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$143+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from Toronto to Chicago are usually found in April or February, booked 87 days in advance, depart on a Wednesday 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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

November

Cheapest in

April

Round-trip from

$228
(oojo)

One-way from

$143
(Air Canada)
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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High demand for flights, 14% potential price rise
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Best time to find cheap flights, 10% potential price drop
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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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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 November 20, 2024.

This oojo deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/123:50 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/1612:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/19$228
This Air Canada deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1112:00 pmYYZ - ORD
1 stop7h 41mAir Canada
Thu 12/127:19 amORD - YYZ
Nonstop1h 39mAir Canada
Deal found 11/18$237
This Air Canada deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/148:25 amYTZ - ORD
1 stop7h 20mAir Canada
Fri 1/1011:35 amORD - YTZ
1 stop5h 15mAir Canada
Deal found 11/18$241
This United Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1111:00 amYYZ - ORD
Nonstop1h 59mUnited Airlines
Thu 12/127:19 amORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 11/19$245
This Flysmarter deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:35 pmYYZ - ORD
Nonstop1h 57mLufthansa
Tue 12/178:48 amORD - YYZ
1 stop4h 30mLufthansa
Deal found 11/20$259
This Booking.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/123:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
Sun 12/155:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/19$260
This CheapTicketsDeal deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:30 amYYZ - MDW
1 stop13h 02mWestJet
Mon 12/169:38 amMDW - YYZ
1 stop12h 56mWestJet
Deal found 11/20$267
This Delta deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:30 amYYZ - ORD
1 stop9h 13mDelta
Thu 12/197:00 amORD - YYZ
1 stop8h 14mDelta
Deal found 11/19$274
This United deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/166:35 pmYYZ - ORD
Nonstop1h 57mMultiple Airlines
Thu 12/266:06 pmORD - YYZ
1 stop12h 59mMultiple Airlines
Deal found 11/20$278
This Trip.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/112:00 pmYYZ - ORD
1 stop9h 44mWestJet
Thu 12/1210:10 amORD - YYZ
1 stop5h 27mWestJet
Deal found 11/18$292
This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1210:05 amYYZ - MDW
1 stop7h 56mDelta
Mon 12/165:50 pmMDW - YYZ
1 stop3h 46mDelta
Deal found 11/20$294
This Kissandfly.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:15 amYYZ - ORD
Nonstop2h 15mBritish Airways
Wed 1/83:00 pmORD - YYZ
Nonstop1h 35mBritish Airways
Deal found 11/19$297

Find flights from Toronto to Chicago within your budget

Customize your flight search to find flights from Toronto to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

3:50 pm-4:40 pm

Nonstop1h 50m

Chicago Midway

Mon 12/16

12:05 pm-2:47 pm

Nonstop1h 42m

$228

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/11

12:00 pm-6:41 pm

1 stop7h 41m

Chicago O'Hare Intl

Thu 12/12

7:19 am-9:58 am

Nonstop1h 39m

$237

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 12/14

8:25 am-2:45 pm

1 stop7h 20m

Chicago O'Hare Intl

Fri 1/10

11:35 am-5:50 pm

1 stop5h 15m

$241

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/11

11:00 am-11:59 am

Nonstop1h 59m

Chicago O'Hare Intl

Thu 12/12

7:19 am-9:58 am

Nonstop1h 39m

$245

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

6:25 am-10:54 am

1 stop5h 29m

Chicago O'Hare Intl

Sun 12/15

7:19 am-9:58 am

Nonstop1h 39m

$259

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

3:50 pm-4:40 pm

Nonstop1h 50m

Chicago Midway

Sun 12/15

5:35 pm-8:17 pm

Nonstop1h 42m

$260

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

12:20 pm-1:11 pm

Nonstop1h 51m

Chicago O'Hare Intl

Sun 12/15

7:19 am-9:58 am

Nonstop1h 39m

$262

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/12

6:30 am-6:32 pm

1 stop13h 02m

Chicago Midway

Mon 12/16

9:38 am-11:34 pm

1 stop12h 56m

$267

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

6:30 am-2:43 pm

1 stop9h 13m

Chicago O'Hare Intl

Thu 12/19

7:00 am-4:14 pm

1 stop8h 14m

$274

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 12/12

10:05 am-5:01 pm

1 stop7h 56m

Chicago Midway

Mon 12/16

5:50 pm-10:36 pm

1 stop3h 46m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 35 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Toronto to Chicago

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

Travel insights for flights from Toronto to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on November 15, 2024.

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, September is the cheapest month in which you can book a flight from Toronto to Chicago (average of $232). Flying from Toronto to Chicago in June is currently the most expensive (average of $308). 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 November 20, 2024.

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 11% 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 November 18, 2024.

Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Wednesday 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 November 20, 2024.

The most flights from YTO to CHI are scheduled on a Monday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 November 20, 2024.
Read through reviews of airlines operating flights from Toronto to Chicago, such as Air Canada, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,756 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 10

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

Porter Airlines
7.8
Good
288 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 10

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

Air Transat
7.8
Good
389 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 10

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

United Airlines
7.4
Good
9,171 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 10

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

WestJet
7.3
Good
2,811 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Reviews

1 / 10

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

Related info for your journey

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

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

    Our cheapest airline available from Toronto to Chicago is Porter Airlines. Our recent data shows that you can find tickets from as low as $228 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $237 and $245 round-trip. Porter Airlines is currently priced 14% 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 $143. Users have also found prices from $143 and $147 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 Egyptair (100%), Jazz (100%) or Lufthansa (100%) 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 $894, our data indicates the cheapest price to be $145. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $240.

  • 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, September is the cheapest month in which you can book a flight from Toronto to Chicago (average of $232). Flying from Toronto to Chicago in June is currently the most expensive (average of $308). 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

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$157Average$280FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$205Average$255FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$219Average$288FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$327FlexibilityNo cancel feeOn-time71%
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