Find flights
Deals
When to book
Airlines
FAQs

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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
19 Aug — 26 Aug1
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 14 August 2025.

Round-trip from

C$ 203

One-way from

C$ 146

Popular in

December

Cheapest in

July

Average price

C$ 356

Good round-trip deal

C$ 216 or less

Good one-way deal

C$ 128 or less
Air Canada
  • Air Canada
  • 6/11-10/11
  • Nonstop
  • 3h 34m total
  • Canada to Chicago
Search Deals
American Airlines
  • American Airlines
  • 14/11
  • Nonstop
  • 2h 00m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals
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).
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 14 August 2025.

Thu 6/112:15 p.m.YYZ - ORD
Nonstop1h 55mAir Canada
Mon 10/113:55 p.m.ORD - YYZ
Nonstop1h 39mAir Canada
Deal found 13/8C$ 203
Fri 7/119:00 p.m.YYZ - ORD
Nonstop2h 05mUnited Airlines
Mon 10/119:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 12/8C$ 204
Sat 1/115:30 p.m.YYZ - ORD
Nonstop2h 09mUnited Airlines
Fri 7/119:20 p.m.ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 12/8C$ 208
Sun 12/102:10 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 30/118:00 a.m.ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 14/8C$ 219
Thu 2/106:35 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sun 5/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 13/8C$ 222
Thu 2/104:40 p.m.YYZ - ORD
Nonstop1h 53mAir Canada
Mon 6/108:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 12/8C$ 225
Tue 30/912:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Sat 4/101:40 p.m.ORD - YYC
1 stop6h 00mWestJet
Deal found 12/8C$ 227
Wed 1/1012:20 p.m.YYZ - ORD
Nonstop1h 54mAir Canada
Sat 4/103:50 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 14/8C$ 229
Tue 30/96:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Tue 21/109:45 p.m.ORD - YYC
1 stop15h 14mAmerican Airlines
Deal found 12/8C$ 229
Mon 8/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Tue 16/98:40 a.m.ORD - YYC
1 stop8h 10mAir Canada
Deal found 12/8C$ 230
Fri 12/98:20 a.m.YUL - ORD
Nonstop2h 31mAir Canada
Sun 14/910:40 a.m.ORD - YUL
Nonstop2h 14mAir Canada
Deal found 13/8C$ 232
Sat 20/98:20 a.m.YUL - ORD
Nonstop2h 31mAir Canada
Sun 21/98:40 a.m.ORD - YUL
Nonstop2h 17mAir Canada
Deal found 14/8C$ 233

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 14 August 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

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 1/11

8:55 a.m.-10:00 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sat 8/11

1:19 p.m.-4:02 p.m.

Nonstop1h 43m

C$ 208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/10

2:15 p.m.-3:10 p.m.

Nonstop1h 55m

Chicago O'Hare Intl

Thu 6/11

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/11

7:40 p.m.-11:43 p.m.

1 stop5h 03m

Chicago O'Hare Intl

Mon 10/11

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 223

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 30/9

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

Nonstop3h 28m

Chicago O'Hare Intl

Sat 4/10

1:40 p.m.-6:40 p.m.

1 stop6h 00m

C$ 227

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 30/9

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

Tue 21/10

9:45 p.m.-11:59 a.m.

1 stop15h 14m

C$ 229

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/10

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

Nonstop1h 54m

Chicago O'Hare Intl

Sun 5/10

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

Nonstop1h 43m

C$ 229

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 24/9

6:15 a.m.-9:32 p.m.

1 stop14h 17m

Chicago O'Hare Intl

Sat 4/10

2:53 p.m.-9:48 p.m.

1 stop7h 55m

C$ 230

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 8/9

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

1 stop7h 41m

Chicago O'Hare Intl

Tue 16/9

8:40 a.m.-3:50 p.m.

1 stop8h 10m

C$ 230

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

8:20 a.m.-9:51 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 5/10

10:40 a.m.-1:54 p.m.

Nonstop2h 14m

C$ 233

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 20/9

8:20 a.m.-9:51 a.m.

Nonstop2h 31m

Chicago O'Hare Intl

Sun 21/9

8:40 a.m.-11:57 a.m.

Nonstop2h 17m

C$ 233

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 60 results
1
2
3
...
6

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$ 352). 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 14 August 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 14 August 2025.

The most flights from CA0 to CHI are scheduled on a Thursday (61 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (40 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 14 August 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
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,916 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
3,015 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,949 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 American Airlines, which is currently one of the cheapest options available, starting at C$ 146. Porter Airlines flights start at C$ 146 while deals on Air Canada start at C$ 148 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 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: SkyWest Airlines (89%), Egyptair (87%), Copa Airlines( 87%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 194. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 203 on average our data indicates C$ 1,510 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$ 352). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Pearson Intl to Midway flights
Toronto Island to Midway flights
Vancouver Intl to O'Hare Intl flights
Pearson Intl to St. Louis flights
Québec City to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Calgary to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Ottawa to O'Hare Intl flights
Winnipeg to O'Hare Intl flights
Vancouver Intl to Midway flights
Québec City to Midway flights
Calgary to Midway flights
Ottawa to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Halifax to O'Hare Intl flights
Edmonton to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Edmonton to Midway flights
Region of Waterloo Intl to O'Hare Intl flights
Victoria to O'Hare Intl flights
Saskatoon to O'Hare Intl flights
Halifax to Midway flights
Edmonton to St. Louis flights
Saskatoon to Midway flights
Nanaimo to O'Hare Intl flights
Seattle to O'Hare Intl flights
Detroit to O'Hare Intl flights
Calgary to St. Louis flights
London to O'Hare Intl flights
Hamilton to O'Hare Intl flights
Regina to O'Hare Intl flights
Pearson Intl to Peoria flights
Vancouver Intl to St. Louis flights
St John to O'Hare Intl flights
Moncton to O'Hare Intl flights
Victoria to Midway flights
Pearson Intl to Bloomington flights
Comox to O'Hare Intl flights

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 14 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 149AverageC$ 501FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 177AverageC$ 450FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 184AverageC$ 477FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 185AverageC$ 453FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Porter AirlinesCheapestC$ 202AverageC$ 423FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 242AverageC$ 541FlexibilityNo 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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.