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$125+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Jun 2 — Jun 91
Tue 6/2
Tue 6/9
1 adult, Economy
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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”

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

Cheap flight deals from Toronto to Chicago

Cheapest flights from Toronto to Chicago
Explore the most affordable flight options available from Toronto to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 3, 2026.

This FlightHub deal was found by Cheapflights users on 5/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:40 pm
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 9/1311:45 am
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/2$203
This FlightHub deal was found by Cheapflights users on 5/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:40 pm
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sat 9/197:00 am
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/2$204
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 5/273:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/29$205
This FlightHub deal was found by Cheapflights users on 5/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:05 am
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Tue 9/227:00 am
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/2$205
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.
Fri 5/224:00 pm
YYZ
-
ORD
Nonstop1h 59m
Air Canada
Tue 5/269:55 am
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 4/30$206
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/313:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/29$206
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:40 pm
YYZ
-
ORD
Nonstop2h 00m
Air Canada
Thu 5/289:55 am
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Deal found 4/29$207
This Justfly.com deal was found by Cheapflights users on 4/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 7/1810:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/28$207
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:30 am
YTZ
-
ORD
1 stop7h 23m
Air Canada
Wed 6/37:25 am
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 4/29$207
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:50 am
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Fri 5/297:09 am
ORD
-
YYZ
Nonstop1h 45m
United Airlines
Deal found 4/29$208
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 5/3110:30 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 4/29$208
This Mytrip deal was found by Cheapflights users on 5/3. 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 9/178:40 pm
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Mon 9/217:00 am
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 5/3$208

Find flight deals from Toronto to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto (YTO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(FlightHub)

One-way from

$125
(iWofly)

Popular in

April

Cheapest in

July

Average price

$254

Good round-trip deal

$190 or less

Good one-way deal

$94 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. 8% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Toronto (YTO) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto (YTO) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 3, 2026.
Use the filters below to find and compare flights from Toronto to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 5/25

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Tue 5/26

3:20 pm-6:00 pm

Nonstop1h 40m

$205

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 7/18

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Sat 7/25

10:25 am-1:05 pm

Nonstop1h 40m

$206

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 5/19

11:00 am-12:03 pm

Nonstop2h 03m

Chicago O'Hare Intl

Tue 6/9

9:15 pm-11:59 pm

Nonstop1h 44m

$209

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 9/11

1:40 pm-2:35 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sun 9/13

11:45 am-2:25 pm

Nonstop1h 40m

$209

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 5/23

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Fri 6/5

10:15 am-12:55 pm

Nonstop1h 40m

$220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/24

8:55 am-9:45 am

Nonstop1h 50m

Chicago Midway

Sun 5/31

3:20 pm-6:00 pm

Nonstop1h 40m

$220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/6

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Sun 8/9

10:25 am-1:05 pm

Nonstop1h 40m

$220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 8/23

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Sat 8/29

10:25 am-1:05 pm

Nonstop1h 40m

$224

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 6/5

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Sun 6/7

10:15 am-12:55 pm

Nonstop1h 40m

$225

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/27

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Sat 5/30

10:30 am-1:10 pm

Nonstop1h 40m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toronto to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toronto-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Toronto to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Toronto to Chicago

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

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

What is the cheapest 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 $228). Flying from Toronto to Chicago in December is currently the most expensive (average of $935). 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 3, 2026.

A simple way to save on the total cost of your ticket is to fly from Toronto to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 32% on your trip compared to booking a flight in the evening.

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 April 25, 2026.

Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Saturday at noon 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 3, 2026.

The most flights from YTO to CHI are scheduled on a Friday (75 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (57 on average).

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

How often are flights from Toronto to Chicago delayed?

About 13% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 137 minutes.

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

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

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

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

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

Over the last year, United Airlines have had the lowest number of delays on this route, with just 8% of flights being delayed.

The best insider tips for Toronto to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Toronto to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYZ

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 3, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,Air Transat, andUnited Airlines from Toronto to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
436 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
436 reviews
Porter Airlines
8.0
Very good
436 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Transat
7.8
Good
546 reviews
Porter Airlines
8.0
Very good
436 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,683 reviews
Porter Airlines
8.0
Very good
436 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
American Airlines
7.1
Good
11,674 reviews
Porter Airlines
8.0
Very good
436 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,993 reviews
Porter Airlines
8.0
Very good
436 reviews

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

Related info for your journey

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

  • How long is the flight from Toronto to Chicago?

    Porter Airlines, United Airlines, and Delta can get you from Toronto to Chicago in just under 1h 50m. Your travel time can differ by up to 2h 29m. There are 442 mi between Toronto and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Our cheapest airline available from Toronto to Chicago is Porter Airlines. Our recent data shows that you can find tickets from as low as $80 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $146 and $165 round-trip. Porter Airlines is currently priced 68% 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 $111 and $122 on United Airlines and Porter Airlines, respectively.

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

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

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

    Consider EVA Air (100%), Copa Airlines (89%) or Japan Airlines (75%) 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 $569, our data indicates the cheapest price to be $125. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $209.

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

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of $228). Flying from Toronto to Chicago in December is currently the most expensive (average of $935). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

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

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Top 4 airlines flying from Toronto to Chicago

Discover the top 4 airlines that operate flights from Toronto to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$80Average$350FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$146Average$280FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$165Average$267FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$292FlexibilityNo cancel feeOn-time71%

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