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$43+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
Nov 5 — Nov 121
Tue 11/5
Tue 11/12
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 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 October 31, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

October

Cheapest in

April

Round-trip from

$214
(Mytrip)

One-way from

$43
(123 Milhas)
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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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 October 31, 2024.

This FlightHub deal was found by Cheapflights users on 10/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/279:30 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 12/412:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$225
This Air Canada deal was found by Cheapflights users on 10/30. 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.
Wed 12/412:20 pmYYZ - ORD
Nonstop1h 51mAir Canada
Sat 12/77:18 amORD - YYZ
Nonstop1h 40mAir Canada
Deal found 10/30$239
This Air Canada deal was found by Cheapflights users on 10/30. 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.
Tue 12/1010:25 amYTZ - ORD
1 stop5h 20mAir Canada
Wed 12/252:01 pmORD - YTZ
1 stop4h 49mAir Canada
Deal found 10/30$244
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Wed 12/412:20 pmYYZ - ORD
1 stop7h 16mUnited Airlines
Sat 12/712:52 pmORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 10/30$245
This Flightnetwork deal was found by Cheapflights users on 10/30. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/213:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
Sun 11/2411:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 10/30$246
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Sun 12/88:00 amYYZ - ORD
Nonstop1h 57mMultiple Airlines
Wed 12/118:48 amORD - YYZ
1 stop4h 30mMultiple Airlines
Deal found 10/30$250
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/166:15 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Thu 12/266:00 amORD - YYZ
1 stop4h 53mAmerican Airlines
Deal found 10/30$261
This Delta deal was found by Cheapflights users on 10/30. 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.
Wed 12/412:15 pmYYZ - MDW
1 stop5h 47mDelta
Sat 12/75:50 pmMDW - YYZ
1 stop3h 46mDelta
Deal found 10/30$265
This FlightHub deal was found by Cheapflights users on 10/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/289:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sat 11/3012:55 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 10/30$282
This Delta deal was found by Cheapflights users on 10/30. 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.
Wed 12/45:05 pmYYZ - ORD
1 stop6h 38mDelta
Sat 12/75:20 pmORD - YYZ
1 stop4h 16mDelta
Deal found 10/30$285
This FlightHub deal was found by Cheapflights users on 10/31. 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 12/76:30 amYYZ - MDW
1 stop13h 02mWestJet
Tue 12/1012:44 pmMDW - YYZ
1 stop5h 22mWestJet
Deal found 10/31$305
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Wed 12/43:00 pmYTZ - ORD
1 stop9h 07mMultiple Airlines
Mon 12/94:19 pmORD - YTZ
1 stop15h 11mMultiple Airlines
Deal found 10/30$311

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 2,570,725 searches. Data last updated October 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/29

9:30 am-10:20 am

Nonstop1h 50m

$140

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 11/27

9:00 pm-10:07 pm

Nonstop2h 07m

$144

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 11/27

8:50 am-12:58 pm

1 stop5h 08m

$144

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/4

7:30 am-8:15 pm

1 stop13h 45m

$154

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 12/23

3:50 pm-4:40 pm

Nonstop1h 50m

$156

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 11/25

6:00 am-12:49 pm

1 stop7h 49m

$161

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 12/7

6:30 am-6:32 pm

1 stop13h 02m

$182

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 12/30

7:35 am-4:54 pm

1 stop10h 19m

$192

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/29

8:00 am-8:57 am

Nonstop1h 57m

$153

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 11/13

8:00 pm-7:55 am

1 stop12h 55m

$154

Flights are sorted by cheapest first

Deals found on 10/30

Showing 1-10 of 30 results
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2
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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 October.
ProviderPrice AccuracyTrust Score*Cancellation Policy
ExpediaPrice Accuracy1 starTrust Score*3 starsCancellation PolicyAirline Policy
eDreamsPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
FlightHubPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy
SmartFaresPrice Accuracy2 starsTrust Score*3 starsCancellation PolicyAirline Policy
Booking.comPrice Accuracy3 starsTrust Score*3 starsCancellation PolicyAirline Policy

*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 October 25, 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.

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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 October 31, 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 9% on your trip compared to booking a flight in the afternoon.

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 October 27, 2024.

Travelers seeking maximum savings on their Toronto to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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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 October 31, 2024.
Read through reviews of airlines operating flights from Toronto to Chicago, such as United Airlines, American Airlines and Air Canada. 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
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

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
8,835 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

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
294 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

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
387 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

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
9,240 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

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
2,804 reviews
Delta
8.0
Very good
8,835 reviews

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Overall

8.0

Entertainment

7.9

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.

  • Can I find flights from Toronto to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Toronto to Chicago for under $300. The cheapest flight booked recently is on Porter Airlines for just $214, but on average you can expect to pay $340.

  • Are there nonstop flights from Toronto to Chicago for under $300 on Cheapflights?

    Cheapflights has at least 7 direct flights from Toronto to Chicago under $300. A good price for a nonstop flight from Toronto to Chicago is less than $255.

  • Are there last-minute flights available from Toronto to Chicago for under $300?

    There are currently 14+ open flights from Toronto to Chicago within the next 7 days for less than $300.

  • What days are nonstop flights available from Toronto to Chicago?

    Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

  • How many flights depart from Toronto to Chicago on average per day?

    41 flight departures from Toronto to Chicago per day on average.
    Early Morning (Midnight to 6am) - 12% of flight departures
    Morning (6am - Noon) - 24% of flight departures
    Afternoon (Noon - 6pm) - 54% of flight departures
    Evening (6pm - Midnight) - 10% of flight departures

  • How long is the flight from Toronto to Chicago?

    Porter Airlines, Air Canada, and United Airlines can get you from Toronto to Chicago in just under 1h 50m. Your travel time can differ by up to 5h 26m. There are 437 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 $214 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $239 and $245 round-trip. Porter Airlines is currently priced 19% 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 $43. Users have also found prices from $127 and $144 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 (93%), Japan Airlines (91%) or Royal Jordanian (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 $1,019, our data indicates the cheapest price to be $146. The most popular route (Toronto Pearson Intl - Chicago O'Hare Intl), is priced around $239.

  • What does YYZ to ORD mean?

    Great question - YYZ to ORD just means Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Toronto to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Toronto to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Toronto to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Toronto to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Toronto to Chicago that allow pets onboard?

    Many airlines flying from Toronto to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Toronto to Chicago?

    Yes, you can often find last-minute deals on Toronto to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Toronto to Chicago flight deals updated?

    The Toronto to Chicago flight deals you see on this page were last updated on 10/30.

  • 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 2,570,725 searches. Data last updated October 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$205Average$256FlexibilityNo cancel feeOn-time52%
Air CanadaCheapest$207Average$312FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$219Average$290FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$236Average$326FlexibilityNo cancel feeOn-time71%
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