Using the online timetable is an easy way to look at all the direct flights Toronto — Chicago
144 flights in a week
Departure and arrival times are local (Toronto and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 00:15 | 00:38 | mon | 3S442 | AeroLogic | 1h 23m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:00 | 06:27 | sat | UA3917 | United Airlines | 1h 27m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:00 | 07:15 | daily | AA3524 | American Airlines | 2h 15m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:50 | 08:03 | wed, sun | UA5526 | United Airlines | 2h 13m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:50 | 07:55 | tue | UA333 | United Airlines | 2h 5m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:03 | 08:42 | mon | NetJets | 1h 39m | Pearson International Airport — Chicago Executive Airport | Select dates | |
| 08:15 | 09:13 | mon, thu, fri, sat, sun | AC8901 | Air Canada | 1h 58m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:00 | 10:05 | daily | UA1759 | United Airlines | 2h 5m | Pearson International Airport — O'Hare International Airport | Select dates |
| 09:15 | 10:05 | mon, tue, wed, thu, fri, sun | PD2387 | Porter Airlines Canada | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 09:15 | 10:05 | daily | PD2387 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 09:20 | 10:10 | tue, sat | PD2387 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 09:30 | 10:12 | fri | NetJets | 1h 42m | Pearson International Airport — Chicago Midway International Airport | Select dates | |
| 10:30 | 10:44 | sun | Turkish Airlines | 1h 14m | Pearson International Airport — O'Hare International Airport | Select dates | |
| 11:00 | 12:05 | thu, sun | UA3444 | United Airlines | 2h 5m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:00 | 11:50 | sat | PD2387 | Porter Airlines Canada | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 11:38 | 12:33 | daily | AA3604 | American Airlines | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:05 | 13:01 | daily | AC505 | Air Canada | 1h 56m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:12 | 14:09 | tue, wed, thu, fri, sat | AA3606 | American Airlines | 1h 57m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:14 | 14:11 | mon, fri, sun | AA3606 | American Airlines | 1h 57m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:14 | 14:14 | tue | AA3606 | American Airlines | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:30 | 14:25 | wed, sat | BR683 | EVA Air Cargo | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:15 | 15:10 | daily | AC507 | Air Canada | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:30 | 15:20 | mon, thu, fri, sun | PD2393 | Porter Airlines Canada | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 14:30 | 15:20 | mon, thu, fri, sun | PD2393 | Porter | 1h 50m | Toronto City Centre Airport — Chicago Midway International Airport | Select dates |
| 15:30 | 16:52 | mon, tue, wed, thu, fri, sun | UA3500 | United Airlines | 2h 22m | Pearson International Airport — O'Hare International Airport | Select dates |
| 15:30 | 16:40 | tue, sat, sun | UA3500 | United Airlines | 2h 10m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:30 | 17:12 | mon | NetJets | 1h 42m | Pearson International Airport — Chicago Midway International Airport | Select dates | |
| 16:40 | 17:40 | daily | AA3608 | American Airlines | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:50 | 17:48 | daily | AC8909 | Air Canada | 1h 58m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:30 | 18:50 | mon, wed, sun | UA4707 | United Airlines | 2h 20m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:15 | 18:50 | mon | 3S448 | AeroLogic | 1h 35m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:23 | 19:23 | daily | AA3610 | American Airlines | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:24 | 19:24 | mon, sun | AA3610 | American Airlines | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:40 | 19:40 | mon, fri, sat | AC509 | Air Canada | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:45 | 19:45 | mon, tue, wed, thu, fri, sun | AC509 | Air Canada | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 21:00 | 22:07 | mon, tue, wed, thu, fri, sun | UA5928 | United Airlines | 2h 7m | Pearson International Airport — O'Hare International Airport | Select dates |
| 21:00 | 22:05 | mon, tue, wed, thu, fri, sun | UA5829 | United Airlines | 2h 5m | Pearson International Airport — O'Hare International Airport | Select dates |
| 23:30 | 00:04 | wed | 3S442 | AeroLogic | 1h 34m | Pearson International Airport — O'Hare International Airport | Select dates |