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Cheap flights from Chicago to Canada from C$ 97

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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
5 Aug — 12 Aug1
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 31 July 2025.

Round-trip from

C$ 215

One-way from

C$ 97

Popular in

November

Cheapest in

August

Average price

C$ 372

Good round-trip deal

C$ 114 or less

Good one-way deal

C$ 114 or less
WestJet
  • WestJet
  • 15/9-24/9
  • Nonstop
  • 7h 17m total
  • Chicago to Canada
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Air Transat
  • Air Transat
  • 4/9
  • Nonstop
  • 1h 42m total
  • Chicago to Canada
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 31 July 2025.

Mon 15/95:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Wed 24/912:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 29/7C$ 215
Mon 15/93:50 p.m.ORD - YYC
1 stop8h 32mMultiple Airlines
Wed 24/912:15 p.m.YYC - ORD
Nonstop3h 28mMultiple Airlines
Deal found 29/7C$ 218
Mon 15/96:20 p.m.ORD - YYC
1 stop7h 52mAir Canada
Tue 23/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Deal found 29/7C$ 221
Sun 7/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 12/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 29/7C$ 237
Sat 13/98:50 a.m.ORD - YYZ
1 stop4h 29mUnited Airlines
Sat 13/95:15 p.m.YYZ - ORD
Nonstop1h 57mUnited Airlines
Deal found 30/7C$ 239
Fri 12/98:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Mon 15/92:10 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Deal found 30/7C$ 244
Wed 5/118:45 a.m.ORD - YYC
Nonstop3h 50mUnited Airlines
Tue 11/1112:37 p.m.YYC - ORD
Nonstop3h 33mUnited Airlines
Deal found 30/7C$ 250
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Fri 12/93:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Deal found 29/7C$ 254
Wed 20/89:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Sat 30/89:00 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 27/7C$ 261
Wed 24/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Fri 26/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Deal found 28/7C$ 270
Sat 20/912:33 p.m.ORD - YUL
1 stop8h 59mMultiple Airlines
Mon 22/98:20 a.m.YUL - ORD
Nonstop2h 31mMultiple Airlines
Deal found 30/7C$ 274
Wed 10/98:15 a.m.ORD - YYZ
Nonstop1h 44mAmerican Airlines
Sat 13/911:44 a.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
Deal found 30/7C$ 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 31 July 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

Mon 15/9

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

Nonstop3h 49m

Calgary

Wed 24/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 215

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

3:50 p.m.-11:22 p.m.

1 stop8h 32m

Calgary

Wed 24/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 218

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

6:20 p.m.-1:12 a.m.

1 stop7h 52m

Calgary

Tue 23/9

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

1 stop7h 41m

C$ 221

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 7/9

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

Nonstop1h 42m

Toronto Island

Fri 12/9

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

Nonstop1h 49m

C$ 237

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 13/9

8:50 a.m.-2:19 p.m.

1 stop4h 29m

Toronto Pearson Intl

Sat 13/9

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

Nonstop1h 57m

C$ 239

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 12/9

8:25 p.m.-11:08 p.m.

Nonstop1h 43m

Toronto Pearson Intl

Mon 15/9

2:10 p.m.-3:04 p.m.

Nonstop1h 54m

C$ 244

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$ 250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/9

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

Nonstop1h 42m

Toronto Island

Fri 12/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 254

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 20/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

Toronto Island

Sat 30/8

9:00 a.m.-9:50 a.m.

Nonstop1h 50m

C$ 261

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 24/9

5:20 p.m.-10:15 p.m.

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Fri 26/9

1:10 p.m.-4:24 p.m.

1 stop4h 14m

C$ 270

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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$ 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 31 July 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 31 July 2025.

The most flights from CHI to CA0 are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 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 31 July 2025.
Get a feel of what it's like to fly with Alaska Airlines,Porter Airlines, andDelta 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.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Porter Airlines
8.0
Very good
318 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Air Transat
7.7
Good
424 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Finnair
7.6
Good
1,316 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 Air Transat, with whom users have recently found tickets for as low as C$ 97. However, be on the lookout for offers from Air Canada 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 - Toronto Pearson Intl, Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau 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: SkyWest Airlines (91%), Envoy Air (84%), Japan 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$ 210, our data indicates the cheapest price to be C$ 92. The most popular route (Chicago O'Hare Intl - Toronto Pearson Intl), is priced around C$ 219.

  • 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$ 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

Browse thousands of different options on Cheapflights for your next trip

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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 Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
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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 31 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 203AverageC$ 751FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 211AverageC$ 392FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 243AverageC$ 447FlexibilityNo 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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