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$108+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Toronto to Chicago are usually found in April or May, booked 52 days in advance, depart on a Friday or Thursday and return on a Friday

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 June 12, 2025.

Round-trip from

$161
(iWofly)

One-way from

$108
(Air Canada)

Popular in

December

Cheapest in

April

Average price

$253

Good round-trip deal

$170 or less

Good one-way deal

$100 or less
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. 7% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This iWofly deal was found by Cheapflights users on 6/12. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/267:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 6/299:40 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 6/12$161
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/197:00 amYYZ - ORD
Nonstop1h 59mUnited Airlines
Mon 9/229:12 pmORD - YYZ
Nonstop1h 46mUnited Airlines
Deal found 6/12$164
This Air Canada deal was found by Cheapflights users on 6/12. 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 9/108:15 amYYZ - ORD
Nonstop1h 53mAir Canada
Fri 9/126:20 pmORD - YYZ
Nonstop1h 42mAir Canada
Deal found 6/12$165
This SmartFares deal was found by Cheapflights users on 6/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:55 amYTZ - MDW
Nonstop1h 50mAir Transat
Fri 9/129:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 6/11$186
This KAYAK deal was found by Cheapflights users on 6/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/303:45 pmYYZ - ORD
1 stop5h 42mAmerican Airlines
Thu 10/29:48 amORD - YYZ
1 stop6h 27mAmerican Airlines
Deal found 6/10$191
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
Mon 8/187:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 8/195:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 6/11$205
This Air Canada deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/410:25 amYTZ - ORD
1 stop5h 30mAir Canada
Wed 10/1510:40 amORD - YTZ
1 stop5h 05mAir Canada
Deal found 6/11$207
This Kissandfly.com deal was found by Cheapflights users on 6/11. 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 7/37:00 amYYZ - ORD
Nonstop1h 59mLufthansa
Mon 7/79:14 pmORD - YYZ
Nonstop1h 44mLufthansa
Deal found 6/11$209
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:15 pmYYZ - MDW
1 stop7h 21mDelta
Wed 10/159:30 amMDW - YYZ
1 stop6h 53mDelta
Deal found 6/11$213
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/45:04 pmYYZ - ORD
1 stop6h 17mDelta
Sun 7/69:00 amORD - YYZ
1 stop7h 15mDelta
Deal found 6/9$219
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Fri 7/254:00 pmYYZ - ORD
1 stop6h 30mMultiple Airlines
Fri 8/16:20 pmORD - YYZ
Nonstop1h 44mMultiple Airlines
Deal found 6/10$249
This Kissandfly.com deal was found by Cheapflights users on 6/12. 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.
Mon 7/217:25 pmYYZ - ORD
1 stop12h 58mPorter Airlines
Sun 7/275:55 pmORD - YYZ
Nonstop1h 49mPorter Airlines
Deal found 6/12$262

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 June 12, 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

Thu 6/26

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Sun 6/29

9:40 am-12:22 pm

Nonstop1h 42m

$161

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 9/19

7:00 am-7:59 am

Nonstop1h 59m

Chicago O'Hare Intl

Mon 9/22

9:12 pm-11:58 pm

Nonstop1h 46m

$164

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 9/10

8:15 am-9:08 am

Nonstop1h 53m

Chicago O'Hare Intl

Fri 9/12

6:20 pm-9:02 pm

Nonstop1h 42m

$165

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 8/30

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Fri 9/12

9:15 am-11:57 am

Nonstop1h 42m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 9/30

3:45 pm-8:27 pm

1 stop5h 42m

Chicago O'Hare Intl

Thu 10/2

9:48 am-5:15 pm

1 stop6h 27m

$191

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/18

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Tue 8/19

5:20 pm-8:02 pm

Nonstop1h 42m

$205

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 8/30

3:25 pm-8:16 pm

1 stop5h 51m

Chicago O'Hare Intl

Fri 9/12

10:40 am-4:45 pm

1 stop5h 05m

$207

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 7/3

7:00 am-7:59 am

Nonstop1h 59m

Chicago O'Hare Intl

Mon 7/7

9:14 pm-11:58 pm

Nonstop1h 44m

$209

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 10/4

12:15 pm-6:36 pm

1 stop7h 21m

Chicago Midway

Wed 10/15

9:30 am-5:23 pm

1 stop6h 53m

$213

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/4

5:04 pm-10:21 pm

1 stop6h 17m

Chicago O'Hare Intl

Sun 7/6

9:00 am-5:15 pm

1 stop7h 15m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 36 results
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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

Toronto Pearson offers fast security lines for US-bound flights, but arrive early to clear US customs before boarding.

Read more about YYZby Kaitlyn McInnis
ORD

At ORD, consider taking the “L” train to avoid traffic when heading to downtown Chicago.

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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from Toronto to Chicago, you should look to book at least 52 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 June 12, 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 42% 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 June 12, 2025.

The most flights from YTO to CHI are scheduled on a Wednesday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 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 June 12, 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
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
KLM
7.8
Good
1,358 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
396 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews

Boarding

8.2

Food

7.6

Crew

8.7

Comfort

8.1

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 $161 on this airline. Additional options worth looking into are United Airlines and Air Canada, starting at $164 and $165 round-trip. Porter Airlines is currently priced 39% 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 $108. Users have also found prices from $110 and $111 on Porter Airlines 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 SkyWest Airlines (98%), Republic Airways (92%) or Copa Airlines (91%) 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 $1,135, our data indicates the cheapest price to be $121. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $147.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$162Average$269FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$287FlexibilityNo cancel feeOn-time69%
Porter AirlinesCheapest$169Average$252FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$218Average$318FlexibilityNo cancel feeOn-time71%

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