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$83+ Cheap flights from Chicago (CHI) to Toronto (YTO)

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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTO
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Find cheap flights from Chicago to Toronto with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago to Toronto are usually found in September or July, booked 75 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Chicago to Toronto

Cheapest flights from Chicago to Toronto
Explore the most affordable flight options available from Chicago to Toronto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:50 amORD - YYZ
1 stop13h 56mUnited Airlines
Wed 12/319:00 pmYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 12/9$253
This United Airlines deal was found by Cheapflights users on 12/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:50 amORD - YYZ
1 stop13h 56mUnited Airlines
Mon 1/56:40 pmYYZ - ORD
1 stop5h 55mUnited Airlines
Deal found 12/9$268
This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:21 pmORD - YYZ
1 stop4h 25mUnited Airlines
Mon 12/299:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 12/11$273
This United Airlines deal was found by Cheapflights users on 12/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:21 pmORD - YYZ
1 stop4h 25mUnited Airlines
Sun 12/289:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
Deal found 12/10$274
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 1/29:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/10$306
This Kiwi.com deal was found by Cheapflights users on 12/9. 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
Sun 1/49:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/9$327
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/246:40 amORD - YTZ
2 stops33h 08mMultiple Airlines
Wed 12/316:45 amYTZ - ORD
1 stop16h 22mMultiple Airlines
Deal found 12/10$359
This United Airlines deal was found by Cheapflights users on 12/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/251:13 pmORD - YYZ
Nonstop1h 49mUnited Airlines
Thu 12/257:40 pmYYZ - ORD
1 stop5h 04mUnited Airlines
Deal found 12/8$362
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/256:02 pmORD - YYZ
1 stop13h 56mWestJet
Tue 1/67:50 amYYZ - ORD
1 stop9h 32mWestJet
Deal found 12/9$363
This Trip.com deal was found by Cheapflights users on 12/9. 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.
Thu 12/254:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 1/29:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/9$367
This United Airlines deal was found by Cheapflights users on 12/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:21 pmORD - YYZ
1 stop4h 25mUnited Airlines
Thu 1/15:30 pmYYZ - ORD
Nonstop2h 20mUnited Airlines
Deal found 12/9$368
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/307:44 amMDW - YTZ
1 stop23h 36mMultiple Airlines
Fri 1/29:20 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 12/10$369

Find flight deals from Chicago to Toronto

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Toronto (YTO). 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 December 12, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$184
(Booking.com)

One-way from

$83
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$294

Good round-trip deal

$241 or less

Good one-way deal

$122 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 Chicago (CHI) to Toronto (YTO)
Search Deals
One-way flight from Chicago (CHI) to Toronto (YTO)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 Chicago (CHI) to Toronto (YTO).
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Toronto (YTO).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Toronto 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 12, 2025.
Use the filters below to find and compare flights from Chicago to Toronto that are best for you.

Fly from

Chicago

Fly to

Toronto

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/26

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

Sat 2/28

11:05 am-11:55 am

Nonstop1h 50m

$186

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/5

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 2/8

9:15 am-10:05 am

Nonstop1h 50m

$194

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 1/25

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 2/1

9:15 am-10:05 am

Nonstop1h 50m

$196

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 1/30

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sat 1/31

11:00 am-11:50 am

Nonstop1h 50m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 1/24

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Thu 1/29

9:20 am-10:10 am

Nonstop1h 50m

$198

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 1/26

6:28 pm-9:21 pm

Nonstop1h 53m

Toronto Pearson Intl

Mon 2/2

3:30 pm-4:40 pm

Nonstop2h 10m

$211

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 1/30

9:15 pm-11:59 pm

Nonstop1h 44m

Toronto Pearson Intl

Mon 2/2

9:00 pm-10:05 pm

Nonstop2h 05m

$211

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sat 1/24

3:35 pm-9:35 pm

1 stop5h 00m

Toronto Island

Sat 1/31

3:30 pm-8:10 pm

1 stop5h 40m

$213

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 2/13

7:00 am-5:18 pm

1 stop9h 18m

Toronto Pearson Intl

Sun 2/15

5:15 pm-8:44 pm

1 stop4h 29m

$233

ChicagoToronto

MDW - YYZ

MDWYYZ

Chicago Midway

Tue 2/10

1:26 pm-7:08 pm

1 stop4h 42m

Toronto Pearson Intl

Fri 2/13

10:05 am-5:37 pm

1 stop8h 32m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 60 results
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Compare providers for flights from Chicago to Toronto

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Toronto in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Toronto flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Chicago-Toronto flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Chicago-Toronto flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Toronto flights, Cheapflights users trust Mytrip the most. Mytrip has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Toronto flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Toronto

Have a flexible travel schedule? Discover the best time to fly to Toronto from Chicago 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 Chicago to Toronto

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Toronto. Price data was last updated on December 5, 2025.

The price you pay for your flight from Chicago to Toronto may vary depending on when you book. For the best chance of a lower fare, look to book 75 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Toronto?

Currently, March is the cheapest month in which you can book a flight from Chicago to Toronto (average of $79). Flying from Chicago to Toronto in December is currently the most expensive (average of $210). 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 CHI to YTO?

Find hourly flight availability from Chicago to Toronto. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s optimal to fly from Chicago to Toronto in the morning. By choosing this option you can save up to 48% on the cost of your flight, compared to a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Toronto. Price data was last updated on December 6, 2025.

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

Weekly flight availability from Chicago to Toronto

Explore weekly flight availability from Chicago to Toronto. 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 12, 2025.

