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Cheap flights from Chicago to Canada from C$ 92

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 20/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
26 Jan — 2 Feb1
1 adult

Cheap flight deals from Chicago to Canada

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Canada (CA0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 21 January 2025.

Round-trip from

C$ 227

One-way from

C$ 92

Good round-trip deal

C$ 231 or less

Good one-way deal

C$ 213 or less
WestJet
  • WestJet
  • 10/3-24/3
  • Nonstop
  • 7h 17m total
  • Chicago to Canada
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WestJet
  • WestJet
  • 20/4
  • Nonstop
  • 3h 51m total
  • Chicago to Canada
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Canada.
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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 21 January 2025.

Mon 10/34:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Mon 24/311:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Deal found 20/1C$ 227
Thu 20/24:45 p.m.ORD - YYC
Nonstop3h 51mMultiple Airlines
Thu 27/26:15 a.m.YYC - ORD
1 stop7h 36mMultiple Airlines
Deal found 20/1C$ 258
Thu 20/24:45 p.m.ORD - YVR
1 stop7h 41mWestJet
Thu 27/26:30 a.m.YVR - ORD
1 stop7h 26mWestJet
Deal found 20/1C$ 275
Thu 13/21:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 16/211:20 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 20/1C$ 284
Sat 17/57:10 a.m.ORD - YYC
1 stop15h 38mUnited Airlines
Sat 24/58:30 a.m.YYC - ORD
Nonstop3h 19mUnited Airlines
Deal found 20/1C$ 294
Thu 13/21:05 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Sun 16/211:20 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 21/1C$ 314
Tue 4/31:32 p.m.ORD - YVR
1 stop10h 58mMultiple Airlines
Tue 11/33:55 p.m.YVR - ORD
1 stop12h 41mMultiple Airlines
Deal found 20/1C$ 325
Tue 9/97:45 p.m.ORD - YYC
Nonstop3h 44mAir Canada
Tue 9/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Deal found 20/1C$ 330
Sat 22/312:55 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Wed 26/39:30 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 20/1C$ 346
Fri 28/21:05 p.m.MDW - YUL
1 stop5h 20mPorter Airlines
Sun 2/36:50 a.m.YUL - MDW
1 stop4h 30mPorter Airlines
Deal found 20/1C$ 356
Mon 10/21:26 p.m.MDW - YYC
1 stop8h 27mDelta
Sun 16/26:35 a.m.YYC - MDW
1 stop10h 08mDelta
Deal found 20/1C$ 360
Wed 19/21:45 p.m.ORD - YYC
1 stop10h 30mDelta
Sun 23/26:35 a.m.YYC - ORD
1 stop9h 54mDelta
Deal found 19/1C$ 360

Find flights from Chicago to Canada within your budget

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 21 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 10/3

4:45 p.m.-7:36 p.m.

Nonstop3h 51m

Calgary

Mon 24/3

11:30 a.m.-3:56 p.m.

Nonstop3h 26m

C$ 227

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 20/2

4:45 p.m.-7:36 p.m.

Nonstop3h 51m

Calgary

Thu 27/2

6:15 a.m.-2:51 p.m.

1 stop7h 36m

C$ 258

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Thu 20/2

4:45 p.m.-10:26 p.m.

1 stop7h 41m

Vancouver Intl

Thu 27/2

6:30 a.m.-3:56 p.m.

1 stop7h 26m

C$ 275

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 13/2

1:05 p.m.-3:47 p.m.

Nonstop1h 42m

Toronto Island

Sun 16/2

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

C$ 284

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 17/5

7:10 a.m.-9:48 p.m.

1 stop15h 38m

Calgary

Sat 24/5

8:30 a.m.-12:49 p.m.

Nonstop3h 19m

C$ 294

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 6/3

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

Toronto Island

Thu 13/3

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

C$ 305

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Tue 4/3

1:32 p.m.-10:30 p.m.

1 stop10h 58m

Vancouver Intl

Tue 11/3

3:55 p.m.-6:36 a.m.

1 stop12h 41m

C$ 325

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 8/2

2:05 p.m.-9:18 p.m.

1 stop8h 13m

Calgary

Tue 11/2

8:30 a.m.-6:38 p.m.

1 stop9h 08m

C$ 338

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 22/3

12:55 p.m.-3:37 p.m.

Nonstop1h 42m

Toronto Island

Wed 26/3

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

C$ 346

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 28/2

1:05 p.m.-7:25 p.m.

1 stop5h 20m

Montreal Pierre Elliott Trudeau Intl

Sun 2/3

6:50 a.m.-10:20 a.m.

1 stop4h 30m

C$ 356

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/1

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.

Travel insights for flights from Chicago to Canada

Get recent, data-driven insights about flights from Chicago to Canada including ideal travel times, pricing trends, and more.

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 21 January 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 21 January 2025.

The most flights from CHI to CA0 are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

Rainfall in Canada by month

Plan your trip to Canada by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Canada ranges from 51.0 - 83.0 mm per month. June is typically the wettest month, when rainfall can reach 83.0 mm. February is typically the driest time to visit Canada when rainfall is around 51.0 mm.

Temperature in Canada by month

Plan your trip to Canada by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Canada, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 21.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -6.0 C).

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 21 January 2025.
Get a feel of what it's like to fly with WestJet, Delta and American Airlines from Chicago to Canada by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Japan Airlines
8.3
Very good
1,449 reviews
Check prices

Comfort

8.2

Food

7.7

Crew

8.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Japan Airlines
8.3
Very good
1,449 reviews
Japan Airlines
8.3
Very good
1,449 reviews
Check prices

Comfort

8.2

Food

7.7

Crew

8.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Delta
8.0
Very good
8,521 reviews
Japan Airlines
8.3
Very good
1,449 reviews
Check prices

Comfort

8.2

Food

7.7

Crew

8.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Alaska Airlines
8.0
Very good
9,706 reviews
Japan Airlines
8.3
Very good
1,449 reviews
Check prices

Comfort

8.2

Food

7.7

Crew

8.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Porter Airlines
7.9
Good
277 reviews
Japan Airlines
8.3
Very good
1,449 reviews
Check prices

Comfort

8.2

Food

7.7

Crew

8.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

KLM
7.8
Good
1,341 reviews
Japan Airlines
8.3
Very good
1,449 reviews
Check prices

Comfort

8.2

Food

7.7

Crew

8.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 10

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

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.

  • 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$ 92. However, be on the lookout for offers from United Airlines and Air Canada, 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: Royal Jordanian (94%), Egyptair (91%), Qatar Airways( 90%).

  • 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$ 564, our data indicates the cheapest price to be C$ 206. The most popular route (Chicago O'Hare Intl - Vancouver Intl), is priced around C$ 357.

  • 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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Midway to Québec City flights
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Midway to Ottawa flights
St. Louis to Calgary flights
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Midway to Kelowna flights
St. Louis to Edmonton flights
O'Hare Intl to Regina flights
O'Hare Intl to Hamilton flights
O'Hare Intl to Prince George flights

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 21 January 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 143AverageC$ 477FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 189AverageC$ 559FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 192AverageC$ 762FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 314AverageC$ 438FlexibilityNo cancel feeOn-time52%
Search Porter 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 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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