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$106+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from Toronto to Chicago are usually found in June or April, booked 52 days in advance, depart on a Friday or Saturday 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 julio 29, 2025.

Round-trip from

$148
(Trip.com)

One-way from

$106
(American Airlines)

Popular in

December

Cheapest in

June

Average price

$270

Good round-trip deal

$170 or less

Good one-way deal

$101 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 ($21 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 July 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 julio 29, 2025.

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.
vie. 8/227:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
sáb. 9/69:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/26$148
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/47:00 amYYZ - ORD
Nonstop1h 59mLufthansa
dom. 9/77:10 amORD - YYZ
Nonstop1h 48mLufthansa
Deal found 7/27$150
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/277:50 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
mar. 9/305:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 7/27$150
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/199:00 pmYYZ - ORD
Nonstop2h 07mUnited Airlines
lun. 9/2211:40 amORD - YYZ
1 stop4h 39mUnited Airlines
Deal found 7/27$151
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/2712:05 pmYYZ - ORD
2 stops9h 11mAir Canada
mié. 9/38:25 pmORD - YYZ
Nonstop1h 43mAir Canada
Deal found 7/27$152
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/257:55 amYTZ - MDW
Nonstop1h 50mAir Transat
mar. 8/265:20 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 7/26$154
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/123:25 pmYTZ - ORD
1 stop5h 57mAir Canada
sáb. 10/1810:40 amORD - YTZ
1 stop5h 05mAir Canada
Deal found 7/27$165
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/107:35 amYYZ - ORD
1 stop7h 31mAmerican Airlines
mié. 9/176:00 amORD - YYZ
1 stop5h 04mAmerican Airlines
Deal found 7/27$186
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/102:50 pmYYZ - MDW
1 stop4h 47mDelta
mié. 9/179:20 amMDW - YYZ
1 stop8h 08mDelta
Deal found 7/26$213
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/1212:15 pmYYZ - ORD
1 stop6h 59mDelta
mié. 10/1510:30 amORD - YYZ
1 stop3h 48mDelta
Deal found 7/27$220
This Justfly.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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/276:00 amYYZ - MDW
1 stop12h 35mWestJet
mar. 9/309:20 amMDW - YYZ
1 stop8h 08mWestJet
Deal found 7/27$276
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/27:30 pmYTZ - ORD
2 stops21h 40mMultiple Airlines
sáb. 9/610:40 amORD - YTZ
1 stop5h 05mMultiple Airlines
Deal found 7/28$279

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 julio 29, 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

vie. 8/22

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

sáb. 9/6

9:35 am-12:17 pm

Nonstop1h 42m

$148

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 9/4

7:00 am-7:59 am

Nonstop1h 59m

Chicago O'Hare Intl

dom. 9/7

7:10 am-9:58 am

Nonstop1h 48m

$150

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 9/27

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

mar. 9/30

5:20 pm-8:02 pm

Nonstop1h 42m

$150

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 9/19

9:00 pm-10:07 pm

Nonstop2h 07m

Chicago O'Hare Intl

lun. 9/22

11:40 am-5:19 pm

1 stop4h 39m

$151

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mié. 8/27

12:05 pm-8:16 pm

2 stops9h 11m

Chicago O'Hare Intl

mié. 9/3

8:25 pm-11:08 pm

Nonstop1h 43m

$152

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lun. 8/25

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

mar. 8/26

5:20 pm-8:02 pm

Nonstop1h 42m

$154

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

dom. 10/12

3:25 pm-8:22 pm

1 stop5h 57m

Chicago O'Hare Intl

sáb. 10/18

10:40 am-4:45 pm

1 stop5h 05m

$165

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mié. 9/10

7:35 am-2:06 pm

1 stop7h 31m

Chicago O'Hare Intl

mié. 9/17

6:00 am-12:04 pm

1 stop5h 04m

$186

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

mié. 9/10

2:50 pm-6:37 pm

1 stop4h 47m

Chicago Midway

mié. 9/17

9:20 am-6:28 pm

1 stop8h 08m

$213

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom. 10/12

12:15 pm-6:14 pm

1 stop6h 59m

Chicago O'Hare Intl

mié. 10/15

10:30 am-3:18 pm

1 stop3h 48m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 30 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 July 25, 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 julio 29, 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 36% 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 julio 29, 2025.

The most flights from YTO to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (37 on average).

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 julio 29, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta, and Air Transat 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
317 reviews

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,979 reviews
Porter Airlines
8.0
Very good
317 reviews

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
317 reviews

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,896 reviews
Porter Airlines
8.0
Very good
317 reviews

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
317 reviews

Overall

8.0

Food

7.6

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 $148 on this airline. Additional options worth looking into are Lufthansa and United Airlines, starting at $150 and $151 round-trip. Porter Airlines is currently priced 43% 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 American Airlines. According to our data, you can fly for as low as $106. Users have also found prices from $106 and $107 on Air Transat 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 Midway and Toronto Pearson Intl - Chicago Midway.

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

    Consider Cathay Pacific (100%), SkyWest Airlines (91%) or Egyptair (90%) 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 $2,979, our data indicates the cheapest price to be $122. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $142.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 julio 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$155Average$270FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$158Average$257FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$165Average$289FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$211Average$334FlexibilityNo cancel feeOn-time71%

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