/56:15 a.m.
YYC
-
ORD
Nonstop3h 30m
American Airlines
Sun 7/68:50 p.m.
ORD
-
YYC
Nonstop3h 52m
American Airlines
Deal found 21/4C$ 277
Tue 5/51:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 8/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/4C$ 279
Thu 3/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 6/911:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/4C$ 279
Sun 17/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 20/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/4C$ 280
Thu 4/68:50 a.m.
YYZ
-
ORD
Nonstop2h 00m
Lufthansa
Sun 7/67:09 a.m.
ORD
-
YYZ
Nonstop1h 45m
Lufthansa
Deal found 21/4C$ 281
Fri 24/71:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 26/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/4C$ 281
Thu 25/612:15 p.m.
YTZ
-
ORD
Nonstop1h 55m
Air Canada
Sun 28/62:00 p.m.
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 19/4C$ 281
Thu 7/51:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 10/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/4C$ 283

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 23 April 2026.

Round-trip from

C$ 236

One-way from

C$ 160

Popular in

April

Cheapest in

July

Average price

C$ 436

Good round-trip deal

C$ 265 or less

Good one-way deal

C$ 158 or less
WestJet
  • WestJet
  • 20/5-27/5
  • Nonstop
  • 7h 35m total
  • Canada to Chicago
Search Deals
WestJet
  • WestJet
  • 11/5
  • 1 total stop
  • 8h 40m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 23 April 2026.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 5/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Fri 8/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 279

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Thu 11/6

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

Nonstop1h 40m

C$ 288

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 29/5

7:43 p.m.-11:26 p.m.

1 stop4h 43m

Chicago O'Hare Intl

Sun 31/5

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 295

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 12/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Wed 13/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 301

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 2/8

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Wed 5/8

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

Nonstop1h 40m

C$ 302

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 20/7

7:20 p.m.-8:16 p.m.

Nonstop1h 56m

Chicago O'Hare Intl

Thu 23/7

2:00 p.m.-4:41 p.m.

Nonstop1h 41m

C$ 303

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Mon 31/8

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 303

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 22/5

1:00 p.m.-2:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Mon 25/5

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 313

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 20/5

10:15 a.m.-11:18 a.m.

Nonstop2h 03m

Chicago O'Hare Intl

Wed 27/5

6:30 a.m.-2:19 p.m.

1 stop6h 49m

C$ 313

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 30/6

8:50 a.m.-9:50 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sat 4/7

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

C$ 316

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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, November is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 370). Flying from Canada to Chicago in April is currently the most expensive (average of C$ 509). 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 23 April 2026.

It’s typically best to fly out from Canada to Chicago in the afternoon. 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 18 April 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. Sunday 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 23 April 2026.

The most flights from CA0 to CHI are scheduled on a Monday (71 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 13% 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?

Thursday 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 8% 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 23 April 2026.
Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet 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
435 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,635 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,324 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,659 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,957 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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. Porter Airlines provides one of the quickest options available for as low as C$ 279. 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 Porter Airlines, which is currently one of the cheapest options available, starting at C$ 122. WestJet flights start at C$ 134 while deals on Air Canada start at C$ 141 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: Copa Airlines (91%), EVA Air (78%), Republic Airways( 73%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 226. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 272 on average, our data indicates C$ 1,294 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, November is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 370). Flying from Canada to Chicago in April is currently the most expensive (average of C$ 509). 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 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 23 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 112AverageC$ 419FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 119AverageC$ 500FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 147AverageC$ 384FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 166AverageC$ 457FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 175AverageC$ 375FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 175AverageC$ 399FlexibilityNo cancel feeOn-time71%
Search American 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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