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Cheap flights from Chicago to Canada from C$ 83

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Chicago to Canada

Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated 11 September 2025.

Round-trip from

C$ 193

One-way from

C$ 83

Popular in

January

Cheapest in

July

Average price

C$ 382

Good round-trip deal

C$ 171 or less

Good one-way deal

C$ 80 or less
WestJet
  • WestJet
  • 10/10-17/10
  • Nonstop
  • 7h 17m total
  • Chicago to Canada
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Air Canada
  • Air Canada
  • 3/11
  • 1 total stop
  • 4h 24m total
  • Chicago to Canada
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 53 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 September 2025
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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.
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Find flight deals from Chicago to Canada

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 11 September 2025.

Fri 10/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Fri 17/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 10/9C$ 193
Sat 11/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 18/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 194
Fri 10/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Thu 16/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 197
Sun 12/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 18/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 198
Sat 18/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Fri 24/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Deal found 9/9C$ 200
Thu 16/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Sun 19/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Deal found 9/9C$ 201
Sat 11/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sun 12/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 202
Fri 31/102:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Mon 3/119:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 9/9C$ 204
Mon 6/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Thu 16/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 205
Sun 26/102:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Sun 2/119:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 11/9C$ 206
Sat 18/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Sat 25/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Deal found 9/9C$ 208
Thu 9/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Sat 18/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 9/9C$ 208

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 11 September 2025.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.

Fly from

Chicago

Fly to

Canada

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 8/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 237

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 22/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 5/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Tue 11/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 256

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 27/10

10:46 a.m.-2:13 p.m.

Nonstop2h 27m

Québec City

Thu 30/10

6:00 a.m.-11:18 a.m.

1 stop6h 18m

C$ 256

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 6/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Tue 11/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 256

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Sun 2/11

10:46 a.m.-2:13 p.m.

Nonstop2h 27m

Québec City

Mon 17/11

6:00 a.m.-11:18 a.m.

1 stop6h 18m

C$ 256

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 31/10

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Mon 3/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 256

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 27/10

9:56 a.m.-1:36 p.m.

Nonstop2h 40m

Québec City

Fri 31/10

4:14 p.m.-6:04 p.m.

Nonstop2h 50m

C$ 261

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 27/10

9:56 a.m.-1:36 p.m.

Nonstop2h 40m

Québec City

Thu 30/10

4:14 p.m.-6:04 p.m.

Nonstop2h 50m

C$ 261

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 60 results
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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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 168). Flying from Chicago to Canada in July is currently the most expensive (average of C$ 258). 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 11 September 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Canada as you normally would.

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 11 September 2025.

The most flights from CHI to CA0 are scheduled on a Thursday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

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 11 September 2025.
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
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

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
8,937 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

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
3,091 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Boarding

8.1

Entertainment

7.0

Comfort

7.9

Food

7.6

Crew

8.6

Overall

7.9

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 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 American Airlines can get you from Chicago to Canada in just under 1h 42m. Your travel time will be generally consistent. Airlines will cover a distance of 711 km. Generally, flights for this route are direct.

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

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as C$ 90. However, be on the lookout for offers from United Airlines and WestJet, 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 - Montreal Pierre Elliott Trudeau Intl, Chicago O'Hare Intl - Toronto Pearson Intl or Chicago O'Hare Intl - Vancouver 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: Qatar Airways (85%), Envoy Air (80%), SkyWest Airlines( 80%).

  • 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$ 472, our data indicates the cheapest price to be C$ 124. The most popular route (Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl), is priced around C$ 380.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 168). Flying from Chicago to Canada in July is currently the most expensive (average of C$ 258). 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 Chicago to Canada

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Canada

Discover the top 3 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 171AverageC$ 414FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 204AverageC$ 725FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 212AverageC$ 381FlexibilityNo cancel feeOn-time60%
Search WestJet 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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