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$77+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTO
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
1 adult, Economy
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Find cheap flights from Chicago to Toronto with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Toronto are usually found in September or July, booked 86 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap 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 October 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$184
(American Airlines)

One-way from

$77
(American Airlines)

Popular in

January

Cheapest in

September

Average price

$280

Good round-trip deal

$222 or less

Good one-way deal

$89 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
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From Chicago (CHI) to Toronto (YTO)
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One-way flight from Chicago (CHI) to Toronto (YTO)
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Highest demand for flights based on searches. 11% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Toronto (YTO).
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Price to beat on a one-way flight from Chicago (CHI) to Toronto (YTO).
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Find 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 October 10, 2025.

This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:39 amORD - YYZ
Nonstop1h 51mAmerican Airlines
Sun 12/71:10 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 10/9$184
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:04 amORD - YYZ
1 stop4h 52mAmerican Airlines
Mon 12/86:24 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 10/9$194
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:03 amORD - YYZ
Nonstop1h 43mAmerican Airlines
Wed 11/1211:59 amYYZ - ORD
1 stop6h 53mAmerican Airlines
Deal found 10/9$200
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Wed 11/123:26 pmORD - YYZ
1 stop22h 14mMultiple Airlines
Sun 11/164:00 pmYYZ - ORD
1 stop19h 42mMultiple Airlines
Deal found 10/9$210
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/303:59 pmORD - YYZ
Nonstop1h 45mAmerican Airlines
Sun 11/24:44 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 10/9$213
This United deal was found by Cheapflights users on 10/7. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:13 pmORD - YYZ
Nonstop1h 49mMultiple Airlines
Fri 1/212:05 pmYYZ - ORD
Nonstop1h 56mMultiple Airlines
Deal found 10/7$215
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:50 amORD - YYZ
1 stop7h 40mAmerican Airlines
Thu 11/134:44 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 10/9$217
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Wed 11/123:26 pmORD - YYZ
1 stop22h 14mMultiple Airlines
Mon 11/177:00 amYYZ - ORD
1 stop27h 47mMultiple Airlines
Deal found 10/9$221
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/510:52 amORD - YYZ
1 stop10h 20mMultiple Airlines
Sun 11/94:00 pmYYZ - ORD
1 stop19h 42mMultiple Airlines
Deal found 10/8$224
This Air Canada deal was found by Cheapflights users on 10/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1310:00 amORD - YYZ
Nonstop1h 40mAir Canada
Sat 1/108:15 amYYZ - ORD
Nonstop1h 58mAir Canada
Deal found 10/7$225
This Delta deal was found by Cheapflights users on 10/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:35 pmMDW - YYZ
1 stop3h 20mDelta
Sun 11/25:15 amYYZ - MDW
1 stop3h 25mDelta
Deal found 10/9$233
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/169:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/8$235

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 October 10, 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

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 12/26

6:16 pm-9:21 pm

Nonstop2h 05m

Toronto Pearson Intl

Thu 1/1

8:55 am-10:00 am

Nonstop2h 05m

$225

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 12/20

9:20 pm-11:59 pm

Nonstop1h 39m

Toronto Pearson Intl

Sat 1/3

9:00 pm-10:05 pm

Nonstop2h 05m

$225

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 10/30

7:10 am-2:45 pm

1 stop6h 35m

Toronto Pearson Intl

Sun 11/2

5:15 am-8:43 am

1 stop4h 28m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 11/1

6:08 am-3:59 pm

1 stop8h 51m

Toronto Pearson Intl

Sun 11/2

5:15 am-8:43 am

1 stop4h 28m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 11/7

1:25 pm-10:55 pm

1 stop8h 30m

Toronto Pearson Intl

Sun 11/9

12:08 pm-6:26 pm

1 stop7h 18m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 11/20

6:45 am-2:48 pm

1 stop7h 03m

Toronto Pearson Intl

Mon 11/24

6:30 am-11:34 am

1 stop6h 04m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 11/9

6:45 am-2:48 pm

1 stop7h 03m

Toronto Pearson Intl

Wed 11/12

2:10 pm-10:35 pm

1 stop9h 25m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 11/6

8:55 am-2:45 pm

1 stop4h 50m

Toronto Pearson Intl

Sun 11/9

12:08 pm-6:26 pm

1 stop7h 18m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 11/8

2:35 pm-8:42 pm

1 stop5h 07m

Toronto Pearson Intl

Tue 11/11

5:08 pm-10:35 pm

1 stop6h 27m

$233

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 11/20

6:45 am-2:48 pm

1 stop7h 03m

Toronto Pearson Intl

Sun 11/23

6:30 am-11:34 am

1 stop6h 04m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Toronto flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 October 3, 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 86 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, October is the cheapest month in which you can book a flight from Chicago to Toronto (average of $105). Flying from Chicago to Toronto in July is currently the most expensive (average of $173). 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 October 10, 2025.

It’s optimal to fly from Chicago to Toronto in the morning. By choosing this option you can save up to 26% 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 October 5, 2025.

Travelers seeking maximum savings on their Chicago to Toronto flight should consider departing on Wednesday afternoons 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 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 October 10, 2025.

The most flights from CHI to YTO are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (54 on average).

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

The best insider tips for Chicago to Toronto flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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 October 10, 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
7.9
Good
377 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
377 reviews
Porter Airlines
7.9
Good
377 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Transat
7.7
Good
454 reviews
Porter Airlines
7.9
Good
377 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,966 reviews
Porter Airlines
7.9
Good
377 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,043 reviews
Porter Airlines
7.9
Good
377 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,263 reviews
Porter Airlines
7.9
Good
377 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Overall

7.9

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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?

    United Airlines, Delta, and Porter Airlines can get you from Chicago to Toronto in just under 1h 42m. Your travel time can differ by up to 4h 53m. 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 $118. Additional round-trip tickets that might be worth considering are offered by United Airlines and Porter Airlines, with the lowest prices starting at $145 and $185, respectively. You may be able to fly from Chicago to Toronto for 57% 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 $77 on American Airlines. Other airlines that offer cheap prices include Delta from $89 and Porter Airlines from $106 one-way.

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

    While some choose either Chicago Midway - Toronto Island or Chicago Midway - Toronto Pearson Intl, 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 Qatar Airways (93%), Finnair (88%) or Envoy Air (87%) 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 $748, our data shows the cheapest flight currently is $84. When looking at the most popular route, (Chicago O'Hare Intl - Toronto Pearson Intl), you can expect to pay $135 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, October is the cheapest month in which you can book a flight from Chicago to Toronto (average of $105). Flying from Chicago to Toronto in July is currently the most expensive (average of $173). 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 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
O'Hare Intl to Toronto Island flights
Midway to Pearson Intl flights
Midway to Toronto Island 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
O'Hare Intl to London flights
O'Hare Intl to Hamilton flights
St. Louis to Ottawa flights
Moline to Pearson Intl flights
Midway to Thunder Bay flights
O'Hare Intl to Thunder Bay flights
Evansville to Pearson Intl flights
Peoria to Pierre Elliott Trudeau Intl flights
Springfield to Pearson Intl flights
Bloomington to Pierre Elliott Trudeau Intl flights
O'Hare Intl to Kingston flights
Bloomington to Ottawa flights
Evansville to Pierre Elliott Trudeau Intl flights
Dubuque to Pearson Intl flights
Champaign 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 October 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$118Average$268FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$145Average$310FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$185Average$240FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$230Average$389FlexibilityNo cancel feeOn-time71%

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