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Cheap flights from Canada to Chicago from C$ 146

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 18/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
26 Feb — 5 Mar1
1 adult

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 21 February 2025.

Round-trip from

C$ 236

One-way from

C$ 146

Popular in

December

Cheapest in

April

Average price

C$ 405

Good round-trip deal

C$ 261 or less

Good one-way deal

C$ 175 or less
WestJet
  • WestJet
  • 13/5-21/5
  • Nonstop
  • 7h 18m total
  • Canada to Chicago
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WestJet
  • WestJet
  • 18/5
  • Nonstop
  • 3h 29m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 21 February 2025.

Tue 13/512:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Wed 21/55:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 19/2C$ 236
Thu 27/38:30 a.m.YYC - ORD
1 stop9h 11mAir Canada
Tue 1/410:53 a.m.ORD - YYC
1 stop10h 30mAir Canada
Deal found 20/2C$ 251
Thu 20/32:01 p.m.YYC - ORD
1 stop7h 44mUnited Airlines
Thu 27/35:00 a.m.ORD - YYC
1 stop10h 21mUnited Airlines
Deal found 20/2C$ 268
Wed 2/43:55 p.m.YVR - MDW
1 stop11h 28mMultiple Airlines
Tue 8/48:50 p.m.MDW - YVR
1 stop27h 40mMultiple Airlines
Deal found 20/2C$ 284
Sat 24/54:00 p.m.YYZ - ORD
1 stop5h 12mAir Canada
Sat 7/610:40 a.m.ORD - YYZ
1 stop6h 18mAir Canada
Deal found 20/2C$ 290
Sat 24/510:25 a.m.YTZ - ORD
1 stop5h 30mAir Canada
Sat 7/610:40 a.m.ORD - YTZ
1 stop6h 10mAir Canada
Deal found 20/2C$ 290
Wed 19/33:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 22/312:55 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 20/2C$ 294
Wed 11/67:00 a.m.YVR - ORD
1 stop7h 44mWestJet
Wed 18/61:40 p.m.ORD - YVR
1 stop7h 30mWestJet
Deal found 20/2C$ 300
Mon 28/43:55 p.m.YVR - ORD
1 stop12h 38mMultiple Airlines
Tue 29/49:04 p.m.ORD - YVR
2 stops27h 21mMultiple Airlines
Deal found 20/2C$ 310
Tue 13/57:15 a.m.YYC - ORD
1 stop9h 46mDelta
Sat 17/59:30 a.m.ORD - YYC
2 stops14h 37mDelta
Deal found 20/2C$ 312
Thu 13/39:00 p.m.YYZ - ORD
Nonstop2h 06mMultiple Airlines
Thu 10/47:10 a.m.ORD - YYZ
Nonstop1h 48mMultiple Airlines
Deal found 19/2C$ 315
Tue 13/55:30 p.m.YYC - ORD
1 stop17h 38mMultiple Airlines
Sun 18/55:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 19/2C$ 325

Find flights from Canada to Chicago within your budget

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 21 February 2025.

Fly from

Canada

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 13/5

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

Nonstop3h 29m

Chicago O'Hare Intl

Wed 21/5

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

Nonstop3h 49m

C$ 236

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 27/3

8:30 a.m.-6:41 p.m.

1 stop9h 11m

Chicago O'Hare Intl

Tue 1/4

10:53 a.m.-8:23 p.m.

1 stop10h 30m

C$ 251

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 20/3

2:01 p.m.-10:45 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Thu 27/3

5:00 a.m.-2:21 p.m.

1 stop10h 21m

C$ 268

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 2/4

3:55 p.m.-5:23 a.m.

1 stop11h 28m

Chicago Midway

Tue 8/4

8:50 p.m.-10:30 p.m.

1 stop27h 40m

C$ 284

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 24/5

4:00 p.m.-8:12 p.m.

1 stop5h 12m

Chicago O'Hare Intl

Sat 7/6

10:40 a.m.-5:58 p.m.

1 stop6h 18m

C$ 290

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 24/5

10:25 a.m.-2:55 p.m.

1 stop5h 30m

Chicago O'Hare Intl

Sat 7/6

10:40 a.m.-5:50 p.m.

1 stop6h 10m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 19/3

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

Nonstop1h 50m

Chicago Midway

Sat 22/3

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

Nonstop1h 42m

C$ 294

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 11/6

7:00 a.m.-4:44 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Wed 18/6

1:40 p.m.-7:10 p.m.

1 stop7h 30m

C$ 300

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 28/4

3:55 p.m.-6:33 a.m.

1 stop12h 38m

Chicago O'Hare Intl

Tue 29/4

9:04 p.m.-10:25 p.m.

2 stops27h 21m

C$ 310

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 13/5

7:15 a.m.-6:01 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Sat 17/5

9:30 a.m.-11:07 p.m.

2 stops14h 37m

C$ 312

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/2

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.

Travel insights for flights from Canada to Chicago

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

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$ 355). 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 21 February 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 21 February 2025.

The most flights from CA0 to CHI are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 21 February 2025.
See what other customers who have flown with Alaska Airlines, Delta and Porter Airlines from Canada to Chicago have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,697 reviews
Check prices

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,697 reviews
Alaska Airlines
8.0
Very good
9,697 reviews
Check prices

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,219 reviews
Alaska Airlines
8.0
Very good
9,697 reviews
Check prices

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Porter Airlines
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,697 reviews
Check prices

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

KLM
7.8
Good
1,333 reviews
Alaska Airlines
8.0
Very good
9,697 reviews
Check prices

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Air Transat
7.8
Good
380 reviews
Alaska Airlines
8.0
Very good
9,697 reviews
Check prices

Comfort

7.9

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

  • 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$ 146. United Airlines flights start at C$ 149 while deals on Air Canada start at C$ 156 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: Emirates (90%), Republic Airways (89%), ANA( 84%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 189. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 304 on average our data indicates C$ 1,415 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$ 355). 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 8 airlines flying from Canada to Chicago

Discover the top 8 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 21 February 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 189AverageC$ 586FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 201AverageC$ 483FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 239AverageC$ 565FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 249AverageC$ 574FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 267AverageC$ 453FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
DeltaCheapestC$ 291AverageC$ 539FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Alaska AirlinesCheapestC$ 369AverageC$ 617FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
WestJet EncoreCheapestC$ 572AverageC$ 1,011FlexibilityNo cancel feeOn-timeN/A
Search WestJet Encore 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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