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Cheap flights from Toronto to Chicago from £129

YTO — CHI
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Toronto to Chicago are usually found in February or March, booked 88 days in advance, depart on a Friday or Sunday 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

Wed 16/1208:05 -
Nonstop2h 03m
Wed 23/1220:50 -
Nonstop1h 42m
Deal found 1/11£207
Fri 11/1220:40 -
1 stop12h 05m
Sat 12/1211:05 -
Nonstop1h 58m
Deal found 1/11£212
Mon 7/1218:55 -
Nonstop2h 03m
Thu 10/1212:50 -
Nonstop1h 43m
Deal found 4/11£213
Mon 7/1212:05 -
Nonstop2h 15m
Thu 10/1207:20 -
Nonstop1h 47m
Deal found 4/11£221
Wed 25/1110:53 -
Nonstop2h 04m
Sun 29/1108:45 -
Nonstop1h 42m
Deal found 3/11£230
Mon 21/1219:26 -
Nonstop2h 14m
Sat 9/110:05 -
Nonstop1h 37m
Deal found 30/10£231
Fri 27/1117:55 -
Nonstop2h 10m
Mon 30/1120:40 -
Nonstop1h 43m
Deal found 4/11£236
Thu 3/1217:55 -
Nonstop2h 10m
Wed 9/1210:57 -
1 stop5h 52m
Deal found 3/11£238
Thu 3/1216:35 -
Nonstop2h 05m
Wed 9/1218:20 -
Nonstop1h 45m
Deal found 3/11£238
Wed 16/1216:35 -
Nonstop2h 05m
Wed 23/1218:20 -
Nonstop1h 45m
Deal found 1/11£239
Fri 25/1218:40 -
1 stop5h 59m
Sat 2/120:50 -
Nonstop1h 42m
Deal found 1/11£242
Thu 19/1106:00 -
1 stop5h 39m
Sun 22/1107:05 -
1 stop5h 25m
Deal found 1/11£243

Find flight deals from Toronto to Chicago

Round-trip from

£207

One-way from

£129

Popular in

October

Cheapest in

February

Average price

£215

Good round-trip deal

£170 or less

Good one-way deal

£147 or less
Air Canada
  • Air Canada
  • 16/12-23/12
  • Nonstop
  • 3h 45m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 22/11-31/12
  • Nonstop
  • 2h 13m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 2% potential increase in price (£3 potential increase over avg. return price).
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Cheapest flight prices on average. 0% potential price decrease (£2 potential savings vs. average return price).
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Average for round-trip flights in November 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

 
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 Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 9/1

06:10-09:53

1 stop4h 43m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£145

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 11/1

09:45-16:27

1 stop7h 42m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£145

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 23/4

12:15-18:40

1 stop7h 25m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£145

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 3/12

07:43-14:23

1 stop7h 40m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£148

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 28/11

12:15-18:30

1 stop7h 15m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£148

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 1/1

07:43-20:54

1 stop14h 11m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£150

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 27/11

10:00-17:00

1 stop8h 00m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£150

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 22/12

19:44-00:01

1 stop5h 17m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£150

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Mon 30/11

09:45-16:18

1 stop7h 33m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£150

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 20/12

19:44-00:01

1 stop5h 17m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£150

Flights are sorted by cheapest return flights first.

Deals found on 31/10

Showing 1-10 of 48 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

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 £193). Flying from Toronto to Chicago in October is currently the most expensive (average of £246). 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?

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 13% versus a flight in the afternoon.

Weekly flight availability from Toronto to Chicago

The most flights from YTO to CHI are scheduled on a Monday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (56 on average).

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

Airfare is typical for this route at the moment.
Toronto to Chicago flights typically cost between £170 and £265 in December.
The cheapest return price found within the last 5 days was £207 on Air Canada (16 Dec–23 Dec).

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 134 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 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 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.

Related info for your journey

  • How long is the flight from Toronto to Chicago?

    A quick flight from Toronto to Chicago can take about 2h 04m. Air Transat provides one of the quickest options available for as low as £247. 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 £148. Air Canada is 28% 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 Sun Country Air (100%), Royal Jordanian (91%) and Copa Airlines (88%).

  • What are the cheapest flights from Toronto to Chicago?

    Looking at all options, your cheapest flight can be booked for £155. While the most popular route (Toronto Island - Chicago O'Hare Intl) can be booked for £256 on average, our data indicates £408 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 £193). Flying from Toronto to Chicago in October is currently the most expensive (average of £246). 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

Alternative routes for Toronto to Chicago

Pearson Intl to O'Hare Intl flights

Top airline flying from Toronto to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest£148Average£170FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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