Find flights
Deals
When to book
FAQs

Cheap flights from Toronto to Chicago from £101

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — CHI
11 Sep — 18 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 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 12 August 2026.

Wed 16/919:35 -
Nonstop2h 06m
Mon 21/907:25 -
Nonstop1h 42m
Deal found 9/8£148
Tue 8/912:15 -
Nonstop2h 06m
Tue 15/908:45 -
1 stop6h 05m
Deal found 9/8£150
Wed 16/914:00 -
Nonstop1h 55m
Mon 21/915:45 -
Nonstop1h 46m
Deal found 9/8£151
Tue 8/914:00 -
Nonstop1h 55m
Tue 15/909:55 -
Nonstop1h 45m
Deal found 9/8£153
Thu 10/912:15 -
Nonstop2h 06m
Mon 14/907:25 -
Nonstop1h 42m
Deal found 11/8£154
Mon 14/911:00 -
Nonstop2h 00m
Mon 28/907:09 -
Nonstop1h 45m
Deal found 7/8£156
Mon 14/921:00 -
Nonstop2h 05m
Sat 19/921:18 -
Nonstop1h 41m
Deal found 10/8£162
Mon 14/921:00 -
Nonstop2h 05m
Fri 18/921:18 -
Nonstop1h 41m
Deal found 11/8£163
Thu 24/911:00 -
Nonstop2h 00m
Mon 28/915:40 -
1 stop5h 13m
Deal found 10/8£165
Tue 8/909:44 -
1 stop7h 45m
Mon 14/914:15 -
Nonstop1h 46m
Deal found 7/8£167
Mon 14/921:00 -
Nonstop2h 05m
Sat 19/915:40 -
1 stop5h 13m
Deal found 10/8£168
Mon 14/921:00 -
Nonstop2h 05m
Mon 21/911:05 -
1 stop6h 07m
Deal found 11/8£170

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 12 August 2026.

Round-trip from

£148

One-way from

£101

Popular in

July

Cheapest in

September

Average price

£206

Good round-trip deal

£327 or less

Good one-way deal

£90 or less
Air Canada
  • Air Canada
  • 16/9-21/9
  • Nonstop
  • 3h 48m total
  • Toronto to Chicago
Search Deals
United Airlines
  • United Airlines
  • 9/9
  • Nonstop
  • 2h 00m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (£6 potential increase over avg. return price).
Search Deals
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
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).
Search Deals

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 12 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

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 3/9

07:00-08:00

Nonstop2h 00m

Chicago O'Hare Intl

Tue 8/9

21:18-23:59

Nonstop1h 41m

£156

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 16/9

10:45-14:52

1 stop5h 07m

Chicago O'Hare Intl

Mon 21/9

11:05-17:50

1 stop5h 45m

£164

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

11:00-12:00

Nonstop2h 00m

Chicago O'Hare Intl

Sun 13/9

20:40-23:26

Nonstop1h 46m

£176

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

08:50-09:53

Nonstop2h 03m

Chicago O'Hare Intl

Sun 13/9

17:53-20:44

Nonstop1h 51m

£177

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 8/9

16:05-20:30

1 stop5h 25m

Chicago O'Hare Intl

Tue 15/9

07:05-11:18

1 stop3h 13m

£181

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 25/9

14:24-20:30

1 stop7h 06m

Chicago O'Hare Intl

Mon 28/9

08:55-17:20

1 stop7h 25m

£181

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 16/9

20:00-00:28

1 stop5h 28m

Chicago O'Hare Intl

Mon 21/9

08:42-14:19

1 stop4h 37m

£181

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

08:50-09:53

Nonstop2h 03m

Chicago O'Hare Intl

Sat 12/9

14:32-22:23

1 stop6h 51m

£183

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 10/9

20:00-00:28

1 stop5h 28m

Chicago O'Hare Intl

Mon 14/9

06:25-19:02

1 stop11h 37m

£187

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Wed 26/8

12:09-16:17

1 stop5h 08m

Chicago O'Hare Intl

Tue 8/9

13:55-22:59

1 stop8h 04m

£200

Flights are sorted by cheapest return flights first.

Deals found on 9/8

Showing 1-10 of 39 resultsSorted by cheapest first
1
2
3
4

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 12 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 12 August 2026.

The most flights from YTO to CHI are scheduled on a Tuesday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 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 £168 and £269 in September.
The cheapest return price found within the last 5 days was £148 on Air Canada (16 Sept–21 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 2h. United Airlines provides one of the quickest options available for as low as £156. Airlines will cover a distance of 436 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 £232 on average, our data indicates £272 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.