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Cheap flights from Canada to Chicago from C$ 136

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 17/10. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated 17 September 2025.

Round-trip from

C$ 205

One-way from

C$ 136

Popular in

December

Cheapest in

July

Average price

C$ 349

Good round-trip deal

C$ 240 or less

Good one-way deal

C$ 210 or less
WestJet
  • WestJet
  • 17/10-19/10
  • 2 total stops
  • 14h 49m total
  • Canada to Chicago
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WestJet
  • WestJet
  • 17/10
  • 1 total stop
  • 8h 43m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 7 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 Canada to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Canada to Chicago (CHI).
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Find flight deals from Canada to Chicago

Cheapest flights from Canada to Chicago
Explore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 September 2025.

Fri 17/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Sat 18/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 15/9C$ 205
Fri 17/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Sun 19/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 17/9C$ 208
Sun 12/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Sun 19/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 14/9C$ 210
Fri 3/106:00 a.m.YVR - ORD
1 stop8h 43mWestJet
Mon 6/105:30 p.m.ORD - YVR
1 stop8h 41mWestJet
Deal found 15/9C$ 212
Mon 27/109:00 a.m.YYC - ORD
Nonstop3h 35mWestJet
Fri 31/102:20 p.m.ORD - YYC
Nonstop3h 55mWestJet
Deal found 17/9C$ 213
Fri 17/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Sun 19/105:30 p.m.ORD - YVR
1 stop7h 06mWestJet
Deal found 16/9C$ 213
Fri 24/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Mon 27/102:20 p.m.ORD - YVR
1 stop7h 25mWestJet
Deal found 16/9C$ 216
Fri 17/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Thu 23/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 16/9C$ 220
Fri 17/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Mon 27/102:20 p.m.ORD - YVR
1 stop7h 25mWestJet
Deal found 14/9C$ 220
Thu 16/107:00 a.m.YVR - ORD
1 stop7h 43mWestJet
Thu 23/105:30 p.m.ORD - YVR
1 stop8h 41mWestJet
Deal found 15/9C$ 221
Thu 16/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Fri 17/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 16/9C$ 224
Thu 16/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Thu 23/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 16/9C$ 226

Cheapflights Fare Finder

 
Customize your flight search to find flights from Canada to Chicago 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 17 September 2025.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Canada

Fly to

Chicago

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 18/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Mon 20/10

7:41 p.m.-10:18 p.m.

Nonstop4h 37m

C$ 231

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 10/11

10:30 a.m.-4:44 p.m.

Nonstop4h 14m

Chicago O'Hare Intl

Thu 13/11

6:15 a.m.-1:39 p.m.

1 stop9h 24m

C$ 256

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 5/12

8:30 a.m.-11:59 p.m.

1 stop13h 29m

Chicago O'Hare Intl

Sun 7/12

3:40 p.m.-6:15 p.m.

Nonstop4h 35m

C$ 263

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 3/10

11:00 a.m.-8:25 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Mon 6/10

7:41 p.m.-10:18 p.m.

Nonstop4h 37m

C$ 263

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 17/10

12:38 p.m.-5:10 p.m.

Nonstop3h 32m

Chicago O'Hare Intl

Sun 19/10

5:01 a.m.-1:53 p.m.

1 stop9h 52m

C$ 271

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 14/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Thu 23/10

7:41 p.m.-10:18 p.m.

Nonstop4h 37m

C$ 271

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 14/11

10:30 a.m.-4:44 p.m.

Nonstop4h 14m

Chicago O'Hare Intl

Mon 17/11

7:10 a.m.-6:45 p.m.

1 stop13h 35m

C$ 271

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 16/10

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Wed 22/10

5:01 a.m.-9:51 a.m.

1 stop6h 50m

C$ 271

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 18/10

6:45 a.m.-3:00 p.m.

1 stop7h 15m

Chicago O'Hare Intl

Thu 23/10

8:57 a.m.-1:54 p.m.

1 stop5h 57m

C$ 308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 28/11

6:15 a.m.-11:59 p.m.

1 stop16h 44m

Chicago O'Hare Intl

Tue 2/12

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 308

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/9

Showing 1-10 of 60 results
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Best time to book a flight from Canada to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada 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 Canada to Chicago

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

Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 261). Flying from Canada to Chicago in March is currently the most expensive (average of C$ 348). 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 CA to CHI?

Find hourly flight availability from Canada to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 17 September 2025.

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

Weekly flight availability from Canada to Chicago

Explore weekly flight availability from Canada to Chicago. 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 17 September 2025.

The most flights from CA0 to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated 17 September 2025.
Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andAmerican Airlines from Canada to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.6

Comfort

7.9

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
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.6

Comfort

7.9

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
8,926 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.6

Comfort

7.9

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.
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.6

Comfort

7.9

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
3,095 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.6

Comfort

7.9

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

Boarding

8.2

Crew

8.6

Overall

7.9

Food

7.6

Comfort

7.9

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 Canada to Chicago. 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 Canada to Chicago?

    A quick flight from Canada to Chicago can take about 1h 49m. United Airlines provides one of the quickest options available for as low as C$ 330. Canada and Chicago are separated by a distance of 711 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 140. United Airlines flights start at C$ 142 while deals on American Airlines start at C$ 142 one-way.

  • What are the most popular routes from Canada to Chicago?

    When deciding which route to take from Canada to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Vancouver Intl - Chicago O'Hare Intl or Toronto Pearson Intl - Chicago Midway as they are the most popular.

  • What are the most reliable airlines from Canada to Chicago?

    Before booking your flight to Chicago from Canada, check out the most reliable airlines to get you to your destination on time: EVA Air (88%), Egyptair (85%), Copa Airlines( 85%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 239. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 316 on average, our data indicates C$ 1,696 when flying from Canada to Chicago.

  • Can I find deals for flights from Canada to Chicago that include hotel bookings?

    Yes. In addition to deals on Canada to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Chicago.

  • Can I find deals for business class flights from Canada to Chicago?

    Yes. Cheapflights offers flight deals from Canada to Chicago 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 Canada to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 261). Flying from Canada to Chicago in March is currently the most expensive (average of C$ 348). 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 Canada to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Canada to Chicago

Discover the top 6 airlines that operate flights from Canada to Chicago. 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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 149AverageC$ 497FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 176AverageC$ 451FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 177AverageC$ 439FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapestC$ 183AverageC$ 474FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Porter AirlinesCheapestC$ 195AverageC$ 372FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 208AverageC$ 520FlexibilityNo 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 Canada to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Canada to Chicago. 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 Canada to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Canada to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Canada to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Canada shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Canada to Chicago become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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