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Cheap flights from Canada to Chicago from C$ 174

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 20/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
22 Jun — 29 Jun1
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 23 May 2026.

Wed 24/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 26/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/5C$ 275
Wed 24/68:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 24/73:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/5C$ 276
Wed 23/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sat 26/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/5C$ 276
Wed 10/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 12/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/5C$ 277
Thu 11/61:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 14/63:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/5C$ 279
Fri 12/67:20 p.m.
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Sun 14/67:25 a.m.
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 20/5C$ 279
Thu 11/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 15/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/5C$ 280
Fri 18/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Mon 21/97:00 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/5C$ 280
Fri 12/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 15/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/5C$ 282
Thu 3/98:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Tue 8/97:00 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/5C$ 282
Mon 8/68:45 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 10/610:15 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 22/5C$ 283
Tue 1/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sat 5/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/5C$ 283

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 23 May 2026.

Round-trip from

C$ 275

One-way from

C$ 174

Popular in

May

Cheapest in

July

Average price

C$ 395

Good round-trip deal

C$ 290 or less

Good one-way deal

C$ 155 or less
Porter Airlines
  • Porter Airlines
  • 24/6-26/6
  • Nonstop
  • 3h 30m total
  • Canada to Chicago
Search Deals
Air Canada
  • Air Canada
  • 20/6
  • Nonstop
  • 1h 57m total
  • Canada to Chicago
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 25 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 May 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 23 May 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

Thu 25/6

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

Nonstop1h 50m

Chicago Midway

Sun 28/6

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

Nonstop1h 40m

C$ 291

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 21/6

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

Nonstop1h 50m

Chicago Midway

Thu 25/6

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

Nonstop1h 40m

C$ 301

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 20/6

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

Nonstop1h 50m

Chicago Midway

Sat 27/6

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

Nonstop1h 40m

C$ 313

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/6

5:15 p.m.-6:19 p.m.

Nonstop2h 04m

Chicago O'Hare Intl

Sun 14/6

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 320

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 22/7

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

Nonstop1h 50m

Chicago Midway

Tue 28/7

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 328

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 16/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Thu 18/6

9:17 a.m.-5:24 p.m.

1 stop7h 07m

C$ 330

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 18/6

6:05 a.m.-9:14 a.m.

1 stop4h 09m

Chicago Midway

Mon 22/6

1:26 p.m.-11:02 p.m.

1 stop8h 36m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 19/7

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

Nonstop1h 50m

Chicago Midway

Wed 22/7

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 333

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 26/8

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

Nonstop1h 50m

Chicago Midway

Sat 29/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 335

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 10/6

1:00 p.m.-2:06 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sat 13/6

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 338

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/5

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, April is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 352). Flying from Canada to Chicago in July is currently the most expensive (average of C$ 486). 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 23 May 2026.

It’s typically best to fly out from Canada to Chicago in the evening. Doing so could potentially save you 30% on the flight price compared to flying at noon, which is usually more expensive.

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 23 May 2026.

The most flights from CA0 to CHI are scheduled on a Friday (68 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (59 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 135 minutes.

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

Historically, flights departing in the morning 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 Sunday 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.

How far ahead should I book a flight from Canada to Chicago?

The price you pay for your flight from Canada to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 83 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 16 May 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.

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 23 May 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
439 reviews
Check prices

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
439 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
9,751 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
3,345 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
11,642 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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
11,077 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Entertainment

7.0

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

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$ 291. 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 Porter Airlines, which is currently one of the cheapest options available, starting at C$ 123. WestJet flights start at C$ 136 while deals on Air Canada start at C$ 145 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: EVA Air (100%), Copa Airlines (96%), Republic Airways( 84%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 198. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 284 on average, our data indicates C$ 1,379 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, April is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 352). Flying from Canada to Chicago in July is currently the most expensive (average of C$ 486). 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.

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 23 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 113AverageC$ 452FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 121AverageC$ 548FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 148AverageC$ 385FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 168AverageC$ 487FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 177AverageC$ 405FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 184AverageC$ 396FlexibilityNo cancel feeOn-time60%
Search WestJet 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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