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Cheap flights from Toronto to Chicago from £96

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
6 Jun — 13 Jun1
1 adult
1 adult, Economy, 0 bags
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 Saturday and return on a Wednesday

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 7 May 2026.

Wed 27/508:50
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Mon 1/621:20
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 2/5£152
Tue 19/513:00
YYZ
-
ORD
Nonstop2h 01m
United Airlines
Mon 25/521:20
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 2/5£162
Fri 29/521:00
YYZ
-
ORD
Nonstop2h 05m
United Airlines
Sat 30/515:53
ORD
-
YYZ
1 stop7h 01m
United Airlines
Deal found 3/5£174
Thu 18/614:00
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Sat 20/614:15
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Deal found 5/5£177
Wed 17/609:45
YYZ
-
ORD
1 stop7h 41m
Delta
Wed 24/608:52
ORD
-
YYZ
1 stop3h 42m
Delta
Deal found 3/5£177
Sat 13/606:50
YTZ
-
ORD
1 stop5h 30m
Air Canada
Sat 20/614:00
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 3/5£177
Fri 29/519:43
YYZ
-
ORD
1 stop4h 43m
United Airlines
Mon 1/621:20
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 3/5£178
Fri 22/513:00
YYZ
-
ORD
Nonstop2h 06m
United Airlines
Mon 25/521:20
ORD
-
YYZ
Nonstop1h 39m
United Airlines
Deal found 2/5£182
Tue 21/719:20
YTZ
-
ORD
Nonstop1h 56m
Air Canada
Fri 24/714:00
ORD
-
YTZ
Nonstop1h 41m
Air Canada
Deal found 6/5£182
Wed 23/913:40
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 27/911:45
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/5£183
Wed 20/512:09
YYZ
-
ORD
1 stop6h 56m
Delta
Sun 24/513:44
ORD
-
YYZ
1 stop8h 15m
Delta
Deal found 2/5£187
Fri 17/716:00
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Wed 22/717:35
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 6/5£188

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 7 May 2026.

Round-trip from

£152

One-way from

£96

Popular in

April

Cheapest in

July

Average price

£187

Good round-trip deal

£172 or less

Good one-way deal

£127 or less
United Airlines
  • United Airlines
  • 12/6-14/6
  • Nonstop
  • 3h 45m total
  • Toronto to Chicago
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United Airlines
  • United Airlines
  • 4/6
  • Nonstop
  • 2h 04m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (£12 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£4 potential savings vs. average return 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).
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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 7 May 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 return flight

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 13/6

07:00-08:00

Nonstop2h 00m

Chicago O'Hare Intl

Sat 20/6

15:53-23:54

1 stop7h 01m

£174

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 13/6

14:24-20:31

1 stop7h 07m

Chicago O'Hare Intl

Sat 20/6

07:01-15:19

1 stop7h 18m

£177

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 18/6

12:09-18:29

1 stop7h 20m

Chicago O'Hare Intl

Sun 21/6

07:01-15:19

1 stop7h 18m

£178
Fastest return journey

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 23/9

13:40-14:35

Nonstop1h 55m

Chicago O'Hare Intl

Sun 27/9

11:45-14:25

Nonstop1h 40m

£183

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 24/10

10:05-11:00

Nonstop1h 55m

Chicago O'Hare Intl

Fri 30/10

16:15-18:57

Nonstop1h 42m

£183

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 17/6

14:29-18:29

1 stop5h 00m

Chicago O'Hare Intl

Sat 20/6

07:01-13:34

1 stop5h 33m

£196

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 29/5

14:30-19:09

1 stop5h 39m

Chicago O'Hare Intl

Mon 1/6

09:25-17:21

1 stop6h 56m

£196

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 8/6

12:45-23:26

1 stop11h 41m

Chicago O'Hare Intl

Thu 11/6

07:09-09:54

Nonstop1h 45m

£196

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 17/6

07:00-08:00

Nonstop2h 00m

Chicago O'Hare Intl

Sun 21/6

07:09-09:54

Nonstop1h 45m

£198

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 22/6

14:29-20:31

1 stop7h 02m

Chicago O'Hare Intl

Fri 26/6

17:22-23:02

1 stop4h 40m

£206

Flights are sorted by cheapest return flights first.

Deals found on 3/5

Showing 1-10 of 50 resultsSorted by cheapest first
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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?

Booking 87 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, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of £168). Flying from Toronto to Chicago in December is currently the most expensive (average of £688). 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 7 May 2026.

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 evening, which can drop the price by up to 61% versus 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 return from Toronto to Chicago. Price data was last updated on 2 May 2026.

Travellers 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 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 7 May 2026.

The most flights from YTO to CHI are scheduled on a Thursday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 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 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 past year, United Airlines have had the lowest number of delays on this route, with just 8% 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 1h 55m. United Airlines provides one of the quickest options available for as low as £183. 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 £135. 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 Island - Chicago O'Hare Intl, Toronto Pearson Intl - 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 (100%), Copa Airlines (89%) and Japan Airlines (75%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £110. While the most popular route (Toronto Island - Chicago O'Hare Intl) can be booked for £251 on average, our data indicates £399 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, August is the cheapest month in which you can book a flight from Toronto to Chicago (average of £168). Flying from Toronto to Chicago in December is currently the most expensive (average of £688). 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 7 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£135Average£187FlexibilityNo 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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