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$119+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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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 March or April, booked 81 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$176
(Cheapflightsfares)

One-way from

$119
(Flightnetwork)

Popular in

December

Cheapest in

March

Average price

$261

Good round-trip deal

$192 or less

Good one-way deal

$115 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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From Toronto (YTO) to Chicago (CHI)
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One-way flight from Toronto (YTO) to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
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Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).
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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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 5/285:50 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/29$176
This flugladen.de deal was found by Cheapflights users on 4/29. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/137:55 amYTZ - MDW
Nonstop1h 50mAir Transat
Fri 6/205:50 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 4/29$179
This Ticket deal was found by Cheapflights users on 4/30. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:15 amYYZ - ORD
1 stop4h 37mAir Canada
Sun 6/89:14 pmORD - YYZ
Nonstop1h 44mAir Canada
Deal found 4/30$187
This Trip.com deal was found by Cheapflights users on 4/29. 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.
Sun 6/14:05 pmYTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 6/25:50 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 4/29$190
This Air Canada deal was found by Cheapflights users on 4/30. 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.
Thu 6/197:25 amYTZ - ORD
1 stop4h 59mAir Canada
Mon 6/232:16 pmORD - YTZ
1 stop5h 20mAir Canada
Deal found 4/30$198
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/53:14 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 6/85:00 amORD - YYZ
1 stop4h 21mAmerican Airlines
Deal found 4/30$228
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Thu 5/292:10 pmYYZ - ORD
Nonstop1h 55mMultiple Airlines
Mon 6/29:08 pmORD - YYZ
1 stop14h 22mMultiple Airlines
Deal found 4/30$247
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 6/56:30 amYYZ - MDW
1 stop6h 58mDelta
Wed 6/119:24 amMDW - YYZ
1 stop6h 51mDelta
Deal found 4/30$260
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 6/56:30 amYYZ - ORD
1 stop7h 11mDelta
Fri 6/61:45 pmORD - YYZ
1 stop8h 13mDelta
Deal found 4/30$264
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/297:00 amYYZ - ORD
Nonstop1h 59mUnited Airlines
Thu 6/510:00 amORD - YYZ
Nonstop1h 42mUnited Airlines
Deal found 4/30$290
This Trip.com deal was found by Cheapflights users on 4/29. 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.
Wed 5/2112:30 pmYYZ - MDW
1 stop6h 15mWestJet
Fri 5/3012:48 pmMDW - YYZ
1 stop8h 08mWestJet
Deal found 4/29$314
This Trip.com deal was found by Cheapflights users on 4/29. 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.
Wed 5/213:50 pmYYZ - ORD
1 stop3h 47mWestJet
Thu 5/227:10 amORD - YYZ
1 stop3h 15mWestJet
Deal found 4/29$315

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 May 1, 2025.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Toronto

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 5/24

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Wed 5/28

9:40 am-12:22 pm

Nonstop1h 42m

$176

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/12

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Sun 6/15

9:40 am-12:22 pm

Nonstop1h 42m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/5

6:15 am-9:52 am

1 stop4h 37m

Chicago O'Hare Intl

Sun 6/8

9:14 pm-11:58 pm

Nonstop1h 44m

$187

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 6/19

7:25 am-11:24 am

1 stop4h 59m

Chicago O'Hare Intl

Mon 6/23

2:16 pm-8:36 pm

1 stop5h 20m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/21

4:05 pm-4:54 pm

Nonstop1h 49m

Chicago Midway

Sun 5/25

5:50 pm-8:32 pm

Nonstop1h 42m

$206

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/5

3:14 pm-4:09 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 6/8

5:00 am-10:21 am

1 stop4h 21m

$228

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/29

2:10 pm-3:05 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 6/2

9:08 pm-12:30 pm

1 stop14h 22m

$247

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 6/5

6:30 am-12:28 pm

1 stop6h 58m

Chicago Midway

Wed 6/11

9:24 am-5:15 pm

1 stop6h 51m

$260

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/5

6:30 am-12:41 pm

1 stop7h 11m

Chicago O'Hare Intl

Fri 6/6

1:45 pm-10:58 pm

1 stop8h 13m

$264

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/29

7:00 am-7:59 am

Nonstop1h 59m

Chicago O'Hare Intl

Thu 6/5

10:00 am-12:42 pm

Nonstop1h 42m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 39 results
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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 May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star
oojoPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 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 eDreams the most. eDreams 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.

The best insider tips for Toronto to Chicago 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 Toronto to Chicago trip
Airports
YYZ

Security lines at YYZ are efficient and fast. Arrive early for US flights as you'll clear customs before boarding.

Read more about YYZby Kaitlyn McInnis
ORD

At ORD, take the 'L' train for a quick and reliable trip to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
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 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

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 April 25, 2025.

To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 81 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 May 1, 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 50% 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 May 1, 2025.

The most flights from YTO to CHI are scheduled on a Wednesday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 May 1, 2025.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Porter Airlines, Delta 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.
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.8

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.8

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,934 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.8

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
KLM
7.8
Good
1,334 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.8

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.8

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Aeromexico
7.5
Good
1,698 reviews
Porter Airlines
8.0
Very good
285 reviews

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.8

Comfort

8.1

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 Porter Airlines. Our recent data shows that you can find tickets from as low as $176 on this airline. Additional options worth looking into are Air Transat and Air Canada, starting at $179 and $187 round-trip. Porter Airlines is currently priced 35% 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 $119. Users have also found prices from $120 and $123 on Porter Airlines and American 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 Copa Airlines (90%), Egyptair (89%) or ANA (85%) 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 $491, our data indicates the cheapest price to be $124. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $212.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$170Average$264FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$202Average$284FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$225Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$230Average$329FlexibilityNo cancel feeOn-time71%

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