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Cheap flights from Canada to Chicago from C$ 152

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 14/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
19 Apr — 26 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

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 March 2026.

Thu 7/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 11/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 17/3C$ 233
Fri 1/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 3/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 17/3C$ 236
Fri 1/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 4/53:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 16/3C$ 239
Thu 7/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 10/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 16/3C$ 240
Thu 23/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 16/3C$ 242
Fri 8/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 10/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 16/3C$ 244
Sun 26/49:50 a.m.
YUL
-
MDW
1 stop6h 30m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 18/3C$ 250
Fri 29/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 1/610:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 17/3C$ 259
Fri 1/56:30 p.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Fri 8/58:45 a.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 17/3C$ 261
Mon 1/66:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 8/63:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 18/3C$ 261
Tue 21/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 28/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 18/3C$ 264
Thu 9/49:15 a.m.
YUL
-
ORD
Nonstop2h 38m
Air Canada
Sun 12/412:50 p.m.
ORD
-
YUL
Nonstop2h 15m
Air Canada
Deal found 17/3C$ 264

Find flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated 20 March 2026.

Round-trip from

C$ 233

One-way from

C$ 152

Popular in

December

Cheapest in

July

Average price

C$ 371

Good round-trip deal

C$ 278 or less

Good one-way deal

C$ 215 or less
Porter Airlines
  • Porter Airlines
  • 7/5-11/5
  • 2 total stops
  • 10h 00m total
  • Canada to Chicago
Search Deals
Air Canada
  • Air Canada
  • 14/5
  • Nonstop
  • 2h 38m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 32 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 March 2026
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

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 20 March 2026.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 4/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/6

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 10/6

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 303

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 13/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Mon 20/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 306

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 30/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 2/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 308

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 28/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Wed 29/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 308

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 3/5

2:15 p.m.-8:40 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Sun 10/5

8:42 a.m.-6:31 p.m.

1 stop8h 49m

C$ 309

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sun 3/5

6:10 a.m.-8:47 a.m.

1 stop3h 37m

Chicago Midway

Sun 10/5

9:22 a.m.-1:30 p.m.

1 stop3h 08m

C$ 309

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 2/5

2:15 p.m.-5:58 p.m.

1 stop4h 43m

Chicago Midway

Mon 4/5

6:38 p.m.-10:56 p.m.

1 stop3h 18m

C$ 309

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 22/4

12:55 p.m.-8:40 p.m.

1 stop8h 45m

Chicago O'Hare Intl

Thu 30/4

7:10 a.m.-5:40 p.m.

1 stop9h 30m

C$ 321

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 18/4

2:29 p.m.-7:23 p.m.

1 stop5h 54m

Chicago O'Hare Intl

Tue 21/4

7:14 a.m.-1:39 p.m.

1 stop5h 25m

C$ 321

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/3

Showing 1-10 of 60 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 114). Flying from Canada to Chicago in July is currently the most expensive (average of C$ 200). 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 March 2026.

It’s typically best to fly out from Canada to Chicago in the afternoon. Doing so could potentially save you 32% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Canada to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Canada to Chicago. Price data was last updated on 14 March 2026.

Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Friday mornings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 March 2026.

The most flights from CA0 to CHI are scheduled on a Wednesday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (46 on average).

How often are flights from Canada to Chicago delayed?

About 13% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 8% of flights being delayed.

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 March 2026.
Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet 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
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
425 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,454 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,297 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,483 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,818 reviews
Porter Airlines
8.0
Very good
425 reviews
Check prices

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 50m. Porter Airlines provides one of the quickest options available for as low as C$ 275. 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$ 116. Porter Airlines flights start at C$ 123 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: Emirates (100%), Copa Airlines (85%), Republic Airways( 75%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 199. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 259 on average, our data indicates C$ 1,556 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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 114). Flying from Canada to Chicago in July is currently the most expensive (average of C$ 200). 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
Pearson Intl to Midway flights
Toronto Island to Midway flights
Calgary to O'Hare Intl flights
Toronto Island to O'Hare Intl flights
Pierre Elliott Trudeau Intl to Midway flights
Winnipeg to O'Hare Intl flights
Vancouver Intl to Midway flights
Ottawa to O'Hare Intl flights
Pearson Intl to St. Louis flights
Edmonton to O'Hare Intl flights
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Calgary to Midway flights
Ottawa to Midway flights
Québec City to O'Hare Intl flights
Edmonton to Midway flights
Halifax to Midway flights
Vancouver Intl to St. Louis flights
Hamilton to O'Hare Intl flights
Victoria to O'Hare Intl flights
Québec City to Midway flights
Pierre Elliott Trudeau Intl to St. Louis flights
Buffalo to O'Hare Intl flights
Mexico City to O'Hare Intl flights
Victoria to Midway flights
Saskatoon to O'Hare Intl flights
Detroit to O'Hare Intl flights
Edmonton to St. Louis flights
Region of Waterloo Intl to O'Hare Intl flights
Regina to O'Hare Intl flights
Grande Prairie to O'Hare Intl flights
Saskatoon to Midway flights
Grande Prairie to Midway flights
Seattle to O'Hare Intl flights
Québec City to St. Louis flights
Halifax to St. Louis flights
Fort McMurray to O'Hare Intl flights
Calgary to St. Louis flights
Pearson Intl to Peoria flights
Kelowna to Midway flights
Sudbury to O'Hare Intl flights
Kelowna to O'Hare Intl flights

Top 7 airlines flying from Canada to Chicago

Discover the top 7 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 20 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 113AverageC$ 387FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 121AverageC$ 501FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 147AverageC$ 379FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 167AverageC$ 463FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 170AverageC$ 387FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 176AverageC$ 372FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Alaska AirlinesCheapestC$ 384AverageC$ 496FlexibilityNo cancel feeOn-time75%
Search Alaska 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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