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Cheap flights from Toronto to Chicago from £83

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 19/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
8 Sep — 15 Sep1
1 adult

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 85 days in advance, depart on a Thursday or Friday 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 3 September 2025.

Round-trip from

£109

One-way from

£83

Popular in

December

Cheapest in

July

Average price

£186

Good round-trip deal

£524 or less

Good one-way deal

£345 or less
United Airlines
  • United Airlines
  • 14/11-16/11
  • Nonstop
  • 3h 49m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 19/10
  • Nonstop
  • 1h 58m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 7% potential increase in price (£10 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
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Average for round-trip flights in September 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 3 September 2025.

Fri 14/1106:52YYZ - ORD
Nonstop2h 06mUnited Airlines
Sun 16/1113:19ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 1/9£109
Sat 25/1017:15YYZ - ORD
Nonstop2h 07mUnited Airlines
Sat 1/1113:19ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 1/9£118
Tue 25/1119:40YYZ - ORD
1 stop5h 03mUnited Airlines
Sat 29/1118:28ORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 2/9£121
Thu 16/1008:15YYZ - ORD
Nonstop1h 54mAir Canada
Thu 23/1009:55ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 1/9£121
Wed 15/1014:10YYZ - ORD
Nonstop1h 54mAir Canada
Wed 22/1009:55ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 2/9£124
Tue 25/1108:55YYZ - ORD
Nonstop2h 05mUnited Airlines
Mon 1/1213:19ORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 2/9£124
Sat 25/1014:45YYZ - ORD
Nonstop2h 03mUnited Airlines
Wed 29/1007:10ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 1/9£128
Fri 17/1008:15YYZ - ORD
Nonstop1h 54mAir Canada
Fri 24/1010:40ORD - YYZ
1 stop5h 44mAir Canada
Deal found 3/9£130
Sat 22/1112:05YYZ - ORD
Nonstop1h 56mAir Canada
Thu 27/1108:00ORD - YYZ
Nonstop1h 40mAir Canada
Deal found 2/9£131
Fri 7/1108:55YYZ - ORD
Nonstop2h 05mUnited Airlines
Tue 11/1113:00ORD - YYZ
1 stop9h 46mUnited Airlines
Deal found 31/8£133
Sat 4/1015:25YTZ - ORD
1 stop5h 46mAir Canada
Wed 15/1008:40ORD - YTZ
1 stop5h 05mAir Canada
Deal found 2/9£154
Fri 17/1020:25YTZ - ORD
1 stop14h 26mAir Canada
Fri 24/1010:40ORD - YTZ
1 stop6h 05mAir Canada
Deal found 2/9£162

Cheapflights Fare Finder

 
Customise 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 858,174 searches. Data last updated 3 September 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

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 14/11

06:52-07:58

Nonstop2h 06m

Chicago O'Hare Intl

Sun 16/11

13:19-16:02

Nonstop1h 43m

£109

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 28/10

11:00-12:05

Nonstop2h 05m

Chicago O'Hare Intl

Sat 1/11

21:20-23:59

Nonstop1h 39m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 25/10

17:15-18:22

Nonstop2h 07m

Chicago O'Hare Intl

Sat 1/11

13:19-16:02

Nonstop1h 43m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/10

09:00-10:05

Nonstop2h 05m

Chicago O'Hare Intl

Sun 2/11

07:10-09:58

Nonstop1h 48m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 29/10

15:30-16:52

Nonstop2h 22m

Chicago O'Hare Intl

Sat 1/11

13:19-16:02

Nonstop1h 43m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 28/10

09:00-10:05

Nonstop2h 05m

Chicago O'Hare Intl

Sun 2/11

21:20-23:59

Nonstop1h 39m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 27/10

17:30-18:39

Nonstop2h 09m

Chicago O'Hare Intl

Sat 1/11

18:28-21:21

Nonstop1h 53m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 25/10

09:00-09:55

Nonstop1h 55m

Chicago O'Hare Intl

Sun 2/11

21:20-23:59

Nonstop1h 39m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 27/10

17:30-18:39

Nonstop2h 09m

Chicago O'Hare Intl

Sun 2/11

21:20-23:59

Nonstop1h 39m

£118

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

19:40-23:43

1 stop5h 03m

Chicago O'Hare Intl

Sat 29/11

07:10-09:58

Nonstop1h 48m

£121

Flights are sorted by cheapest return flights first.

Deals found on 3/9

Showing 1-10 of 42 results
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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 return 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 return flight from Toronto to Chicago. Price data was last updated on 29 August 2025.

Booking 85 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of £595). Flying from Toronto to Chicago in July is currently the most expensive (average of £843). 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 3 September 2025.

When flying from Toronto to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 48% versus a flight at midday.

What is the cheapest day to fly from Toronto to Chicago?

Use this chart to determine the cheapest time to fly return from Toronto to Chicago. Price data was last updated on 31 August 2025.

Travellers seeking maximum savings on their Toronto to Chicago flight should consider departing on Thursday mornings when fares are most often at their lowest. Saturday at midday 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 3 September 2025.

The most flights from YTO to CHI are scheduled on a Tuesday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

How much does it cost for a return flight from Toronto to Chicago?

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?

    A quick flight from Toronto to Chicago can take about 2h 06m. United Airlines provides one of the quickest options available for as low as £109. Airlines will cover a distance of 436 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Toronto to Chicago round-trip?

    Flying on Air Canada is currently your cheapest option to Chicago, with prices starting at £137. Air Canada is 28% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Toronto to Chicago one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as £83. However, be on the lookout for offers from Air Canada and WestJet, as they are both options that can get you from Toronto to Chicago for a low price.

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

    Most travelers choose Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago O'Hare Intl or Hamilton - Chicago O'Hare Intl when deciding on the best route from Toronto to Chicago.

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

    The top 3 most reliable airlines when flying from Toronto to Chicago are EVA Air (83%), SkyWest Airlines (83%) and ANA (83%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £151. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £130 on average our data indicates £465 when flying from Toronto to Chicago.

  • 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 holiday 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, January is the cheapest month in which you can book a flight from Toronto to Chicago (average of £595). Flying from Toronto to Chicago in July is currently the most expensive (average of £843). 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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Alternative routes for Toronto to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights

Top airline flying from Toronto to Chicago

Discover the top airline 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 858,174 searches. Data last updated 3 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£137Average£188FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Toronto to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Toronto to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Toronto to Chicago?

Cheapflights simply makes it quick and affordable to book flights from Toronto to Chicago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Toronto to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Toronto shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Toronto to Chicago become cheaper?

Yes! Start tracking prices for Toronto to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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