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Cheap flights from Toronto to Chicago from £102

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
5 Sep — 12 Sep1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in September or February, booked 88 days in advance, depart on a Friday or Wednesday and return on a Tuesday

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 6 August 2026.

Sat 5/907:00 -
Nonstop2h 00m
Sun 13/917:35 -
Nonstop1h 43m
Deal found 3/8£149
Thu 17/910:45 -
1 stop5h 07m
Thu 24/914:00 -
Nonstop1h 42m
Deal found 5/8£149
Thu 17/908:05 -
Nonstop1h 55m
Thu 24/909:55 -
Nonstop1h 45m
Deal found 5/8£151
Tue 1/921:00 -
Nonstop2h 05m
Tue 8/908:45 -
1 stop5h 48m
Deal found 2/8£155
Fri 2/1021:00 -
Nonstop2h 06m
Mon 5/1008:50 -
1 stop9h 12m
Deal found 3/8£157
Fri 11/916:00 -
1 stop5h 12m
Thu 17/911:05 -
1 stop6h 07m
Deal found 2/8£163
Wed 16/908:50 -
Nonstop2h 03m
Sun 20/911:05 -
1 stop6h 07m
Deal found 4/8£163
Fri 6/1116:35 -
Nonstop1h 55m
Tue 10/1118:10 -
Nonstop1h 40m
Deal found 3/8£163
Mon 14/921:00 -
Nonstop2h 05m
Wed 16/908:45 -
1 stop9h 17m
Deal found 3/8£170
Thu 10/911:00 -
Nonstop2h 00m
Sun 13/920:40 -
Nonstop1h 46m
Deal found 3/8£172
Tue 15/921:00 -
Nonstop2h 05m
Thu 17/911:05 -
1 stop6h 07m
Deal found 1/8£173
Mon 28/912:15 -
Nonstop2h 06m
Wed 30/912:55 -
1 stop4h 56m
Deal found 3/8£198

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 6 August 2026.

Round-trip from

£149

One-way from

£102

Popular in

May

Cheapest in

September

Average price

£205

Good round-trip deal

£336 or less

Good one-way deal

£90 or less
Air Canada
  • Air Canada
  • 5/9-13/9
  • Nonstop
  • 3h 43m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 15/9
  • Nonstop
  • 2h 06m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (£6 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).
Search Deals
Average for round-trip flights in August 2026
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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 6 August 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
Fastest return journey

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 6/11

16:35-17:30

Nonstop1h 55m

Chicago O'Hare Intl

Tue 10/11

18:10-20:50

Nonstop1h 40m

£163

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 2/10

19:43-23:32

1 stop4h 49m

Chicago O'Hare Intl

Mon 5/10

08:50-19:02

1 stop9h 12m

£168

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 8/9

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Tue 15/9

20:40-23:26

Nonstop1h 46m

£170

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 15/9

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Thu 17/9

11:05-18:12

1 stop6h 07m

£173

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 16/9

16:05-20:30

1 stop5h 25m

Chicago O'Hare Intl

Wed 23/9

08:55-17:20

1 stop7h 25m

£175

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 19/9

19:00-00:28

1 stop6h 28m

Chicago O'Hare Intl

Mon 21/9

06:25-14:19

1 stop6h 54m

£175

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 11/9

17:15-18:18

Nonstop2h 03m

Chicago O'Hare Intl

Mon 14/9

09:55-12:40

Nonstop1h 45m

£177

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 11/9

16:05-20:30

1 stop5h 25m

Chicago O'Hare Intl

Mon 14/9

17:10-22:59

1 stop4h 49m

£181

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 17/9

14:24-20:30

1 stop7h 06m

Chicago O'Hare Intl

Thu 24/9

13:55-22:59

1 stop8h 04m

£181

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 9/9

09:45-12:59

1 stop4h 14m

Chicago O'Hare Intl

Wed 16/9

17:10-22:59

1 stop4h 49m

£181

Flights are sorted by cheapest return flights first.

Deals found on 2/8

Showing 1-10 of 47 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

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 £187). Flying from Toronto to Chicago in December is currently the most expensive (average of £228). 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 6 August 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 38% versus a flight in the afternoon.

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 6 August 2026.

The most flights from YTO to CHI are scheduled on a Wednesday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

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

Airfare is below average for this route at the moment.
Toronto to Chicago flights typically cost between £166 and £252 in September.
The cheapest return price found within the last 5 days was £149 on Multiple Airlines (5 Sept–13 Sept).

How often are flights from Toronto to Chicago delayed?

About 14% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 135 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 Sunday 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 9% of flights being delayed.

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 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 13 June 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. Sunday at midday flights should be avoided if possible as fares are typically the most expensive at this time.

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. Porter Airlines provides one of the quickest options available for as low as £163. Airlines will cover a distance of 445 mi. This flight may include one or multiple stops.

  • 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 Egyptair (95%), Envoy Air (89%) and Japan Airlines (84%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £107. While the most popular route (Toronto Island - Chicago O'Hare Intl) can be booked for £268 on average, our data indicates £280 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 £187). Flying from Toronto to Chicago in December is currently the most expensive (average of £228). 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

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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