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Cheap flights from Toronto to Chicago from £98

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 24/1. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
22 1월 — 29 1월1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Toronto to Chicago are usually found in July or June, booked 78 days in advance, depart on a Friday or Saturday and return on a Monday

Cheap flight deals from Toronto to Chicago

Enter your travel dates to find the best prices.

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 23 12월 2025.

일 28/1217:30YYZ - ORD
Nonstop2h 20mUnited Airlines
금 30/110:52ORD - YYZ
1 stop5h 57mUnited Airlines
Deal found 20/12£310
화 30/1218:30YYZ - ORD
2 stops16h 06mWestJet
일 8/208:50ORD - YYZ
2 stops20h 23mWestJet
Deal found 22/12£320
수 31/1219:40YYZ - ORD
1 stop5h 04mUnited Airlines
일 4/121:20ORD - YYZ
Nonstop1h 39mUnited Airlines
Deal found 22/12£358
화 30/1217:30YYZ - ORD
Nonstop2h 20mUnited Airlines
금 2/113:24ORD - YYZ
1 stop9h 22mUnited Airlines
Deal found 20/12£373
금 26/1212:05YYZ - ORD
Nonstop1h 56mUnited Airlines
월 5/114:00ORD - YYZ
1 stop7h 17mUnited Airlines
Deal found 22/12£376
월 29/1217:15YYZ - ORD
1 stop16h 46mWestJet
목 1/107:00ORD - YYZ
1 stop3h 19mWestJet
Deal found 22/12£381
금 26/1206:50YYZ - ORD
Nonstop2h 13mUnited Airlines
화 6/120:45ORD - YYZ
Nonstop1h 35mUnited Airlines
Deal found 22/12£383
화 30/1217:10YYZ - ORD
1 stop23h 11mWestJet
목 1/107:00ORD - YYZ
1 stop3h 19mWestJet
Deal found 22/12£390

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 23 12월 2025.

Round-trip from

£137

One-way from

£98

Popular in

December

Cheapest in

July

Average price

£242

Good round-trip deal

£783 or less

Good one-way deal

£81 or less
4/2-11/2
  • 4/2-11/2
  • 2 total stops
  • 30h 29m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 21/1
  • Nonstop
  • 2h 05m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (£15 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease (£5 potential savings vs. average return price).
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Average for round-trip flights in December 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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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 23 12월 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

일 15/2

06:30-11:45

1 stop6h 15m

Chicago O'Hare Intl

목 26/2

06:30-11:18

1 stop3h 48m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

화 13/1

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

수 14/1

21:15-23:59

Nonstop1h 44m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

토 14/2

17:15-20:44

1 stop4h 29m

Chicago O'Hare Intl

일 22/2

06:15-15:59

1 stop8h 44m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

목 5/2

07:45-13:13

1 stop6h 28m

Chicago O'Hare Intl

일 8/2

10:35-16:12

1 stop4h 37m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

수 18/2

06:15-09:41

1 stop4h 26m

Chicago O'Hare Intl

화 24/2

14:05-19:09

1 stop4h 04m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

목 19/2

17:10-22:05

1 stop5h 55m

Chicago O'Hare Intl

목 26/2

06:30-11:18

1 stop3h 48m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

화 17/2

10:05-13:20

1 stop4h 15m

Chicago O'Hare Intl

일 22/2

10:35-16:10

1 stop4h 35m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

수 18/2

10:05-13:20

1 stop4h 15m

Chicago O'Hare Intl

일 22/2

10:35-16:10

1 stop4h 35m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

화 17/2

10:05-13:20

1 stop4h 15m

Chicago O'Hare Intl

월 23/2

09:35-16:14

1 stop5h 39m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

토 14/2

17:15-20:44

1 stop4h 29m

Chicago O'Hare Intl

월 23/2

06:30-11:18

1 stop3h 48m

£158

Flights are sorted by cheapest return flights first.

Deals found on 21/12

Showing 1-10 of 33 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 19 December 2025.

Booking 78 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, April is the cheapest month in which you can book a flight from Toronto to Chicago (average of £61). Flying from Toronto to Chicago in February is currently the most expensive (average of £137). 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 23 12월 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 at midday, which can drop the price by up to 37% versus 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 return from Toronto to Chicago. Price data was last updated on 20 December 2025.

Travellers seeking maximum savings on their Toronto to Chicago flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday 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 23 12월 2025.

The most flights from YTO to CHI are scheduled on a Sunday (74 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (36 on average).

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

How often are flights from Toronto to Chicago delayed?

About 11% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.

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

Historically, flights departing at night 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?

Tuesday tends to have the lowest number of delays on this route, whereas Saturday 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 past year, United Airlines have had the lowest number of delays on this route, with just 6% of flights being delayed.

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 5h 10m. Delta provides one of the quickest options available for as low as £208. Airlines will cover a distance of 445 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 27% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Most travelers choose Toronto Pearson Intl - Chicago O'Hare Intl, Hamilton - Chicago O'Hare Intl or Toronto Island - 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%), Japan Airlines (80%) and Egyptair (78%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £326. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for £137 on average, our data indicates £1,065 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, April is the cheapest month in which you can book a flight from Toronto to Chicago (average of £61). Flying from Toronto to Chicago in February is currently the most expensive (average of £137). 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

Browse thousands of different options on Cheapflights for your next trip

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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 23 12월 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£137Average£170FlexibilityNo 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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