Using the online timetable is an easy way to look at all the direct flights Boston — Chicago
158 flights in a week
Departure and arrival times are local (Boston and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:00 | 06:55 | thu, fri, sun | WN699 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:15 | 07:00 | sat | WN699 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:20 | 07:10 | mon | WN699 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:30 | 07:20 | tue, wed | WN699 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 08:00 | daily | UA1414 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:30 | 08:41 | tue, wed | AA1328 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:30 | 08:20 | sat | WN833 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:52 | 09:03 | mon, thu, fri, sat, sun | AA1328 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:10 | mon, tue, wed, fri, sat, sun | B6311 | JetBlue | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:05 | 09:00 | sun | WN833 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:10 | mon, tue, wed, thu, fri | WN833 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:25 | mon, tue, wed, thu, fri | DL2570 | Delta Connection | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:15 | 09:24 | sat | DL5860 | Delta Connection | 3h 9m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:16 | 09:22 | mon, tue, wed, fri, sat, sun | UA2488 | United Express | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:25 | 09:35 | sun | DL2570 | Delta Connection | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:05 | wed | AA1022 | American Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:10 | daily | B6311 | JetBlue | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:15 | 10:20 | mon, thu, fri, sun | UA1349 | United Express | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:20 | 11:25 | tue, wed, sat | UA1349 | United Express | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:24 | 12:35 | mon, tue, wed, thu, sun | AA4358 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:48 | 12:59 | sat | AA4413 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:02 | 13:07 | mon, tue, wed, sat | UA503 | United Express | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:09 | 13:20 | mon, tue, wed | AA4413 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:25 | 13:15 | tue, wed | WN527 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 11:30 | 13:27 | wed | DL5606 | Delta Connection | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:40 | 13:30 | sun | WN527 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 11:50 | 13:40 | mon, thu, fri | WN527 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 12:09 | 14:15 | mon, tue, wed, thu, fri, sun | AA2489 | American Eagle | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:10 | 14:15 | mon, wed, thu, fri | UA1732 | United Express | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:10 | 14:16 | tue | UA1732 | United Express | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:20 | 14:25 | sun | UA1732 | United Express | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:35 | 14:20 | sat | WN527 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 13:45 | 15:30 | sun | WN3514 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:00 | 15:45 | tue, wed | WN3514 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:00 | 16:04 | fri | B6811 | JetBlue | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:40 | 16:30 | tue, wed | WN701 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 15:10 | 16:55 | mon, thu, fri | WN3514 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 15:20 | 17:24 | mon, thu, fri, sun | B6811 | JetBlue | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:51 | 18:07 | mon, tue, wed | AA4628 | American Eagle | 3h 16m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:19 | 18:35 | sun | AA4628 | American Eagle | 3h 16m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:25 | 18:31 | mon, tue, wed, thu, fri | DL2646 | Delta Connection | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:30 | 18:35 | daily | UA2040 | United Express | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:31 | 19:48 | mon, tue, wed, thu, fri, sun | AA1245 | American Eagle | 3h 17m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:45 | 19:35 | mon, tue, thu, sat | WN701 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:54 | 20:00 | sat | AA1245 | American Eagle | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:00 | 19:50 | tue, wed | WN1266 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 18:23 | 20:25 | thu | UA1015 | United Express | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:25 | 20:25 | mon, thu, fri | WN1266 | Southwest Airlines | 3h 0m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 18:28 | 20:30 | mon, thu, fri | UA1015 | United Express | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:32 | 20:30 | sun | UA1015 | United Express | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:35 | 20:30 | sat, sun | WN1266 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 18:45 | 21:01 | sat | AA3901 | American Eagle | 3h 16m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:05 | 20:55 | mon, fri | WN701 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:16 | 21:30 | mon, tue, wed, thu, fri, sun | AA1385 | American Eagle | 3h 14m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:20 | 22:16 | mon, sun | DL5858 | Delta Connection | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |