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$75+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTO
oct. 16 — oct. 231
jeu. 10/16
jeu. 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Toronto are usually found in July or September, 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 septembre 16, 2025.

Round-trip from

$199
(Kiwi.com)

One-way from

$75
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$258

Good round-trip deal

$201 or less

Good one-way deal

$90 or less
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. 6% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
jeu. 10/237:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
lun. 10/274:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/15$199
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
mer. 10/227:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
dim. 10/264:00 pmYYZ - ORD
1 stop24h 49mMultiple Airlines
Deal found 9/15$207
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
mar. 10/75:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
lun. 10/134:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/13$212
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/317:51 pmORD - YYZ
1 stop17h 29mMultiple Airlines
ven. 11/712:50 pmYYZ - ORD
1 stop9h 33mMultiple Airlines
Deal found 9/16$214
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
ven. 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
lun. 11/34:00 pmYYZ - ORD
1 stop7h 39mMultiple Airlines
Deal found 9/15$216
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
ven. 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
dim. 11/94:00 pmYYZ - ORD
1 stop19h 42mMultiple Airlines
Deal found 9/15$217
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
lun. 10/67:43 pmORD - YYZ
1 stop17h 22mMultiple Airlines
lun. 10/134:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/13$218
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sam. 11/16:00 amORD - YYZ
1 stop7h 20mMultiple Airlines
lun. 11/34:00 pmYYZ - ORD
1 stop7h 39mMultiple Airlines
Deal found 9/15$220
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
ven. 10/315:25 amORD - YYZ
1 stop13h 35mMultiple Airlines
dim. 11/24:00 pmYYZ - ORD
1 stop24h 49mMultiple Airlines
Deal found 9/15$223
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
jeu. 10/2312:53 pmORD - YYZ
1 stop7h 14mMultiple Airlines
dim. 10/264:00 pmYYZ - ORD
1 stop24h 49mMultiple Airlines
Deal found 9/14$224
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sam. 10/255:05 amORD - YYZ
1 stop8h 00mMultiple Airlines
lun. 10/274:00 pmYYZ - ORD
1 stop8h 44mMultiple Airlines
Deal found 9/14$226
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sam. 10/189:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
dim. 10/197:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/14$240

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 septembre 16, 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

dim. 10/12

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

dim. 10/19

3:35 pm-4:24 pm

Nonstop1h 49m

$241

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jeu. 10/23

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

jeu. 10/30

3:00 pm-11:25 pm

1 stop9h 25m

$246

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

mer. 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

jeu. 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

$250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

mar. 10/7

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

mer. 10/8

7:50 am-8:39 am

Nonstop1h 49m

$255

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

mer. 10/22

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

ven. 10/24

3:35 pm-4:24 pm

Nonstop1h 49m

$255

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

mer. 10/29

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

mer. 11/5

9:15 am-10:05 am

Nonstop1h 50m

$273

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jeu. 10/9

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

dim. 10/12

7:50 am-8:39 am

Nonstop1h 49m

$275

ChicagoHamilton

ORD - YHM

ORDYHM

Chicago O'Hare Intl

ven. 10/10

5:30 pm-12:40 am

1 stop30h 10m

Hamilton

dim. 10/12

6:00 am-4:43 pm

1 stop11h 43m

$276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

sam. 10/11

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

dim. 10/12

7:50 am-8:39 am

Nonstop1h 49m

$276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jeu. 10/9

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

mar. 10/14

3:35 pm-4:24 pm

Nonstop1h 49m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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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

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 September 12, 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, January is the cheapest month in which you can book a flight from Chicago to Toronto (average of $243). Flying from Chicago to Toronto in August is currently the most expensive (average of $348). 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 septembre 16, 2025.

It’s optimal to fly from Chicago to Toronto in the morning. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight in the afternoon.

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 September 14, 2025.

Travelers seeking maximum savings on their Chicago to Toronto flight should consider departing on Thursday evenings when fares are most often at their lowest. Saturday afternoons 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 septembre 16, 2025.

The most flights from CHI to YTO are scheduled on a Monday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).

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 septembre 16, 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
363 reviews

Food

7.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.1

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
363 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.1

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
438 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.1

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
8,924 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.1

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.1

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Food

7.6

Comfort

7.9

Entertainment

7.0

Overall

7.9

Boarding

8.1

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?

    Porter Airlines, WestJet, and Air Canada can get you from Chicago to Toronto in just under 1h 42m. Your travel time can differ by up to 28h 28m. 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 $146 and $187, respectively. You may be able to fly from Chicago to Toronto for 58% 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 $84 on Porter Airlines. Other airlines that offer cheap prices include WestJet from $114 and Air Canada from $138 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 (88%), Envoy Air (86%) or SkyWest Airlines (81%) 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 $762, our data shows the cheapest flight currently is $74. When looking at the most popular route, (Chicago O'Hare Intl - Toronto Pearson Intl), you can expect to pay $199 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, January is the cheapest month in which you can book a flight from Chicago to Toronto (average of $243). Flying from Chicago to Toronto in August is currently the most expensive (average of $348). 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
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Midway to Pearson Intl flights
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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 Hamilton flights
O'Hare Intl to Thunder Bay flights
Midway to Thunder Bay flights
O'Hare Intl to London flights
St. Louis to Ottawa flights
Bloomington to Pierre Elliott Trudeau Intl flights
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Evansville to Pierre Elliott Trudeau Intl flights
Peoria to Pierre Elliott Trudeau Intl flights
Springfield to Pearson Intl flights
Champaign to Pearson Intl flights
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O'Hare Intl to Kingston flights
Bloomington to Ottawa flights
Dubuque 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 septembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$118Average$270FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$146Average$307FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$187Average$257FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$226Average$391FlexibilityNo cancel feeOn-time71%

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