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Cheap flights from Chicago to Canada from C$ 100

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 7/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
28 May — 4 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Canada

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Canada
Explore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 April 2026.

Thu 16/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 19/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/4C$ 290
Fri 15/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Multiple Airlines
Mon 18/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 27/4C$ 292
Fri 15/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Multiple Airlines
Tue 19/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 25/4C$ 293
Wed 27/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Fri 29/51:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/4C$ 294
Fri 31/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Fri 7/81:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 26/4C$ 296
Thu 30/73:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 1/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/4C$ 297
Mon 11/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 17/58:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 25/4C$ 299
Tue 21/710:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 25/78:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 26/4C$ 300
Wed 27/56:30 a.m.
ORD
-
YYZ
1 stop6h 49m
United Airlines
Wed 27/55:15 p.m.
YYZ
-
ORD
Nonstop2h 04m
United Airlines
Deal found 23/4C$ 300
Fri 8/510:30 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 16/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 23/4C$ 301
Tue 4/89:50 a.m.
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Sun 9/88:05 a.m.
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 26/4C$ 301
Tue 11/83:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 13/88:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 23/4C$ 303

Find flight deals from Chicago to Canada

Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated 28 April 2026.

Round-trip from

C$ 290

One-way from

C$ 100

Popular in

April

Cheapest in

September

Average price

C$ 423

Good round-trip deal

C$ 138 or less

Good one-way deal

C$ 132 or less
Porter Airlines
  • Porter Airlines
  • 16/7-19/7
  • Nonstop
  • 3h 30m total
  • Chicago to Canada
Search Deals
Porter Airlines
  • Porter Airlines
  • 7/6
  • 1 total stop
  • 6h 00m total
  • Chicago to Canada
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 9 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 Chicago (CHI) to Canada.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Canada.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Canada 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 28 April 2026.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 20/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Fri 22/5

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

Nonstop1h 50m

C$ 292

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 21/7

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

Nonstop1h 40m

Toronto Island

Sat 25/7

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

Nonstop1h 50m

C$ 300

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 26/5

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

Nonstop1h 40m

Toronto Island

Sat 30/5

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

Nonstop1h 50m

C$ 308

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 13/8

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

Nonstop1h 40m

Toronto Island

Sun 16/8

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

Nonstop1h 50m

C$ 308

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/7

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

Nonstop1h 40m

Toronto Island

Mon 20/7

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

Nonstop1h 50m

C$ 308

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 4/6

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

Nonstop1h 44m

Toronto Pearson Intl

Sun 7/6

2:45 p.m.-3:50 p.m.

Nonstop2h 05m

C$ 320

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 27/5

12:55 p.m.-3:46 p.m.

Nonstop1h 51m

Toronto Pearson Intl

Sun 31/5

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

Nonstop2h 06m

C$ 320

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 11/6

8:50 a.m.-11:49 a.m.

Nonstop1h 59m

Toronto Pearson Intl

Mon 15/6

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

Nonstop2h 00m

C$ 320

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 9/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Sun 17/5

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

Nonstop1h 50m

C$ 323

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 25/7

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

Nonstop1h 40m

Toronto Island

Sat 1/8

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

Nonstop1h 50m

C$ 326

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Canada

Have a flexible travel schedule? Discover the best time to fly to Canada from Chicago 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 Chicago to Canada

How far ahead should I book a flight from Chicago to Canada?

Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Canada. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Canada?

Currently, October is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 322). Flying from Chicago to Canada in December is currently the most expensive (average of C$ 571). 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 CHI to CA?

Find hourly flight availability from Chicago to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 28 April 2026.

It’s typically best to fly out from Chicago to Canada in the afternoon. Doing so could potentially save you 30% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to Canada?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Canada. Price data was last updated on 25 April 2026.

Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Friday mornings when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Canada

Explore weekly flight availability from Chicago to Canada. 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 28 April 2026.

The most flights from CHI to CA0 are scheduled on a Monday (69 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (35 on average).

How often are flights from Chicago to Canada delayed?

About 21% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 136 minutes.

What is the most punctual flight time for Chicago to Canada flights?

Historically, flights departing in the morning 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 Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Canada flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 18% of flights being delayed.

Reviews of airlines servicing Canada

Get insights into the airlines that provide service to Canada. 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 Canada. Reviews last updated 28 April 2026.
Get a feel of what it's like to fly with Porter Airlines,United Airlines, andWestJet from Chicago to Canada by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
435 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

7.0

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

Comfort

8.0

Boarding

8.2

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

7.0

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
9,672 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

7.0

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
3,327 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

7.0

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
10,974 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

7.0

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 Chicago to Canada. 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 Chicago to Canada?

    Porter Airlines, United Airlines, and Delta can get you from Chicago to Canada in just under 1h 40m. Your travel time can differ by up to 7h 01m. Airlines will cover a distance of 711 km. Both multi-stop and direct flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Canada one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 40. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Chicago to Canada for a low price.

  • What are the most popular routes from Chicago to Canada?

    Most travellers choose Chicago O'Hare Intl - Vancouver Intl, Chicago O'Hare Intl - Calgary or Chicago O'Hare Intl - Toronto Pearson Intl when deciding on the best route from Chicago to Canada.

  • What are the most reliable airlines from Chicago to Canada?

    Before booking your flight to Canada from Chicago, check out the most reliable airlines to get you to your destination on time: Finnair (100%), Korean Air (91%), Republic Airways( 75%).

  • What are the cheapest flights from Chicago to Canada?

    Looking for the cheapest flight from Chicago to Canada? While on average our users pay C$ 379, our data indicates the cheapest price to be C$ 117. The most popular route (Chicago O'Hare Intl - Vancouver Intl), is priced around C$ 466.

  • Can I find deals for flights from Chicago to Canada that include hotel bookings?

    Yes. In addition to deals on Chicago to Canada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Canada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Canada.

  • Can I find deals for business class flights from Chicago to Canada?

    Yes. Cheapflights offers flight deals from Chicago to Canada 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 Chicago to Canada?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 322). Flying from Chicago to Canada in December is currently the most expensive (average of C$ 571). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Chicago to Canada

Discover the top 4 airlines that operate flights from Chicago to Canada. 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 28 April 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 133AverageC$ 675FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 168AverageC$ 440FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 251AverageC$ 397FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 261AverageC$ 366FlexibilityNo cancel feeOn-time67%
Search Air Canada 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 Chicago to Canada?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Chicago to Canada. 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 Chicago to Canada?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Canada.

Can Cheapflights find flights from Chicago to Canada with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Canada, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago to Canada become cheaper?

Not ready to book yet? You can track prices for flights from Chicago to Canada on Cheapflights with our Price Alert feature and get notified when better prices are available.

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