Using the online timetable is an easy way to look at all the direct flights Boston — Chicago
222 flights in a week
Departure and arrival times are local (Boston and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:00 | 06:58 | mon, tue, wed, thu, fri, sun | AA3324 | American Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:15 | 06:50 | thu, sat | WN1431 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:25 | 07:00 | tue, wed | WN1435 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:30 | 07:05 | sun | WN1431 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 07:55 | mon, tue, wed, thu, fri, sun | B6311 | JetBlue | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:07 | 08:05 | daily | UA1414 | United Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:10 | 08:08 | sun | DL5719 | Delta Air Lines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:40 | mon, thu, fri | WN1433 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 08:55 | sat | B6311 | JetBlue | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:05 | daily | AA1509 | American Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:20 | 09:18 | mon, tue, wed, thu, fri | DL2570 | Delta Air Lines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:20 | 09:00 | tue | WN1431 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 07:40 | 09:36 | sat | UA1857 | United Airlines | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:44 | 09:39 | sat | UA1909 | United Airlines | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:45 | 09:43 | mon, fri, sun | UA1909 | United Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:05 | 10:01 | thu | AA1239 | American Airlines | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:15 | 10:14 | wed, thu | AA1239 | American Airlines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:15 | 09:48 | sat | 5X2019 | UPS | 2h 33m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 08:21 | 10:16 | tue, wed, thu | AA1239 | American Airlines | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:24 | 09:57 | sat | 5X2019 | UPS | 2h 33m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 08:30 | 10:05 | sun | WN1435 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 08:35 | 10:27 | sat | DL2570 | Delta Air Lines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:40 | 10:15 | mon, thu, fri | WN1435 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 08:50 | 10:25 | sat | WN1435 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:00 | 10:35 | tue, wed | WN1375 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:03 | 10:54 | mon, thu, fri, sat | UA546 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:40 | 12:31 | sun | UA1298 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:31 | 13:24 | mon, tue, wed, thu, fri, sun | DL2679 | Delta Air Lines | 2h 53m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:35 | 13:10 | fri | WN1100 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 11:41 | 13:39 | tue, wed | AA3287 | American Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:43 | 13:42 | mon | AA3287 | American Airlines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:43 | 13:41 | thu, fri, sun | AA3287 | American Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:52 | 13:43 | sat | UA1732 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:00 | 13:51 | tue, wed, thu, fri | UA1732 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:02 | 13:53 | mon | UA1732 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:15 | 14:03 | sun | UA1732 | United Airlines | 2h 48m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:17 | 14:12 | sat | AA3672 | American Airlines | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:26 | 14:24 | mon, tue, wed, thu, fri | AA547 | American Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:26 | 14:22 | sun | AA547 | American Airlines | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:02 | 15:01 | mon, tue, wed, thu, fri, sun | AA3309 | American Airlines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:40 | 15:40 | daily | AA1859 | American Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:40 | 15:32 | thu, fri | B6811 | JetBlue | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:45 | 15:25 | sun | WN3911 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 13:47 | 15:43 | daily | AA2976 | American Airlines | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:50 | 15:30 | tue, wed | WN1433 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 13:57 | 15:56 | mon, thu, fri, sat | AA3309 | American Airlines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:58 | 15:57 | tue | AA3309 | American Airlines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:59 | 15:53 | mon, fri | B6811 | JetBlue | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:05 | 16:03 | fri | AA3711 | American Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:08 | 16:03 | mon, tue, wed, fri | AA3309 | American Airlines | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:30 | 16:05 | mon, thu, fri | WN1437 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:50 | 16:49 | sat | DL5722 | Delta Air Lines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:05 | 17:10 | tue, wed, fri | AA3711 | American Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:15 | 16:50 | sat | WN2511 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 15:16 | 17:05 | mon, tue, wed, thu, fri, sun | UA1032 | United Airlines | 2h 49m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:18 | 17:05 | sat | UA1032 | United Airlines | 2h 47m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:35 | 17:35 | sun | B6811 | JetBlue | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:51 | 17:53 | mon, thu, fri | AA2320 | American Airlines | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:11 | mon, tue, wed, thu, fri, sun | DL2646 | Delta Air Lines | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:27 | 18:20 | daily | UA2040 | United Airlines | 2h 53m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:30 | 18:36 | tue, thu, fri, sun | B6811 | JetBlue | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:15 | 18:55 | sun | WN2190 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:20 | 19:10 | tue, wed | WN1908 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:29 | 19:30 | mon, tue, wed, thu, fri, sun | AA2837 | American Airlines | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:30 | 19:35 | tue, sat | AA3711 | American Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:30 | 19:33 | sat | AA4651 | American Airlines | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:40 | 19:35 | sun | WN1096 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:50 | 19:40 | mon, thu, fri | WN784 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 18:03 | 20:00 | daily | UA1015 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:10 | 20:20 | sat | DL2646 | Delta Air Lines | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:50 | 20:35 | tue, wed | WN784 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:05 | 20:50 | sat | WN1096 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:14 | 21:20 | tue, wed | AA4778 | American Airlines | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:23 | 21:25 | sun | AA3233 | American Airlines | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:24 | 21:29 | tue, wed | AA4778 | American Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:26 | 21:24 | sat | AA3233 | American Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:26 | 21:25 | mon, thu, fri | AA3233 | American Airlines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:35 | 21:20 | sun | WN1908 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:05 | 22:03 | mon, tue, wed, thu, fri, sun | DL2676 | Delta Air Lines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:20 | 22:12 | mon, thu, fri | UA2229 | United Airlines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:25 | 22:28 | mon, wed, thu, fri | AA4117 | American Airlines | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:25 | 22:10 | mon, thu, fri | WN1908 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:30 | 22:22 | sun | UA2229 | United Airlines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |