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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 28/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
17 Jun — 24 Jun1
1 adult

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 12 June 2025.

Round-trip from

C$ 215

One-way from

C$ 100

Popular in

November

Cheapest in

July

Average price

C$ 383

Good round-trip deal

C$ 157 or less

Good one-way deal

C$ 111 or less
WestJet
  • WestJet
  • 17/7-22/7
  • Nonstop
  • 7h 18m total
  • Chicago to Canada
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American Airlines
  • American Airlines
  • 28/9
  • Nonstop
  • 3h 49m total
  • Chicago to Canada
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 38 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 June 2025
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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 12 June 2025.

Thu 17/75:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Tue 22/712:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Deal found 10/6C$ 215
Thu 18/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 20/97:30 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 12/6C$ 231
Mon 14/75:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Tue 22/71:10 a.m.YYC - ORD
1 stop6h 59mMultiple Airlines
Deal found 10/6C$ 235
Mon 29/92:00 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Wed 1/104:40 p.m.YYZ - ORD
Nonstop1h 53mAir Canada
Deal found 12/6C$ 237
Thu 18/99:31 p.m.ORD - YYZ
1 stop11h 33mUnited Airlines
Wed 24/95:15 p.m.YYZ - ORD
Nonstop1h 57mUnited Airlines
Deal found 10/6C$ 242
Mon 25/85:30 p.m.ORD - YEG
1 stop7h 57mWestJet
Wed 27/88:00 a.m.YEG - ORD
1 stop7h 44mWestJet
Deal found 10/6C$ 245
Tue 24/69:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Thu 26/67:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 12/6C$ 269
Mon 22/93:35 p.m.ORD - YYC
1 stop8h 41mAir Canada
Mon 29/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Deal found 11/6C$ 276
Sat 13/98:08 p.m.ORD - YYC
Nonstop3h 45mUnited Airlines
Wed 17/96:15 a.m.YYC - ORD
1 stop12h 42mUnited Airlines
Deal found 12/6C$ 279
Tue 15/76:00 a.m.ORD - YYZ
1 stop5h 05mAmerican Airlines
Tue 15/73:45 p.m.YYZ - ORD
1 stop6h 46mAmerican Airlines
Deal found 12/6C$ 282
Wed 13/89:40 a.m.MDW - YTZ
Nonstop1h 40mAir Transat
Sat 16/87:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Deal found 11/6C$ 295
Fri 13/68:30 p.m.ORD - YYC
Nonstop3h 59mAmerican Airlines
Mon 16/66:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 11/6C$ 299

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 12 June 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

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 17/7

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Tue 22/7

12:15 p.m.-4:44 p.m.

Nonstop3h 29m

C$ 215

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 18/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Sat 20/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

C$ 231

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 14/7

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Tue 22/7

1:10 a.m.-9:09 a.m.

1 stop6h 59m

C$ 235

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 29/9

2:00 p.m.-4:43 p.m.

Nonstop1h 43m

Toronto Pearson Intl

Wed 1/10

4:40 p.m.-5:33 p.m.

Nonstop1h 53m

C$ 237

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 18/9

9:31 p.m.-10:04 a.m.

1 stop11h 33m

Toronto Pearson Intl

Wed 24/9

5:15 p.m.-6:12 p.m.

Nonstop1h 57m

C$ 242

ChicagoEdmonton

ORD - YEG

ORDYEG

Chicago O'Hare Intl

Mon 25/8

5:30 p.m.-12:27 a.m.

1 stop7h 57m

Edmonton

Wed 27/8

8:00 a.m.-4:44 p.m.

1 stop7h 44m

C$ 245

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 22/6

8:45 a.m.-11:38 a.m.

Nonstop3h 53m

Calgary

Sat 28/6

6:15 a.m.-8:03 p.m.

1 stop12h 48m

C$ 269

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 24/6

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

Toronto Island

Thu 26/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

C$ 269

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 22/9

3:35 p.m.-11:16 p.m.

1 stop8h 41m

Calgary

Mon 29/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

C$ 276

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 15/7

6:00 a.m.-12:05 p.m.

1 stop5h 05m

Toronto Pearson Intl

Tue 15/7

3:45 p.m.-9:31 p.m.

1 stop6h 46m

C$ 282

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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$ 167). Flying from Chicago to Canada in July is currently the most expensive (average of C$ 255). 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 12 June 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 12 June 2025.

The most flights from CHI to CA0 are scheduled on a Thursday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 12 June 2025.
Get a feel of what it's like to fly with Japan Airlines, Delta and Alaska 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
1,490 reviews
Check prices

Crew

8.7

Overall

8.3

Food

7.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,May 2025

DFW - NRT

This flight was operated by American Airlines. The food was barely tolerable. Mid flight sandwich was ice cold, could not be bothered to warm it up. Staff did not seem to like their jobs very much. Too many seats packed in to maximize profit. A true “cattle car” experience. Subsequent flight from Tokyo to HCMC was on Japan Airlines which was excellent. No comparison between JAL and AA. Unfortunately that’s just the way service is in America nowadays.
Japan Airlines
8.3
Very good
1,490 reviews
Japan Airlines
8.3
Very good
1,490 reviews
Check prices

Crew

8.7

Overall

8.3

Food

7.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,May 2025

DFW - NRT

This flight was operated by American Airlines. The food was barely tolerable. Mid flight sandwich was ice cold, could not be bothered to warm it up. Staff did not seem to like their jobs very much. Too many seats packed in to maximize profit. A true “cattle car” experience. Subsequent flight from Tokyo to HCMC was on Japan Airlines which was excellent. No comparison between JAL and AA. Unfortunately that’s just the way service is in America nowadays.
Delta
8.0
Very good
7,946 reviews
Japan Airlines
8.3
Very good
1,490 reviews
Check prices

Crew

8.7

Overall

8.3

Food

7.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,May 2025

DFW - NRT

This flight was operated by American Airlines. The food was barely tolerable. Mid flight sandwich was ice cold, could not be bothered to warm it up. Staff did not seem to like their jobs very much. Too many seats packed in to maximize profit. A true “cattle car” experience. Subsequent flight from Tokyo to HCMC was on Japan Airlines which was excellent. No comparison between JAL and AA. Unfortunately that’s just the way service is in America nowadays.
Alaska Airlines
8.0
Very good
10,000 reviews
Japan Airlines
8.3
Very good
1,490 reviews
Check prices

Crew

8.7

Overall

8.3

Food

7.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,May 2025

DFW - NRT

This flight was operated by American Airlines. The food was barely tolerable. Mid flight sandwich was ice cold, could not be bothered to warm it up. Staff did not seem to like their jobs very much. Too many seats packed in to maximize profit. A true “cattle car” experience. Subsequent flight from Tokyo to HCMC was on Japan Airlines which was excellent. No comparison between JAL and AA. Unfortunately that’s just the way service is in America nowadays.
Porter Airlines
8.0
Very good
288 reviews
Japan Airlines
8.3
Very good
1,490 reviews
Check prices

Crew

8.7

Overall

8.3

Food

7.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,May 2025

DFW - NRT

This flight was operated by American Airlines. The food was barely tolerable. Mid flight sandwich was ice cold, could not be bothered to warm it up. Staff did not seem to like their jobs very much. Too many seats packed in to maximize profit. A true “cattle car” experience. Subsequent flight from Tokyo to HCMC was on Japan Airlines which was excellent. No comparison between JAL and AA. Unfortunately that’s just the way service is in America nowadays.
Air Transat
7.8
Good
396 reviews
Japan Airlines
8.3
Very good
1,490 reviews
Check prices

Crew

8.7

Overall

8.3

Food

7.7

Comfort

8.2

Entertainment

7.8

Boarding

8.4

Reviews

1 / 20
6.0
Good

Anonymous,May 2025

DFW - NRT

This flight was operated by American Airlines. The food was barely tolerable. Mid flight sandwich was ice cold, could not be bothered to warm it up. Staff did not seem to like their jobs very much. Too many seats packed in to maximize profit. A true “cattle car” experience. Subsequent flight from Tokyo to HCMC was on Japan Airlines which was excellent. No comparison between JAL and AA. Unfortunately that’s just the way service is in America nowadays.

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 American Airlines, with whom users have recently found tickets for as low as C$ 100. However, be on the lookout for offers from WestJet and United 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 - Toronto Pearson 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: Royal Jordanian (97%), SkyWest Airlines (94%), Korean Air( 93%).

  • 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$ 304, our data indicates the cheapest price to be C$ 111. The most popular route (Chicago O'Hare Intl - Vancouver Intl), is priced around C$ 349.

  • 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$ 167). Flying from Chicago to Canada in July is currently the most expensive (average of C$ 255). 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.
O'Hare Intl to Vancouver Intl flights
O'Hare Intl to Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Calgary flights
Midway to Toronto Island flights
Midway to Pearson Intl flights
Midway to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Edmonton flights
St. Louis to Pearson Intl flights
O'Hare Intl to Québec City flights
O'Hare Intl to Toronto Island flights
O'Hare Intl to Ottawa flights
St. Louis to Vancouver Intl flights
St. Louis to Pierre Elliott Trudeau Intl flights
St. Louis to Calgary flights
O'Hare Intl to Abbotsford flights
Midway to Québec City flights
O'Hare Intl to Halifax flights
O'Hare Intl to Winnipeg flights
Midway to Ottawa flights
O'Hare Intl to Victoria flights
O'Hare Intl to St. John's flights
St. Louis to Edmonton flights
O'Hare Intl to Kelowna flights
O'Hare Intl to Saskatoon flights
O'Hare Intl to Charlottetown flights
St. Louis to Halifax flights
O'Hare Intl to Hamilton flights
O'Hare Intl to Nanaimo flights
Midway to Kelowna flights
St. Louis to Québec City flights
St. Louis to Saskatoon flights
O'Hare Intl to Regina flights
O'Hare Intl to San Francisco flights
Evansville to Pearson Intl flights
St. Louis to Charlottetown flights
O'Hare Intl to Los Angeles flights

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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 126AverageC$ 716FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 142AverageC$ 300FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 211AverageC$ 489FlexibilityNo cancel feeOn-time69%
Search United 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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