HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$131+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Toronto to Chicago 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Toronto to Chicago are usually found in April or March, booked 77 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$204
(123 Milhas)

One-way from

$131
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$285

Good round-trip deal

$228 or less

Good one-way deal

$119 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 ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
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

Find 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 February 20, 2025.

This 123 Milhas deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 123 Milhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:00 pmYYZ - ORD
1 stop5h 12mAir Canada
Sat 6/710:40 amORD - YYZ
1 stop6h 18mAir Canada
Deal found 2/20$204
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/203:50 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 3/245:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/19$204
This 123 Milhas deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 123 Milhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2410:25 amYTZ - ORD
1 stop5h 30mAir Canada
Sat 6/710:40 amORD - YTZ
1 stop6h 10mAir Canada
Deal found 2/20$204
This Trip.com deal was found by Cheapflights users on 2/18. 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 3/203:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
Thu 3/275:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 2/18$223
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sat 3/227:55 pmYYZ - ORD
1 stop13h 40mMultiple Airlines
Tue 3/256:25 pmORD - YYZ
2 stops28h 30mMultiple Airlines
Deal found 2/19$224
This Kissandfly.com deal was found by Cheapflights users on 2/19. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/205:30 pmYYZ - ORD
Nonstop2h 09mLufthansa
Mon 3/249:12 pmORD - YYZ
Nonstop1h 47mLufthansa
Deal found 2/19$236
This Kiwi.com deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/189:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 4/1912:55 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 2/20$244
This CheapTicketsDeal deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/126:30 amYYZ - MDW
1 stop13h 03mWestJet
Sun 4/2010:20 amMDW - YYZ
1 stop24h 14mWestJet
Deal found 2/20$244
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2612:45 pmYYZ - ORD
1 stop4h 59mUnited Airlines
Wed 4/3011:15 amORD - YYZ
1 stop4h 54mUnited Airlines
Deal found 2/20$246
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1812:15 pmYYZ - MDW
1 stop7h 05mDelta
Tue 4/223:02 pmMDW - YYZ
1 stop6h 53mDelta
Deal found 2/20$246
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/189:45 amYYZ - ORD
1 stop7h 23mDelta
Sat 4/195:00 pmORD - YYZ
1 stop4h 55mDelta
Deal found 2/20$253
This American Airlines deal was found by Cheapflights users on 2/19. 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 5/31:15 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
Sat 5/109:45 amORD - YYZ
1 stop6h 35mAmerican Airlines
Deal found 2/19$258

Find flights from Toronto to Chicago within your budget

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 February 20, 2025.

Fly from

Toronto

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 5/24

4:00 pm-8:12 pm

1 stop5h 12m

Chicago O'Hare Intl

Sat 6/7

10:40 am-5:58 pm

1 stop6h 18m

$204

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 3/20

3:50 pm-4:40 pm

Nonstop1h 50m

Chicago Midway

Mon 3/24

5:35 pm-8:17 pm

Nonstop1h 42m

$204

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 5/24

10:25 am-2:55 pm

1 stop5h 30m

Chicago O'Hare Intl

Sat 6/7

10:40 am-5:50 pm

1 stop6h 10m

$204

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 3/22

7:55 pm-8:35 am

1 stop13h 40m

Chicago O'Hare Intl

Tue 3/25

6:25 pm-11:55 pm

2 stops28h 30m

$224

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 3/17

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Thu 3/20

5:35 pm-8:17 pm

Nonstop1h 42m

$229

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/12

6:30 am-6:33 pm

1 stop13h 03m

Chicago Midway

Mon 4/21

1:16 pm-11:34 am

1 stop21h 18m

$244

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 4/18

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sat 4/19

12:55 pm-3:37 pm

Nonstop1h 42m

$244

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 4/26

12:45 pm-4:44 pm

1 stop4h 59m

Chicago O'Hare Intl

Wed 4/30

11:15 am-5:09 pm

1 stop4h 54m

$246

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 3/20

10:20 am-12:36 pm

1 stop3h 16m

Chicago Midway

Mon 3/24

2:55 pm-10:38 pm

1 stop6h 43m

$247

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 4/18

9:45 am-4:08 pm

1 stop7h 23m

Chicago O'Hare Intl

Sat 4/19

5:00 pm-10:55 pm

1 stop4h 55m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 34 results
1
2
3
4

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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*3 stars
oojoPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice 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 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.

Travel insights for flights from Toronto to Chicago

Get recent, data-driven insights about flights from Toronto to Chicago including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on February 14, 2025.

To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 77 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 month to book a flight from Toronto to Chicago?

Currently, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of $245). Flying from Toronto to Chicago in March is currently the most expensive (average of $321). 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 February 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Toronto to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 59% on your trip compared to booking a flight at noon.

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 December 16, 2024.

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

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 February 20, 2025.

The most flights from YTO to CHI are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 February 20, 2025.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Delta, Porter Airlines and KLM. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,333 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
380 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,765 reviews
Delta
8.0
Very good
8,219 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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 $204 on this airline. Additional options worth looking into are Porter Airlines and Air Transat, starting at $207 and $229 round-trip. Air Canada is currently priced 26% 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 Porter Airlines. According to our data, you can fly for as low as $131. Users have also found prices from $132 and $136 on Air Canada and United 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 Midway and Toronto Pearson Intl - Chicago Midway.

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

    Consider Emirates (90%), Republic Airways (89%) or ANA (84%) 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 $858, our data indicates the cheapest price to be $129. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $221.

  • 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, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of $245). Flying from Toronto to Chicago in March is currently the most expensive (average of $321). 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 Toronto?

Book flights to Toronto if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$194Average$245FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$210Average$296FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$233Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$323FlexibilityNo cancel feeOn-time71%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.