Statistics on Toronto-Chicago flights: what is the right price and when to buy your plane ticket?
Best time to go: what is the RIGHT price for a round-trip flight to Chicago (from: Toronto)
The average price to go to Chicago from Toronto airport is $ 382 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 347 (in february) and $ 435 (in november), which is a saving of $ 35 or a surplus of $ 54 (compared to the average price) depending on the period you leave.
The analysis of all the prices reveals that the most frequent price is between $222 to $277 and that it is generally more economical to leave on a wednesday and return on a tuesday on a direct flight.
Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to Chicago before booking your flight.
If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your Toronto-Chicago plane ticket.
How are these data calculated?
We have studied a sample of 60000 airfare prices from previous years for flights to Chicago from Toronto and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.
Average price depending on the departure month
Data analysis:
By leaving in february, the price of the plane ticket will statistically be the cheapest ($ 347, saving $ 35 compared to the average price over the year which is $ 382). Conversely, november will be the most expensive ($ 435).
Flight Toronto-Chicago: when is the best time to go for the best price?
| Month | Good price* | Average price | Our opinion |
|---|---|---|---|
| January | $ 318 | $ 364 | fair price |
| February | $ 283 | $ 347 the cheapest | very good price |
| March | $ 277 | $ 354 | fair price |
| April | $ 287 | $ 352 | good price |
| May | $ 303 | $ 387 | fair price |
| June | $ 301 | $ 381 | fair price |
| July | $ 325 | $ 405 | fair price |
| August | $ 318 | $ 404 | fair price |
| September | $ 313 | $ 383 | fair price |
| October | $ 320 | $ 381 | fair price |
| November | $ 320 | $ 435 the most expensive | very high price |
| December | $ 325 | $ 380 | fair price |
*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!
Price breakdown to travel from Toronto to Chicago
Data analysis:
The prices for flights from Toronto to Chicago range from $166 to $664. 7% of tickets were purchased at the minimum price (from $166 to $222), 1% at the maximum price (from $608 to $664). The majority of plane tickets were purchased in the range of $222 to $277 (18% of tickets).
Cheapest airlines for the Toronto->Chicago flight
There are 6 companies that serve Toronto from Chicago airport: Porter Airlines, Air Canada, United, WestJet, flair airlines and American Airlines.
Data analysis:
Of the 60000 flights analyzed in previous years, Porter Airlines was the airline that offered the best fare most often in the flight ticket search results (73% of the time) on the Toronto->Chicago route.
Which day of the week to leave?
Data analysis:
Statistically, Toronto-Chicago flights departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday as your departure date, you can save an average of $15. On the other hand, departing on a sunday may cost you an additional $20.
Which day of the week to come back?
Data analysis:
Statistically, return flights from Chicago to Toronto departing on a tuesday are cheaper than on other days of the week. By choosing a tuesday for your return date, you will save an average of $12. Conversely, departing from Chicago on a friday may cost you an additional $19.
Top prices Toronto-Chicago
| Round trip | Dates | Price | |
|---|---|---|---|
| Toronto → Chicago | 25-04 to 30-04-2025 | $ 175 | direct flight with Porter Airlines |
| Toronto → Chicago | 02-05 to 09-05-2025 | $ 170 | direct flight with Porter Airlines |
| Toronto → Chicago | 03-05 to 10-05-2025 | $ 176 | direct flight with Porter Airlines |
| Toronto → Chicago | 05-05 to 09-05-2025 | $ 177 | direct flight with Porter Airlines |
| Toronto → Chicago | 22-05 to 28-05-2025 | $ 173 | direct flight with Porter Airlines |
| Toronto → Chicago | 24-05 to 29-05-2025 | $ 176 | direct flight with Porter Airlines |
| Toronto → Chicago | 05-06 to 11-06-2025 | $ 172 | direct flight with Porter Airlines |
| Toronto → Chicago | 06-06 to 11-06-2025 | $ 172 | direct flight with Porter Airlines |
| Toronto → Chicago | 08-06 to 14-06-2025 | $ 170 | direct flight with Porter Airlines |
| Toronto → Chicago | 10-06 to 18-06-2025 | $ 173 | direct flight with Porter Airlines |
When to book your flight Toronto - Chicago to get the cheapest price?
Statistically, you will make the biggest savings by buying your plane ticket between 1 to 2 months in advance. However, you may end up paying a high price if you book between 11 to 12 months in advance.
Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a Toronto-Chicago flight, it is recommended to book your ticket on a wednesday.
