Cheap flights from Toronto to Chicago

YTO — CHI
13 Dec — 20 Dec1
Return
1 adult
Economy
From?
To?
Tue 13/12
Tue 20/12

The best prices from Toronto to Chicago are usually found in June or November, booked 58 days in advance, depart on a Tuesday or Thursday and return on a Monday

How to find the cheapest flight from Toronto (YTO) to Chicago (CHI)

All the information you need to plan the best YTO to CHI flight in 2022: compare Toronto to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

YTO - CHI

Price

C$ 217 - C$ 300

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

Popular inDecemberHigh demand for flights, 12% potential price rise
Cheapest inJuneBest time to find cheap flights, 18% potential price drop
Round-trip fromC$ 296From Toronto (YTO) to Chicago (CHI)
One-way fromC$ 153One-way flight from Toronto (YTO) to Chicago (CHI)

What is the cheapest day to fly round-trip from Toronto to Chicago?

Monday is generally a great day to depart. Flying on this day could help you save up to 14%.

How far in advance should I book a flight from Toronto to Chicago?

Find a great deal and save up to 44% by booking at least 59 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Toronto to Chicago within the next two weeks, with the cheapest ticket starting at C$ 396.

What is the cheapest month to fly from Toronto to Chicago?

June is one of the best times of the year to fly to Chicago from Toronto. Prices for June average C$ 359 per person but you can even find prices for as low as C$ 221. The most expensive prices can be found in the month of December. Opting for a June flight can save you 14% on your journey compared to booking in December

When is the cheapest time to fly from Toronto to Chicago (YTO - CHI)?

Unlike in the evening, when flights are generally more expensive, you can save up to 17% on flights from Toronto to Chicago by exploring options for tickets in the afternoon.

Cheap flights from Toronto to Chicago in December, January 2022

The best prices found for YTO to CHI flights for December, January
20 Dec. - 4 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 246

Porter Airlines

Deal found 5/12

17 Jan. - 19 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 37m
C$ 247

Air Canada

Deal found 8/12

12 Jan. - 9 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 43m
C$ 251

Air Canada

Deal found 7/12

Toronto to Chicago 2022 flight deals

Cheap flights to Chicago from Toronto found for this year
20 Dec. - 4 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 246

Porter Airlines

Deal found 5/12

19 Dec. - 5 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 254

Porter Airlines

Deal found 5/12

20 Dec. - 3 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 257

Porter Airlines

Deal found 7/12

Cheap United Airlines flights from Toronto to Chicago

6 Jan. - 9 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

6h 01m
C$ 299

United Airlines

Deal found 8/12

17 Feb. - 20 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 12m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

11h 45m
C$ 302

United Airlines

Deal found 5/12

8 Jan. - 10 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

7h 23m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 35m
C$ 306

United Airlines

Deal found 8/12

  • One of the most popular airlines travelling from Toronto to Chicago is United Airlines. Flights on this route from United Airlines typically cost C$ 300.44 RT, a price that is 99% more expensive than the average Toronto to Chicago flight. The cheapest flight found was C$ 233 RT. Toronto Pearson Intl Airport is the most common Toronto airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Toronto to Chicago, United Airlines flights are 14% more popular than any other airline flying that same route.

Cheap American Airlines flights from Toronto to Chicago

11 Jan. - 5 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 08m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

14h 39m
C$ 313

American Airlines

Deal found 6/12

2 Feb. - 5 Feb.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 55m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

5h 05m
C$ 315

American Airlines

Deal found 5/12

26 Jan. - 4 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

1 stop

6h 01m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

4h 54m
C$ 330

American Airlines

Deal found 6/12

  • If you’re travelling from Toronto to Chicago, one of the more common airlines travelling that route is American Airlines. Flights from American Airlines travelling this route typically cost C$ 294.30 RT. This price is typically 106% cheaper than other airlines that offer Toronto to Chicago flights. When booking this route, the cheapest RT price found was C$ 212. Toronto Pearson Intl Airport is the most common Toronto airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Toronto to Chicago, American Airlines flights are 12% more popular than any other airline flying that same route.

Direct flights to Chicago from Toronto

Save time with Toronto to Chicago direct flight deals
20 Dec. - 4 Jan.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
MDW

Chicago Midway

YTZ

Toronto Island

Nonstop

1h 37m
C$ 246

Porter Airlines

Deal found 5/12

17 Jan. - 19 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 37m
C$ 247

Air Canada

Deal found 8/12

8 Mar. - 23 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 51m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 42m
C$ 251

Air Canada

Deal found 8/12

Last minute flights from Toronto to Chicago

Late deals on round-trip flights to Chicago from Toronto, departing today and this week
18 Dec. - 5 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 37m
C$ 283

Air Canada

Deal found 7/12

15 Dec. - 4 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

1 stop

10h 51m
C$ 313

United Airlines

Deal found 7/12

15 Dec. - 20 Dec.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

2h 11m
ORD

Chicago O'Hare Intl

YYZ

Toronto Pearson Intl

Nonstop

1h 37m
C$ 314

Air Canada

Deal found 5/12

One-way flights to Chicago from Toronto

The cheapest one-way flights from Toronto to Chicago
8 Mar.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 51m
C$ 153

Air Canada

Deal found 8/12

6 Jan.
YYZ

Toronto Pearson Intl

ORD

Chicago O'Hare Intl

Nonstop

1h 54m
C$ 154

Air Canada

Deal found 7/12

23 Mar.
YTZ

Toronto Island

MDW

Chicago Midway

Nonstop

1h 50m
C$ 156

Porter Airlines

Deal found 7/12

Related info for your journey

Useful info, stats and facts about Toronto to Chicago flights.

What airports serve Toronto to Chicago flights?

Flying out of Toronto to go to Chicago, you’ll show up to board your flight at Pearson International Airport in Toronto. Your flight will be heading for either Chicago O’Hare or Chicago Midway International Airport. You’ll find a variety of options for this route. You can fly direct, with one-stop, or more. There is a large range of prices for these flights. O’Hare International Airport is on the northwest side of the city in Chicago. It’s about 14 miles away from the city centre. The airport was built to take over for Midway originally. It’s a busy airport that is a hub for major airlines like United and American Airlines. Midway International Airport used to be the main airport in Chicago until O’Hare came along. This airport is still the second busiest one in the state of Illinois though. This is a major hub for Southwest Airlines.

Which airlines fly directly from Toronto to Chicago?

You can find a lot of direct flights from Toronto to Chicago. American Airlines has a few from Pearson to O’Hare. They’re about two hours long. Air Canada flies the same route. United also flies non-stop between Pearson and O’Hare.

What are the stopover options between Toronto to Chicago?

American Airlines has one-stop flights that land in Charlotte on the way to Chicago. This stopover varies in the time it adds to your travel day. You could be looking at six and a half hours, but also up to eleven hours. Delta makes a stopover in Detroit on the way to either Midway or O’Hare. These flights are only a few hours longer than the direct flights. Air Canada has a route that goes through Montreal before landing at O’Hare.

Do I need a passport or visa to fly from Toronto to Chicago?

While you do need your passport because you’re passing over the border into the US, you do not need a visa if you’re only going for a leisure trip. If you will be working or going to school, or investing on your trip, then you will need some kind of visa.

Which airlines flying from Toronto to Chicago have flexible cancellations due to COVID-19?

Air Canada, American Airlines, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Toronto to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Toronto to Chicago for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 246, but on average you can expect to pay C$ 258.

Are there direct flights from Toronto to Chicago for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Toronto to Chicago under C$ 300. A good price for a direct flight from Toronto to Chicago is less than C$ 263.

Are there last-minute flights available from Toronto to Chicago for under C$ 300?

There are currently 20+ open flights from Toronto to Chicago within the next 7 days for less than C$ 300.

What days are direct flights available from Toronto to Chicago?

You can find direct flights on the following days: Sunday, Monday, Friday, Saturday.

How many flights depart from Toronto to Chicago on average per day?

Per day, 8 flights depart from Toronto to Chicago on average.
Early Morning (Midnight to 6am) - 25% of flight departures
Morning (6am - Midday) - 63% of flight departures
Afternoon (Noon - 6pm) - 13% of flight departures

How long is the flight from Toronto to Chicago?

Airlines like Porter Airlines and Air Canada fly from Toronto to Chicago in about 1h 50m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 703 km. Most flights are nonstop.

What are the cheapest airlines flying from Toronto to Chicago round-trip?

Our cheapest airline available from Toronto to Chicago is Porter Airlines. Our recent data shows that you can find tickets from as low as C$ 246 on this airline. An additional option worth looking into is Air Canada, starting at C$ 247. Users have found that Porter Airlines is 31% cheaper than the other options available to this destination.

What are the most popular routes from Toronto to Chicago?

When deciding which route to take from Toronto to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago Midway or Toronto Pearson Intl - Chicago Midway as they are the most popular.

What are the most popular airlines that fly from Toronto to Chicago?

The most popular airlines flying from Toronto to Chicago are Undisclosed Carrier, American Airlines and Air Canada. Something to consider prior to booking your flight.

What are the most reliable airlines from Toronto to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Toronto to Chicago on time: Piedmont Airlines (100%), Finnair (100%), Republic Airways (95%).

What are the cheapest flights from Toronto to Chicago?

On average you can expect to pay C$ 1,933 for a flight from Toronto to Chicago. The cheapest flight overall is C$ 314 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 289.

Top 10 airlines flying from Toronto to Chicago

The chart below displays the airlines Cheapflights users travelling from Toronto to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapestC$ 27AverageC$ 42FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
WestJetCheapestC$ 131AverageC$ 417FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
DeltaCheapestC$ 169AverageC$ 308FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
SwoopCheapestC$ 174AverageC$ 189FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Swoop flights
Flair AirlinesCheapestC$ 181AverageC$ 243FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Flair Airlines flights
American AirlinesCheapestC$ 215AverageC$ 367FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Porter AirlinesCheapestC$ 229AverageC$ 314FlexibilityNo cancel feeOn-time52%COVID-19 safety
Search Porter Airlines flights
Air CanadaCheapestC$ 248AverageC$ 402FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
United AirlinesCheapestC$ 278AverageC$ 386FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
Air New ZealandCheapestC$ 289AverageC$ 402FlexibilityNo cancel feeOn-time78%COVID-19 safety
Search Air New Zealand flights

Hourly flight availability from Toronto to Chicago

See what time of day planes typically take off from Toronto to Chicago
18%of flight departuresEarly morningMidnight to 6 am
31%of flight departuresMorning6 am to noon
48%of flight departuresAfternoonNoon to 6 pm
3%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Toronto to Chicago

See how many times per day planes take to the skies headed from Toronto to Chicago
Sunday51daily flights
Monday59daily flights
Tuesday57daily flights
Wednesday59daily flights
Thursday57daily flights
Friday59daily flights
Saturday46daily flights