Using the online timetable is an easy way to look at all the direct flights Boston — Chicago
368 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 | fri | AA1509 | American Eagle | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:06 | 07:06 | wed | AA4131 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:15 | 07:17 | daily | AA3452 | American Eagle | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:15 | 07:15 | daily | AA4131 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:15 | 06:50 | thu, fri | WN1431 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:45 | 07:20 | mon, thu, fri | WN576 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:50 | 07:30 | tue, wed | WN3726 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 08:04 | tue, wed, fri, sat | UA1414 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:00 | 07:57 | daily | UA1414 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:00 | 08:00 | mon, tue, thu, fri, sun | B6311 | JetBlue | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:00 | 07:58 | tue, thu, fri, sat, sun | UA1414 | United Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:10 | 08:05 | sat | WN787 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:10 | 08:18 | sun | AA1509 | American Eagle | 3h 8m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:20 | 08:00 | sat | WN576 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 08:15 | mon, thu, fri, sat | WN1159 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:35 | 08:31 | daily | AA1509 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:50 | 08:45 | thu, fri, sun | WN787 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:59 | 09:02 | mon, tue, wed, thu, fri, sun | AA1509 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:59 | 09:04 | fri | AA1509 | American Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:55 | mon | WN787 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 09:10 | tue | AA1509 | American Eagle | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:40 | thu | WN1433 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:09 | daily | DL2570 | Delta Connection | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:20 | 09:24 | wed | UA1316 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:25 | 09:29 | tue, thu | UA1316 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:30 | 09:34 | mon, fri, sat, sun | UA1316 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:40 | 09:15 | sun | WN576 | Southwest Airlines | 2h 35m | 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 |
| 07:45 | 09:42 | mon | UA278 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:45 | 09:43 | mon, thu, fri, sun | UA1857 | United Airlines | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:07 | sat | AA1509 | American Eagle | 3h 7m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:08 | sat | B6311 | JetBlue | 3h 8m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:02 | wed | B6311 | JetBlue | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:05 | 10:01 | thu | AA1239 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:10 | 10:05 | tue, wed | WN787 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 08:45 | 10:50 | thu, fri, sat, sun | AA2158 | American Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:45 | 10:49 | mon, tue, wed, thu, fri, sun | AA1741 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:45 | 10:24 | sat | 5X2019 | UPS | 2h 39m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 08:45 | 10:25 | sat | 5X2019 | UPS | 2h 40m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 08:45 | 10:09 | sat | 5X2019 | UPS | 2h 24m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 08:45 | 10:18 | sat | 5X2019 | UPS | 2h 33m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 08:55 | 10:57 | sat | UA316 | United Airlines | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:00 | 11:01 | daily | AA3939 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:00 | 10:35 | sat | WN2320 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:20 | 11:22 | mon, tue, wed, thu, fri, sun | UA316 | United Airlines | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:35 | 11:10 | mon, thu, fri | WN2320 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:35 | 11:26 | mon, thu, fri, sat, sun | UA378 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:38 | 11:36 | mon, tue, wed, thu, fri, sun | AA3776 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:54 | 11:51 | mon, tue, wed, thu, fri, sun | UA378 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:58 | 11:55 | sat | UA378 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:45 | 12:42 | mon, wed, sun | UA1485 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:00 | 13:00 | mon, wed, thu, fri, sun | AA4486 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:02 | 12:53 | mon, tue, wed, thu, fri | UA345 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:19 | 13:19 | mon, tue, wed, fri, sun | AA4486 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:25 | 13:14 | mon, wed, thu, sun | DL2679 | Delta Connection | 2h 49m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:35 | 13:25 | mon, thu, fri | WN2663 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 12:00 | 13:57 | thu | UA1732 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:05 | 13:55 | thu, fri, sun | WN3249 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 12:15 | 14:12 | daily | UA1732 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:30 | 14:15 | tue, wed | WN1159 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 12:30 | 14:25 | tue, wed | DL2679 | Delta Connection | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:30 | 14:21 | thu, fri | UA1732 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:40 | 14:15 | sun | WN277 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 12:55 | 14:40 | sun | WN1159 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 13:02 | 15:01 | mon, tue, wed, thu, fri, sun | AA3309 | American Eagle | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:40 | 15:40 | daily | AA1859 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:47 | 15:43 | daily | AA2976 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:49 | 15:50 | mon, thu, fri, sun | AA3632 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:50 | 15:51 | mon, wed, thu, fri, sun | AA3632 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:05 | 15:40 | tue, wed | WN576 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway 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 |