How far in advance should I buy my flight?
Data analysis:
To get the cheapest flight ticket from Toronto to Chicago, it is recommended to buy it 1 to 2 months before departure (it is then on average 264 $, which is a saving of 118 $ compared to the overall average price). On the other hand, if you buy your ticket 11 to 12 months in advance, you will pay the full price (166 $ more than the average price).
Depending on the departure month
The best time to buy your Toronto to Chicago flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.
| Departure on... | How far in advance should I book? |
|---|---|
| January | Best time: 1 to 2 months before departure (average price: 258 $) Other interesting period(s): 0 to 1 month ($ 304), 2 to 3 months ($ 299) |
| February | Best time: 1 to 2 months before departure (average price: 244 $) Other interesting period(s): 0 to 1 month ($ 307), 2 to 3 months ($ 296) |
| March | Best time: 1 to 2 months before departure (average price: 220 $) Other interesting period(s): 0 to 1 month ($ 311), 2 to 3 months ($ 285), 3 to 4 months ($ 341) |
| April | Best time: 1 to 2 months before departure (average price: 215 $) Other interesting period(s): 0 to 1 month ($ 345), 2 to 3 months ($ 235), 3 to 4 months ($ 329) |
| May | Best time: 2 to 3 months before departure (average price: 245 $) Other interesting period(s): 1 to 2 months ($ 282), 3 to 4 months ($ 281) |
| June | Best time: 3 to 4 months before departure (average price: 272 $) Other interesting period(s): 0 to 1 month ($ 376), 1 to 2 months ($ 298), 2 to 3 months ($ 279), 4 to 5 months ($ 332) |
| July | Best time: 1 to 2 months before departure (average price: 296 $) Other interesting period(s): 0 to 1 month ($ 353), 2 to 3 months ($ 345), 3 to 4 months ($ 344), 4 to 5 months ($ 370) |
| August | Best time: 1 to 2 months before departure (average price: 267 $) Other interesting period(s): 0 to 1 month ($ 365), 2 to 3 months ($ 312), 3 to 4 months ($ 361), 4 to 5 months ($ 365), 5 to 6 months ($ 374) |
| September | Best time: 1 to 2 months before departure (average price: 272 $) Other interesting period(s): 0 to 1 month ($ 353), 2 to 3 months ($ 283), 3 to 4 months ($ 309), 4 to 5 months ($ 339) |
| October | Best time: 1 to 2 months before departure (average price: 282 $) Other interesting period(s): 0 to 1 month ($ 363), 2 to 3 months ($ 302), 3 to 4 months ($ 309), 4 to 5 months ($ 334), 5 to 6 months ($ 352) |
| November | Best time: 1 to 2 months before departure (average price: 270 $) Other interesting period(s): 0 to 1 month ($ 345), 2 to 3 months ($ 290), 3 to 4 months ($ 368), 6 to 7 months ($ 431) |
| December | Best time: 1 to 2 months before departure (average price: 256 $) Other interesting period(s): 0 to 1 month ($ 339), 2 to 3 months ($ 310), 3 to 4 months ($ 356) |
What day of the week should I book my flight ticket?
Data analysis:
Statistically, wednesday is the day when plane tickets for Toronto->Chicago are the cheapest. So, by buying your plane ticket on a wednesday, you will save $6. Conversely, by buying it on a saturday, you may end up paying $6 more.
Toronto to Chicago: flight price when booking today
Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.
| Month | Current price | Our opinion | |
|---|---|---|---|
| April 2025 | $ 283 $175 to $467 | very good price | Find a flight |
| May 2025 | $ 223 $170 to $450 | very good price | Find a flight |
| June 2025 | $ 217 $170 to $281 | very good price | Find a flight |
| July 2025 | $ 254 $210 to $368 | very good price | Find a flight |
| August 2025 | $ 255 $212 to $289 | very good price | Find a flight |
| September 2025 | $ 336 $233 to $458 | very good price | Find a flight |
| October 2025 | $ 452 $308 to $576 | high price | Find a flight |
| November 2025 | $ 424 $281 to $565 | very good price | Find a flight |
| December 2025 | $ 470 $361 to $564 | high price | Find a flight |
| January 2026 | $ 439 $439 to $439 | high price | Find a flight |
| February 2026 | $ 431 $407 to $451 | high price | Find a flight |
Data analysis:
Compared to the average price, april, may, june, july, august, september and november are cheaper to travel to Chicago. So it may be interesting to book now to leave during these months!