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Cheap flights from Canada to Chicago from C$ 124

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 13/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
26 Dec — 2 Jan1
1 adult

Cheap flight deals from Canada to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Canada (CA0) to Chicago (CHI). 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 December 2024.

Round-trip from

C$ 258

One-way from

C$ 124
Air Canada
  • Air Canada
  • 8/1-14/1
  • 2 total stops
  • 17h 47m total
  • Canada to Chicago
Search Deals
WestJet
  • WestJet
  • 13/3
  • Nonstop
  • 3h 26m total
  • Canada to Chicago
Search Deals

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 December 2024.

Thu 26/126:29 a.m.YYC - ORD
1 stop15h 40mAmerican Airlines
Wed 1/17:09 a.m.ORD - YYC
1 stop15h 46mAmerican Airlines
Deal found 21/12C$ 434
Mon 30/123:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 3/15:35 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/12C$ 459
Mon 23/1210:40 p.m.YVR - ORD
1 stop8h 17mAir Canada
Tue 24/1212:56 p.m.ORD - YVR
1 stop7h 30mAir Canada
Deal found 20/12C$ 492
Mon 30/126:50 a.m.YUL - MDW
1 stop5h 20mPorter Airlines
Mon 13/11:05 p.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 20/12C$ 525
Sun 29/1212:20 p.m.YYZ - ORD
Nonstop1h 51mUnited Airlines
Wed 1/19:13 p.m.ORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 18/12C$ 544
Sat 28/129:40 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sat 4/15:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 20/12C$ 561
Fri 27/1212:20 p.m.YYZ - ORD
Nonstop1h 51mMultiple Airlines
Fri 3/16:06 p.m.ORD - YYZ
1 stop12h 59mMultiple Airlines
Deal found 20/12C$ 564
Mon 30/128:00 a.m.YYZ - ORD
Nonstop1h 57mAir Canada
Thu 2/16:28 p.m.ORD - YYZ
Nonstop1h 57mAir Canada
Deal found 19/12C$ 578
Mon 30/123:30 p.m.YVR - ORD
1 stop6h 29mUnited Airlines
Tue 18/28:45 a.m.ORD - YVR
1 stop11h 18mUnited Airlines
Deal found 20/12C$ 578
Mon 23/121:30 p.m.YYC - ORD
1 stop8h 50mMultiple Airlines
Fri 3/18:30 p.m.ORD - YYC
1 stop17h 23mMultiple Airlines
Deal found 19/12C$ 591
Fri 27/1210:25 a.m.YTZ - ORD
1 stop5h 20mAir Canada
Fri 3/12:01 p.m.ORD - YTZ
1 stop4h 49mAir Canada
Deal found 20/12C$ 603
Tue 24/1212:55 a.m.YYC - ORD
1 stop8h 59mAir Canada
Sun 5/112:56 p.m.ORD - YYC
1 stop11h 22mAir Canada
Deal found 21/12C$ 611

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 December 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 8/1

12:50 a.m.-10:10 a.m.

1 stop8h 20m

Chicago O'Hare Intl

Tue 14/1

12:51 p.m.-9:18 p.m.

1 stop9h 27m

C$ 258

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 17/3

7:20 p.m.-9:33 a.m.

1 stop13h 13m

Chicago O'Hare Intl

Tue 18/3

12:58 p.m.-11:18 p.m.

1 stop11h 20m

C$ 260

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 29/5

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

Nonstop3h 29m

Chicago O'Hare Intl

Sun 1/6

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

Nonstop3h 49m

C$ 299

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/1

6:35 a.m.-5:29 p.m.

1 stop9h 54m

Chicago O'Hare Intl

Sat 18/1

9:46 a.m.-8:53 p.m.

2 stops12h 07m

C$ 311

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/1

12:20 p.m.-6:38 p.m.

1 stop7h 18m

Chicago O'Hare Intl

Sat 18/1

7:20 a.m.-2:41 p.m.

1 stop6h 21m

C$ 331

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 13/2

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

Nonstop1h 50m

Chicago Midway

Sun 16/2

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

Nonstop1h 42m

C$ 335

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 15/1

10:00 a.m.-11:32 p.m.

1 stop14h 32m

Chicago O'Hare Intl

Tue 21/1

5:11 a.m.-11:55 p.m.

1 stop17h 44m

C$ 337

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 18/1

6:15 a.m.-7:30 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sun 19/1

9:49 a.m.-12:30 p.m.

Nonstop1h 41m

C$ 338

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/1

9:00 p.m.-10:13 p.m.

Nonstop2h 13m

Chicago O'Hare Intl

Sun 12/1

7:05 a.m.-9:58 a.m.

Nonstop1h 53m

C$ 344

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/1

9:00 a.m.-10:10 a.m.

Nonstop2h 10m

Chicago O'Hare Intl

Sun 12/1

7:05 a.m.-9:58 a.m.

Nonstop1h 53m

C$ 350

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/12

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 December 2024.

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 December 2024.

The most flights from CA0 to CHI are scheduled on a Thursday (54 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (36 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 December 2024.
See what other customers who have flown with Air Canada, WestJet and Delta 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.
Delta
8.0
Very good
8,597 reviews
Check prices

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,597 reviews
Delta
8.0
Very good
8,597 reviews
Check prices

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Alaska Airlines
8.0
Very good
9,540 reviews
Delta
8.0
Very good
8,597 reviews
Check prices

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
283 reviews
Delta
8.0
Very good
8,597 reviews
Check prices

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,344 reviews
Delta
8.0
Very good
8,597 reviews
Check prices

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
384 reviews
Delta
8.0
Very good
8,597 reviews
Check prices

Entertainment

7.9

Crew

8.6

Comfort

8.0

Food

7.3

Overall

8.0

Boarding

8.2

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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$ 124. Air Canada flights start at C$ 140 while deals on United Airlines start at C$ 174 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, Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Vancouver Intl - Chicago O'Hare Intl 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: Lufthansa (100%), Royal Jordanian (97%), SkyWest Airlines( 97%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 223. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 352 on average our data indicates C$ 1,465 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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Kelowna to Midway flights
Calgary to St. Louis flights
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Pierre Elliott Trudeau Intl to St. Louis flights
Pearson Intl to Moline flights
Victoria to O'Hare Intl flights
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London to O'Hare Intl flights
Edmonton to St. Louis flights
Buffalo to O'Hare Intl flights
Ottawa to St. Louis flights
Fort McMurray to O'Hare Intl flights

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 December 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 204AverageC$ 478FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 240AverageC$ 628FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 279AverageC$ 452FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 295AverageC$ 592FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 318AverageC$ 525FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 331AverageC$ 590FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Alaska AirlinesCheapestC$ 374AverageC$ 647FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
WestJet EncoreCheapestC$ 580AverageC$ 1,023FlexibilityNo 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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