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Cheap flights from Chicago to Canada from C$ 98

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
28 Nov — 5 Dec1
1 adult
1 adult, Economy, 0 bags

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 29 October 2025.

Round-trip from

C$ 234

One-way from

C$ 98

Popular in

January

Cheapest in

September

Average price

C$ 417

Good round-trip deal

C$ 124 or less

Good one-way deal

C$ 137 or less
WestJet
  • WestJet
  • 20/2-23/2
  • Nonstop
  • 7h 30m total
  • Chicago to Canada
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WestJet
  • WestJet
  • 26/4
  • Nonstop
  • 3h 49m total
  • Chicago to Canada
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 67 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 October 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

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 29 October 2025.

Wed 19/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 22/1111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 29/10C$ 262
Wed 12/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 28/10C$ 265
Fri 5/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 7/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 28/10C$ 266
Thu 13/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 27/10C$ 267
Fri 5/122:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Mon 8/129:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 27/10C$ 269
Wed 12/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 13/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 29/10C$ 269
Fri 14/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 27/10C$ 270
Sat 6/126:04 a.m.ORD - YYZ
1 stop4h 52mAmerican Airlines
Sun 7/126:24 p.m.YYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 27/10C$ 270
Wed 3/122:49 p.m.MDW - YVR
1 stop22h 23mMultiple Airlines
Sun 7/1211:00 p.m.YVR - MDW
1 stop8h 52mMultiple Airlines
Deal found 29/10C$ 272
Wed 3/124:01 p.m.ORD - YVR
1 stop21h 11mMultiple Airlines
Sun 7/1211:00 p.m.YVR - ORD
1 stop16h 27mMultiple Airlines
Deal found 27/10C$ 272
Thu 13/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 14/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 28/10C$ 273
Tue 11/1110:46 a.m.ORD - YQB
Nonstop2h 27mUnited Airlines
Sat 15/112:55 p.m.YQB - ORD
Nonstop3h 02mUnited Airlines
Deal found 27/10C$ 276

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 29 October 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

Fri 5/12

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

Nonstop1h 42m

Toronto Island

Sun 7/12

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

Nonstop1h 50m

C$ 265

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 4/3

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

Nonstop1h 42m

Toronto Island

Sat 7/3

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/3

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

Nonstop1h 42m

Toronto Island

Sat 7/3

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 13/11

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

Nonstop1h 42m

Toronto Island

Sun 16/11

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

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 3/3

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

Nonstop1h 42m

Toronto Island

Sat 7/3

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/11

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

Nonstop1h 42m

Toronto Island

Thu 13/11

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

Nonstop1h 50m

C$ 269

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 14/11

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

Nonstop1h 42m

Toronto Island

Sun 16/11

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

Nonstop1h 50m

C$ 270

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/11

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

Nonstop1h 42m

Toronto Island

Sat 22/11

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

C$ 274

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Tue 11/11

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

Nonstop2h 27m

Québec City

Sat 15/11

2:55 p.m.-4:57 p.m.

Nonstop3h 02m

C$ 276

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Tue 14/4

12:50 p.m.-6:11 p.m.

1 stop4h 21m

Québec City

Wed 15/4

10:55 a.m.-2:55 p.m.

1 stop5h 00m

C$ 291

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/10

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, April is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 111). Flying from Chicago to Canada in August is currently the most expensive (average of C$ 184). 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 29 October 2025.

It’s typically best to fly out from Chicago to Canada in the evening. Doing so could potentially save you 21% on the flight price compared to flying at noon, 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 16 December 2024.

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

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 29 October 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
8.0
Very good
384 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

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

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

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
8,998 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

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
3,149 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

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
10,377 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

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 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 Air Canada can get you from Chicago to Canada in just under 1h 42m. Your travel time can differ by up to 2h 39m. 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 United Airlines, with whom users have recently found tickets for as low as C$ 102. However, be on the lookout for offers from Air Canada and Porter 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 - Toronto Pearson Intl, Chicago O'Hare Intl - Vancouver Intl or Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau 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 (92%), Qatar Airways (91%), British Airways( 89%).

  • 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$ 405, our data indicates the cheapest price to be C$ 113. The most popular route (Chicago O'Hare Intl - Toronto Pearson Intl), is priced around C$ 231.

  • 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, April is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 111). Flying from Chicago to Canada in August is currently the most expensive (average of C$ 184). 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 29 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 172AverageC$ 455FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 205AverageC$ 608FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 213AverageC$ 350FlexibilityNo 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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