Using the online timetable is an easy way to look at all the direct flights Toronto — Chicago
183 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 Eagle | 2h 15m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:50 | 07:56 | mon, tue, wed, thu, fri, sat | UA490 | United Airlines | 2h 6m | Pearson International Airport — O'Hare International Airport | Select dates |
| 06:50 | 07:55 | sun | UA490 | 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 | 09:09 | daily | AC503 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:15 | 09:15 | tue, wed, thu | AC503 | Air Canada | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 08:15 | 09:13 | daily | 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 |
| 09:00 | 10:02 | daily | UA1538 | United Airlines | 2h 2m | 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 |
| 09:30 | 10:12 | fri | NetJets | 1h 42m | Pearson International Airport — Chicago Midway International Airport | Select dates | |
| 10:00 | 10:53 | daily | AC8903 | Air Canada | 1h 53m | Pearson International Airport — O'Hare 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 | daily | 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 |
| 11:32 | 12:27 | daily | AA3604 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:36 | 12:31 | mon, sun | AA3604 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 11:38 | 12:33 | sun | AA3604 | American Eagle | 1h 55m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:05 | 13:01 | mon, tue, wed, thu, fri, sun | AC505 | Air Canada | 1h 56m | Pearson International Airport — O'Hare International Airport | Select dates |
| 12:20 | 13:14 | daily | AC505 | Air Canada | 1h 54m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:10 | 14:10 | mon, tue, wed, thu, fri, sun | AA3606 | American Eagle | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:12 | 14:12 | sat | AA3606 | American Eagle | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:12 | 14:09 | sat | AA3606 | American Eagle | 1h 57m | Pearson International Airport — O'Hare International Airport | Select dates |
| 13:30 | 14:25 | wed, sat | BR683 | EVA Air | 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 | 15:25 | sat | BR683 | EVA Air | 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 |
| 14:45 | 15:35 | wed | BR683 | EVA Air | 1h 50m | Pearson International Airport — O'Hare International Airport | Select dates |
| 14:45 | 14:55 | sat | BR683 | EVA Air | 1h 10m | Pearson International Airport — O'Hare 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 | sat | 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 | sun | AA3608 | American Eagle | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 16:44 | 17:44 | daily | AA3608 | American Eagle | 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 | 18:39 | daily | UA1580 | United Airlines | 2h 9m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:30 | 18:52 | sat | UA5852 | United Airlines | 2h 22m | Pearson International Airport — O'Hare International Airport | Select dates |
| 17:30 | 18:50 | mon, sun | UA4707 | United Airlines | 2h 20m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:20 | 19:20 | mon, thu, fri, sun | AA3610 | American Eagle | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:23 | 19:23 | sun | AA3610 | American Eagle | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:24 | 19:24 | sun | AA3610 | American Eagle | 2h 0m | Pearson International Airport — O'Hare International Airport | Select dates |
| 18:45 | 19:45 | daily | 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 | wed | UA3512 | 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 |