The most flights from CHI to YTO are scheduled on a Monday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 on average).

How much does it cost to fly round-trip from Chicago to Toronto?

How often are flights from Chicago to Toronto delayed?

About 17% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 130 minutes.

What is the most punctual flight time for Chicago to Toronto 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?

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

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

Over the last year, Korean Air have had the lowest number of delays on this route, with just 11% of flights being delayed.

The best insider tips for Chicago to Toronto flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Toronto trip
Airlines
United Airlines

United's Economy Plus offers extra legroom seats, enhancing comfort for short flights.


United Polaris offers lie-flat seats and upscale amenities, perfect for premium travel.

Read more about United AirlinesBy Harriet Baskas
Air Canada

Economy Latitude offers priority check-in and two checked bags, ideal for efficient travel.


Air Canada provides high-speed Wi-Fi on most flights, book in advance for best rates.

Read more about Air CanadaBy Jessica Macdonald
Airports
ORD

For a quick departure, use the 'L' train from downtown Chicago to ORD, avoiding traffic delays common with taxis or rideshares.

Read more about ORDBy Ramsey Qubein
YYZ

For a budget-friendly arrival, use public transportation from YYZ to downtown Toronto, despite needing a connection.

Read more about YYZBy Kaitlyn McInnis
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Jessica Macdonald

Jessica Macdonald

Expert on Air Canada

Jessica Macdonald

Jessica Macdonald

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYZ

Kaitlyn McInnis

Kaitlyn McInnis

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more

Reviews of airlines servicing Toronto

Get insights into the airlines that provide service to Toronto. 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 Toronto. Reviews last updated December 12, 2025.
Read reviews from past customers who have flown Porter Airlines, Air Transat, and United Airlines from Chicago to Toronto. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
398 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
398 reviews
Porter Airlines
8.0
Very good
398 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Transat
7.8
Good
480 reviews
Porter Airlines
8.0
Very good
398 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,095 reviews
Porter Airlines
8.0
Very good
398 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,050 reviews
Porter Airlines
8.0
Very good
398 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,516 reviews
Porter Airlines
8.0
Very good
398 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

7.0

Food

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

Related info for your journey

Find useful and relevant information for your journey from Chicago to Toronto. 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 Chicago to Toronto?

    Porter Airlines, United Airlines, and Air Canada can get you from Chicago to Toronto in just under 1h 42m. Your travel time can differ by up to 3h 18m. There are 442 mi between Chicago and Toronto. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago to Toronto round-trip?

    Flying on Air Canada is currently your cheapest option to Toronto, with prices starting at $101. Additional round-trip tickets that might be worth considering are offered by Porter Airlines and United Airlines, with the lowest prices starting at $109 and $139, respectively. You may be able to fly from Chicago to Toronto for 62% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago to Toronto one-way?

    One-way options have recently been found by users for as low as $64 on Air Canada. Other airlines that offer cheap prices include United Airlines from $69 and American Airlines from $74 one-way.

  • What are the most popular routes from Chicago to Toronto?

    While some choose either Chicago Midway - Toronto Island or Chicago O'Hare Intl - Toronto Island, Chicago O'Hare Intl - Toronto Pearson Intl is the most popular route from Chicago to Toronto.

  • What are the most reliable airlines from Chicago to Toronto?

    No one likes to see their flight delayed. When booking a flight from Chicago to Toronto consider choosing Korean Air (94%), SkyWest Airlines (82%) or Japan Airlines (79%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Toronto?

    While on average a flight from Chicago to Toronto is generally $922, our data shows the cheapest flight currently is $94. When looking at the most popular route, (Chicago O'Hare Intl - Toronto Pearson Intl), you can expect to pay $166 for that flight.

  • Can I find deals for flights from Chicago to Toronto that include hotel bookings?

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

  • How can I find direct flights from Chicago to Toronto?

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

  • Can I find deals for business class flights from Chicago to Toronto?

    Yes. Cheapflights offers flight deals from Chicago to Toronto 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 Chicago to Toronto?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Toronto (average of $79). Flying from Chicago to Toronto in December is currently the most expensive (average of $210). 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

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Alternative routes for Chicago to Toronto

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Pearson Intl flights
O'Hare Intl to Pierre Elliott Trudeau Intl flights
Midway to Toronto Island flights
O'Hare Intl to Toronto Island flights
Midway to Pearson Intl flights
Midway to Pierre Elliott Trudeau Intl flights
St. Louis to Pearson Intl flights
O'Hare Intl to Ottawa flights
St. Louis to Pierre Elliott Trudeau Intl flights
Midway to Ottawa flights
St. Louis to Ottawa flights
O'Hare Intl to London flights
O'Hare Intl to Hamilton flights
Moline to Pearson Intl flights
O'Hare Intl to Thunder Bay flights
Evansville to Pierre Elliott Trudeau Intl flights
Midway to Thunder Bay flights
Evansville to Pearson Intl flights
Peoria to Pierre Elliott Trudeau Intl flights
Dubuque to Pearson Intl flights
Champaign to Pearson Intl flights
Bloomington to Pierre Elliott Trudeau Intl flights
Bloomington to Ottawa flights
O'Hare Intl to Kingston flights
Springfield to Pearson Intl flights

Top 4 airlines flying from Chicago to Toronto

Discover the top 4 airlines that operate flights from Chicago to Toronto. 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$116Average$246FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$146Average$300FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$185Average$350FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$215Average$378FlexibilityNo cancel feeOn-time71%

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