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$54+ Cheap flights from Illinois to Canada

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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YYZ
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Illinois to Canada

Cheapest flights from Illinois to Canada
Explore the most affordable flight options available from Illinois to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Trip.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/129:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$383
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:30 amORD - YYZ
1 stop14h 50mMultiple Airlines
Mon 1/123:40 pmYYZ - ORD
1 stop20h 42mMultiple Airlines
Deal found 12/22$385
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:35 amORD - YYZ
1 stop15h 45mMultiple Airlines
Mon 1/123:40 pmYYZ - ORD
1 stop20h 42mMultiple Airlines
Deal found 12/22$407
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:45 amORD - YYZ
1 stop33h 05mMultiple Airlines
Mon 1/127:00 amYYZ - ORD
1 stop29h 22mMultiple Airlines
Deal found 12/22$425
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:00 amORD - YYZ
1 stop3h 19mMultiple Airlines
Mon 1/123:40 pmYYZ - ORD
1 stop20h 42mMultiple Airlines
Deal found 12/22$436
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:25 amORD - YYZ
2 stops31h 55mMultiple Airlines
Mon 1/127:00 amYYZ - ORD
1 stop29h 22mMultiple Airlines
Deal found 12/22$441
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:20 amORD - YTZ
2 stops13h 43mMultiple Airlines
Mon 1/126:15 pmYTZ - ORD
1 stop5h 27mMultiple Airlines
Deal found 12/22$452
This FlightHub deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/129:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$464
This FlightHub deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 1/22:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/21$466
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:00 amORD - YYZ
1 stop3h 19mWestJet
Mon 1/1210:15 pmYYZ - ORD
2 stops20h 40mWestJet
Deal found 12/22$468
This FlightHub deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 1/99:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/20$471
This Kiwi.com deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/21$479

Find flight deals from Illinois to Canada

Keep the following information in mind while searching for Illinois to Canada flight deals. Data was last updated December 23, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$169
(Mytrip)

One-way from

$54
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$319

Good round-trip deal

$205 or less

Good one-way deal

$95 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
Search Deals
From Illinois to Canada
Search Deals
One-way flight from Illinois to Canada
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Canada.
Search Deals
Price to beat on a one-way flight from Illinois to Canada.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Canada 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 2,558,603 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Illinois to Canada that are best for you.

Fly from

Illinois

Fly to

Canada

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/19

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 2/23

9:15 am-10:05 am

Nonstop1h 50m

$194

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 2/18

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Fri 2/20

6:45 am-10:05 am

1 stop4h 20m

$203

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/19

11:05 am-5:45 pm

1 stop5h 40m

Montreal Pierre Elliott Trudeau Intl

Wed 2/25

6:45 am-10:10 am

1 stop4h 25m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/23

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Tue 1/27

9:20 am-10:10 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 1/18

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 1/15

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Mon 1/19

9:20 am-10:10 am

Nonstop1h 50m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 1/26

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sat 1/31

11:00 am-11:50 am

Nonstop1h 50m

$206

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 1/28

7:00 am-9:53 pm

1 stop15h 53m

Calgary

Mon 2/2

6:15 am-11:59 pm

1 stop16h 44m

$221

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/5

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 2/8

7:00 am-7:52 pm

2 stops13h 52m

$223

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sun 1/18

2:30 pm-3:20 pm

Nonstop1h 50m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Canada

Have a flexible travel schedule? Discover the best time to fly to Canada from Illinois 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 Illinois to Canada

What is the cheapest month to book a flight from Illinois to Canada?

Currently, March is the cheapest month in which you can book a flight from Illinois to Canada (average of $79). Flying from Illinois to Canada in December is currently the most expensive (average of $161). 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 IL to CA?

Find hourly flight availability from Illinois to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

A simple way to save on the total cost of your ticket is to fly from Illinois to Canada in the evening. If you’re flexible enough to do this you can expect to save up to 35% on your trip compared to booking a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Illinois to Canada. Price data was last updated on December 16, 2024.

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

Weekly flight availability from Illinois to Canada

Explore weekly flight availability from Illinois to Canada. 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 December 23, 2025.

The most flights from USIL to CA0 are scheduled on a Monday (62 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (32 on average).

Related info for your journey

Find useful and relevant information for your journey from Illinois to Canada. 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 Illinois to Canada?

    For as low as $194, Porter Airlines can have you in Canada from Illinois in 1h 42m. The distance between Illinois and Canada is about 442 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Illinois to Canada one-way?

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at $54. WestJet flights start at $57 while deals on Porter Airlines start at $58 one-way.

  • Can I find deals for flights from Illinois to Canada that include hotel bookings?

    Yes. In addition to deals on Illinois to Canada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Canada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Canada.

  • Can I find deals for business class flights from Illinois to Canada?

    Yes. Cheapflights offers flight deals from Illinois to Canada 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 Illinois to Canada?

    Currently, March is the cheapest month in which you can book a flight from Illinois to Canada (average of $79). Flying from Illinois to Canada in December is currently the most expensive (average of $161). 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 Illinois to Canada

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Illinois to Canada

Discover the top 7 airlines that operate flights from Illinois to Canada. 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 2,558,603 searches. Data last updated December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$85Average$406FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$90Average$492FlexibilityNo cancel feeOn-time69%
DeltaCheapest$109Average$418FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$142Average$367FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$185Average$380FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$192Average$458FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$343Average$707FlexibilityNo cancel feeOn-time75%

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