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$136+ Cheap flights from Toronto (YTO) to Chicago (CHI)

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Aug 29 — Sep 51
Sat 8/29
Sat 9/5
1 adult, Economy
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Find cheap flights from Toronto to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Toronto to Chicago are usually found in September or February, booked 88 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Toronto to Chicago

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2026.

This Trip.com deal was found by Cheapflights users on 7/26. 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.
Wed 9/94:00 pm
YYZ
-
ORD
1 stop5h 12m
Air Canada
Wed 9/163:45 pm
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 7/26$205
This Trip.com deal was found by Cheapflights users on 7/29. 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 8/318:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 9/23:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/29$205
This Trip.com deal was found by Cheapflights users on 7/27. 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 9/106:50 pm
YYZ
-
ORD
Nonstop1h 58m
Air Canada
Sun 9/135:35 pm
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 7/27$206
This Trip.com deal was found by Cheapflights users on 7/29. 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 8/278:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 9/211:45 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/29$206
This Justfly.com deal was found by Cheapflights users on 7/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 9/13:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 7/29$207
This Trip.com deal was found by Cheapflights users on 7/25. 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.
Fri 9/189:30 am
YTZ
-
ORD
1 stop6h 22m
Air Canada
Mon 9/218:45 am
ORD
-
YTZ
1 stop6h 05m
Air Canada
Deal found 7/25$207
This Trip.com deal was found by Cheapflights users on 7/25. 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.
Fri 9/1812:25 pm
YYZ
-
ORD
Nonstop1h 58m
Air Canada
Mon 9/218:40 pm
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 7/25$208
This Trip.com deal was found by Cheapflights users on 7/29. 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.
Fri 9/47:45 pm
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Sun 9/67:25 am
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 7/29$208
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 9/411:00 am
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Wed 9/912:59 pm
ORD
-
YYZ
Nonstop1h 47m
United Airlines
Deal found 7/28$209
This Air Canada deal was found by Cheapflights users on 7/28. 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.
Wed 9/29:30 am
YTZ
-
ORD
1 stop6h 25m
Air Canada
Sat 9/127:25 am
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 7/28$209
This Air Canada deal was found by Cheapflights users on 7/28. 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.
Wed 9/26:55 pm
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Wed 9/99:55 am
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 7/28$210
This Air Canada deal was found by Cheapflights users on 7/29. 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.
Fri 9/47:45 pm
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Sun 9/137:25 am
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 7/29$210

Find flight deals from Toronto to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Chicago (CHI). 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 July 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$205
(Trip.com)

One-way from

$136
(Air Canada)

Popular in

May

Cheapest in

September

Average price

$283

Good round-trip deal

$205 or less

Good one-way deal

$136 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
Search Deals
From Toronto (YTO) to Chicago (CHI)
Search Deals
One-way flight from Toronto (YTO) to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2026.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/24

11:00 am-12:00 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sun 9/27

9:18 pm-11:59 pm

Nonstop1h 41m

$209

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 9/3

10:20 am-8:05 pm

2 stops10h 45m

Chicago O'Hare Intl

Sun 9/6

7:25 am-10:07 am

Nonstop1h 42m

$217

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 9/1

11:00 am-12:00 pm

Nonstop2h 00m

Chicago O'Hare Intl

Wed 9/30

3:40 pm-11:18 pm

1 stop6h 38m

$218

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 9/18

7:00 am-8:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Wed 9/23

7:09 am-9:54 am

Nonstop1h 45m

$222
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 9/9

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Sun 9/13

3:20 pm-6:00 pm

Nonstop1h 40m

$228

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 9/8

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Sun 9/13

3:20 pm-6:00 pm

Nonstop1h 40m

$228

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 8/26

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Fri 8/28

10:25 am-1:05 pm

Nonstop1h 40m

$231

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/27

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Thu 9/3

3:20 pm-6:00 pm

Nonstop1h 40m

$234

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/2

10:15 am-11:21 am

Nonstop2h 06m

Chicago O'Hare Intl

Sun 9/27

8:50 am-2:19 pm

1 stop4h 29m

$237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/9

12:08 pm-4:13 pm

1 stop5h 05m

Chicago O'Hare Intl

Wed 9/16

5:10 pm-10:59 pm

1 stop4h 49m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Toronto to Chicago

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 Toronto to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust 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 Toronto-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto-Chicago 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 Toronto-Chicago 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 Toronto to Chicago

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

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

Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of $252). Flying from Toronto to Chicago in December is currently the most expensive (average of $308). 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 YTO to CHI?

Find hourly flight availability from Toronto to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2026.

A simple way to save on the total cost of your ticket is to fly from Toronto to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the afternoon.

Weekly flight availability from Toronto to Chicago

Explore weekly flight availability from Toronto to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 30, 2026.

The most flights from YTO to CHI are scheduled on a Monday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 on average).

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

Airfare is below average for this route at the moment.
Toronto to Chicago flights typically cost between $215 and $341 in September.
The cheapest round-trip price found within the last 5 days was $205 on Air Canada (Sep 9-Sep 16).

How often are flights from Toronto to Chicago delayed?

About 14% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 136 minutes.

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

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

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

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

Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

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

To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 87 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on July 25, 2026.

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

The best insider tips for Toronto to Chicago 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 Toronto to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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 Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 30, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,United Airlines, andAmerican Airlines from Toronto to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
449 reviews

Entertainment

6.9

Food

7.5

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
449 reviews
Porter Airlines
8.0
Very good
449 reviews

Entertainment

6.9

Food

7.5

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
United Airlines
7.4
Good
10,046 reviews
Porter Airlines
8.0
Very good
449 reviews

Entertainment

6.9

Food

7.5

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
American Airlines
7.1
Good
11,842 reviews
Porter Airlines
8.0
Very good
449 reviews

Entertainment

6.9

Food

7.5

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,406 reviews
Porter Airlines
8.0
Very good
449 reviews

Entertainment

6.9

Food

7.5

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

Related info for your journey

Find useful and relevant information for your journey from Toronto to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Toronto to Chicago?

    United Airlines, Air Canada, and Porter Airlines can get you from Toronto to Chicago in just under 1h 50m. Your travel time can differ by up to 8h 55m. There are 442 mi between Toronto and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Our cheapest airline available from Toronto to Chicago is Air Canada. Our recent data shows that you can find tickets from as low as $137 on this airline. Additional options worth looking into are Porter Airlines and American Airlines, starting at $168 and $189 round-trip. Air Canada is currently priced 49% below the average price you’ll pay for this route.

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

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $111. Users have also found prices from $124 and $125 on United Airlines and Porter Airlines, respectively.

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

    The most popular flight routes from Toronto to Chicago are Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago O'Hare Intl and Toronto Island - Chicago Midway.

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

    Consider Egyptair (95%), Copa Airlines (93%) or Japan Airlines (87%) when booking your flight. These represent the most reliable airlines when flying from Toronto to Chicago.

  • What are the cheapest flights from Toronto to Chicago?

    Looking for the cheapest flight from Toronto to Chicago? While on average our users pay $1,216, our data indicates the cheapest price to be $146. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $209.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of $252). Flying from Toronto to Chicago in December is currently the most expensive (average of $308). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 4 airlines flying from Toronto to Chicago

Discover the top 4 airlines that operate flights from Toronto to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$137Average$291FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$168Average$370FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$189Average$294FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$189Average$284FlexibilityNo cancel feeOn-time69%

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