| 14:52 | 16:52 | daily | AA514 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:55 | 16:40 | fri | WN3249 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 15:05 | 17:02 | daily | UA1504 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:15 | 16:55 | sat | WN277 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 15:16 | 17:05 | sun | UA1504 | United Airlines | 2h 49m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:18 | 17:10 | tue | UA1504 | United Airlines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:20 | 17:19 | mon, tue, wed, thu, fri | DL2646 | Delta Connection | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:25 | 17:22 | thu, fri | DL2646 | Delta Connection | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:30 | 17:26 | mon, wed, thu, fri | DL2646 | Delta Connection | 2h 56m | 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 |
| 15:50 | 17:49 | sun | DL5595 | Delta Connection | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:51 | 17:53 | mon, thu, fri | AA2320 | American Eagle | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:52 | 17:54 | sat | AA4442 | American Eagle | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:55 | 17:55 | sun | DL5595 | Delta Connection | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:30 | 18:32 | mon, tue, wed, thu, fri, sat | UA2040 | United Airlines | 3h 2m | 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 |
| 16:37 | 18:28 | sun | UA2040 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:40 | 18:20 | mon, thu, fri | WN3726 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 16:45 | 18:42 | daily | UA2040 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:45 | 18:38 | tue | UA2040 | United Airlines | 2h 53m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:45 | 18:41 | daily | UA445 | United Airlines | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:47 | 18:40 | sat | UA2040 | United Airlines | 2h 53m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:10 | 19:14 | tue | DL2646 | Delta Connection | 3h 4m | 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 |
| 17:30 | 19:34 | mon, thu, fri | AA4434 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:30 | 19:35 | tue, sat | AA3711 | American Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:35 | 19:15 | tue, wed | WN1371 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:38 | 19:36 | daily | AA2837 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:38 | 19:41 | mon | AA2837 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:40 | 19:30 | tue, wed | WN855 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:45 | 19:50 | mon, tue, wed, thu, sun | AA4662 | American Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:45 | 19:25 | sat | WN3726 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:50 | 19:40 | thu | WN784 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 18:03 | 20:00 | wed, thu | UA1015 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:20 | 20:25 | fri | UA1015 | United Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:25 | 20:22 | mon, thu, sun | UA1015 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:25 | 20:10 | sun | WN4396 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 18:28 | 20:25 | mon, thu, fri, sun | UA1015 | United Airlines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:45 | 20:47 | sat | DL2646 | Delta Connection | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:23 | 21:25 | tue, wed, thu, sun | AA1691 | American Eagle | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:25 | 21:27 | sat | AA1691 | American Eagle | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:30 | 21:24 | thu | AA3233 | American Eagle | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:45 | 21:35 | mon, thu, fri, sun | WN1549 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:50 | 21:40 | sun | WN2330 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:55 | 21:51 | sun | DL2676 | Delta Connection | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:00 | 21:45 | mon, thu, sun | WN4580 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:10 | 21:55 | mon, tue | WN4580 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:10 | 22:06 | fri | DL2676 | Delta Connection | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:18 | 22:10 | sun | UA2229 | United Airlines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:20 | 22:00 | sun | WN4396 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:20 | 22:14 | tue, wed, thu, sun | DL2676 | Delta Connection | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:20 | 22:12 | thu | UA2229 | United Airlines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:25 | 22:28 | mon, wed, thu, fri | AA4117 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:25 | 22:10 | thu | WN1908 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:30 | 22:27 | fri | DL2676 | Delta Connection | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:32 | 22:24 | sun | UA3756 | United Airlines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:51 | 22:52 | tue, wed, thu, sat, sun | AA3010 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:59 | 22:56 | tue | DL2676 | Delta Connection | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |