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Cheap flights from Canada to Chicago from C$ 148

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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
25 Nov — 2 Dec1
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 20 November 2024.

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 20 November 2024.

Tue 26/118:30 a.m.YYC - ORD
1 stop9h 06mAir Canada
Sat 30/1112:52 p.m.ORD - YYC
1 stop9h 26mAir Canada
Deal found 19/11C$ 307
Sat 7/127:00 a.m.YYC - ORD
2 stops13h 12mDelta
Tue 10/128:35 a.m.ORD - YYC
2 stops13h 03mDelta
Deal found 19/11C$ 308
Thu 12/123:50 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 16/1212:05 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 319
Wed 11/1212:00 p.m.YYZ - ORD
1 stop7h 41mAir Canada
Thu 12/127:19 a.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 18/11C$ 332
Sat 14/128:25 a.m.YTZ - ORD
1 stop7h 20mAir Canada
Fri 10/111:35 a.m.ORD - YTZ
1 stop5h 15mAir Canada
Deal found 18/11C$ 337
Wed 11/1211:00 a.m.YYZ - ORD
Nonstop1h 59mUnited Airlines
Thu 12/127:19 a.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 19/11C$ 343
Thu 12/126:15 a.m.YYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 15/128:05 a.m.ORD - YYZ
1 stop9h 19mAmerican Airlines
Deal found 18/11C$ 357
Thu 12/126:25 a.m.YYZ - ORD
1 stop5h 29mMultiple Airlines
Sun 15/127:19 a.m.ORD - YYZ
Nonstop1h 39mMultiple Airlines
Deal found 19/11C$ 363
Thu 12/123:50 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 15/125:35 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 19/11C$ 364
Thu 12/1212:20 p.m.YYZ - ORD
Nonstop1h 51mLufthansa
Sun 15/127:19 a.m.ORD - YYZ
Nonstop1h 39mLufthansa
Deal found 19/11C$ 367
Thu 12/126:30 a.m.YYZ - MDW
1 stop13h 02mWestJet
Mon 16/129:38 a.m.MDW - YYZ
1 stop12h 56mWestJet
Deal found 20/11C$ 374
Tue 3/1211:15 a.m.YUL - ORD
1 stop4h 36mAir Canada
Wed 4/122:00 p.m.ORD - YUL
1 stop6h 48mAir Canada
Deal found 18/11C$ 375

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 645,034 searches. Data last updated 20 November 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/4

8:30 a.m.-12:49 p.m.

Nonstop3h 19m

Chicago O'Hare Intl

Tue 15/4

9:03 a.m.-4:52 p.m.

1 stop8h 49m

C$ 294

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 7/12

7:00 a.m.-2:39 p.m.

1 stop6h 39m

Chicago O'Hare Intl

Tue 10/12

12:35 p.m.-11:16 p.m.

2 stops11h 41m

C$ 307

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/4

11:30 a.m.-3:56 p.m.

Nonstop3h 26m

Chicago O'Hare Intl

Tue 15/4

7:45 p.m.-10:29 p.m.

Nonstop3h 44m

C$ 311

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

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

Nonstop1h 50m

Chicago Midway

Mon 16/12

12:05 p.m.-2:47 p.m.

Nonstop1h 42m

C$ 319

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/12

12:00 p.m.-6:41 p.m.

1 stop7h 41m

Chicago O'Hare Intl

Thu 12/12

7:19 a.m.-9:58 a.m.

Nonstop1h 39m

C$ 332

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 14/12

8:25 a.m.-2:45 p.m.

1 stop7h 20m

Chicago O'Hare Intl

Fri 10/1

11:35 a.m.-5:50 p.m.

1 stop5h 15m

C$ 337

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/12

11:00 a.m.-11:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Thu 12/12

7:19 a.m.-9:58 a.m.

Nonstop1h 39m

C$ 343

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

6:25 a.m.-10:54 a.m.

1 stop5h 29m

Chicago O'Hare Intl

Sun 15/12

7:19 a.m.-9:58 a.m.

Nonstop1h 39m

C$ 363

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

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

Nonstop1h 50m

Chicago Midway

Sun 15/12

5:35 p.m.-8:17 p.m.

Nonstop1h 42m

C$ 364

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

12:20 p.m.-1:11 p.m.

Nonstop1h 51m

Chicago O'Hare Intl

Sun 15/12

7:19 a.m.-9:58 a.m.

Nonstop1h 39m

C$ 367

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/11

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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 May is currently the most expensive (average of C$ 342). 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 20 November 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 20 November 2024.

The most flights from CA0 to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 20 November 2024.
See what other customers who have flown with Air Canada, Delta and American 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
9,461 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Alaska Airlines
8.0
Very good
9,461 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Delta
8.0
Very good
8,756 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

KLM
7.8
Good
1,350 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Porter Airlines
7.8
Good
288 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Air Transat
7.8
Good
389 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

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$ 148. Air Canada flights start at C$ 164 while deals on United Airlines start at C$ 179 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: Egyptair (100%), Jazz (100%), Lufthansa( 100%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 211. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 336 on average our data indicates C$ 1,606 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 May is currently the most expensive (average of C$ 342). 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.
Pearson Intl to O'Hare Intl flights
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Vancouver Intl to O'Hare Intl flights
Toronto Island to Midway flights
Pearson Intl to Midway flights
Pierre Elliott Trudeau Intl to Midway flights
Ottawa to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Vancouver Intl to Midway flights
Calgary to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Pearson Intl to St. Louis flights
Ottawa to Midway flights
Calgary to Midway flights
Halifax to O'Hare Intl flights
Calgary to St. Louis flights
Edmonton to O'Hare Intl flights
Québec City to O'Hare Intl flights
Halifax to Midway flights
Edmonton to Midway flights
Québec City to Midway flights
Buffalo to O'Hare Intl flights
Kelowna to O'Hare Intl flights
Victoria to O'Hare Intl flights
Detroit to O'Hare Intl flights
Pierre Elliott Trudeau Intl to St. Louis flights
Vancouver Intl to St. Louis flights
Saskatoon to O'Hare Intl flights
London to O'Hare Intl flights
Edmonton to St. Louis flights
Kelowna to Midway flights
St. John's to O'Hare Intl flights
Saskatoon to Midway flights
Victoria to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Ottawa to St. Louis flights
Regina to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Saskatoon to St. Louis flights
Pearson Intl to Moline flights
Moncton to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Québec City to St. Louis 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 645,034 searches. Data last updated 20 November 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 198AverageC$ 463FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 234AverageC$ 594FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 271AverageC$ 430FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 284AverageC$ 570FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 310AverageC$ 512FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 322AverageC$ 576FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Alaska AirlinesCheapestC$ 364AverageC$ 630FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
WestJet EncoreCheapestC$ 564AverageC$ 996FlexibilityNo 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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