Using the online timetable is an easy way to look at all the direct flights Boston — Chicago
275 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 Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:00 | 06:51 | daily | AA3324 | American Eagle | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:00 | 06:40 | fri | WN1477 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:15 | 06:55 | mon, tue, wed, thu, fri | WN1477 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:20 | 07:00 | sat, sun | WN1477 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:24 | 07:25 | daily | AA3266 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:28 | 07:24 | daily | AA3324 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 05:30 | 07:15 | tue | WN1432 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:45 | 07:27 | wed | 5X9715 | UPS | 2h 42m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 06:00 | 07:56 | thu | AA3324 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:00 | 08:00 | tue | UA1414 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:00 | 08:01 | mon, sat | UA1414 | United Express | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:15 | 11:50 | wed | B61333 | JetBlue | 6h 35m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:30 | 06:47 | fri | 5X9853 | UPS | 1h 17m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:47 | 08:45 | tue, wed | AA1509 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:48 | 08:55 | tue | AA488 | American Eagle | 3h 7m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:57 | 08:55 | daily | AA1509 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:09 | 09:22 | daily | B6311 | JetBlue | 3h 13m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:20 | 09:22 | daily | DL2570 | Delta Connection | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:30 | 09:30 | sun | UA2467 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:44 | 09:54 | mon | AA4618 | American Eagle | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:50 | 09:50 | mon, thu | UA2467 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:55 | 09:53 | fri, sat | DL2570 | Delta Connection | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 09:55 | mon, thu, fri, sat, sun | UA366 | United Express | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:03 | tue, wed, thu, sat, sun | AA1239 | American Eagle | 3h 3m | 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 | 10:14 | sat | AA1239 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:15 | 10:14 | tue, wed, thu, fri | AA1239 | American Eagle | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:21 | 10:16 | tue, wed, thu | AA1239 | American Eagle | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:30 | 10:35 | mon, tue, wed, thu, sun | B6311 | JetBlue | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:35 | 10:30 | mon, wed, thu, sat | AA1239 | American Eagle | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:35 | 10:32 | mon, tue, wed, thu, fri, sat | AA1239 | American Eagle | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:54 | 10:59 | tue, wed | AA2312 | American Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:00 | 11:02 | sat | AA2312 | American Eagle | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:25 | 11:05 | tue, wed | WN1269 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:40 | 11:40 | daily | UA1349 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:53 | 11:43 | daily | UA378 | United Express | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:25 | 12:10 | mon, thu | WN1482 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 10:30 | 12:10 | sat | WN1482 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 10:40 | 12:31 | tue, sun | UA788 | United Express | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:40 | 12:40 | tue | UA1314 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:48 | 12:52 | mon | AA4413 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:55 | 12:58 | tue | AA3799 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:03 | 13:06 | thu | AA2312 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:05 | 13:08 | sun | AA2312 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:14 | 13:11 | daily | AA2312 | American Eagle | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:14 | 13:12 | mon | AA2312 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:45 | 13:40 | fri, sat | DL2679 | Delta Connection | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:56 | 14:02 | sun | AA1440 | American Eagle | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:17 | 14:15 | sat | AA1457 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:25 | 14:25 | mon, tue, wed, thu | UA1732 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:41 | 14:42 | tue, wed | AA1457 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:45 | 14:39 | mon, thu, fri, sun | DL2679 | Delta Connection | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:45 | 14:46 | fri | AA1457 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:51 | 14:52 | thu | AA1457 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:55 | 14:49 | mon, tue, wed, thu, sun | DL2679 | Delta Connection | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:05 | 14:45 | mon, thu | WN1484 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 13:35 | 15:20 | tue | WN2012 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 13:40 | 15:40 | daily | AA1859 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:42 | 15:46 | mon, tue | AA832 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:45 | 15:49 | daily | AA3711 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:50 | 15:30 | tue, wed | WN557 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:49 | 16:55 | tue | AA3691 | American Eagle | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:50 | 16:49 | sat | DL5722 | Delta Connection | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:10 | 17:10 | mon, tue, wed, thu, sun | UA1301 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:15 | 17:05 | daily | UA1989 | United Express | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:17 | 17:07 | wed, thu, fri, sat | UA1301 | United Express | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:18 | 17:05 | wed | UA1989 | United Express | 2h 47m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:20 | 17:10 | sat | UA1989 | United Express | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:51 | 17:52 | wed | AA2700 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:54 | 17:55 | thu, fri | AA2700 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:55 | 17:55 | tue, wed, thu | B6811 | JetBlue | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:02 | 18:24 | mon, tue | YX4392 | American Eagle | 3h 22m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:18 | fri | B6811 | JetBlue | 3h 13m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:10 | 18:10 | fri | DL2646 | Delta Connection | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:10 | 18:10 | tue, wed, thu, fri | UA2040 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:12 | 18:22 | mon | B6811 | JetBlue | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:15 | 18:10 | daily | UA2040 | United Express | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:30 | 17:39 | thu | YX5905 | Republic Airways | 2h 9m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:45 | 18:30 | sat | WN1779 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:05 | 18:50 | wed | WN1779 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:22 | 19:36 | mon, tue, wed, thu, sun | AA1443 | American Eagle | 3h 14m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:30 | 19:33 | sat | AA4651 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:44 | 19:45 | tue | AA3090 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:15 | 20:10 | mon, tue, thu, fri, sat, sun | UA1015 | United Express | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:23 | 20:23 | mon, tue, thu, sun | UA1015 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:25 | 20:25 | tue | UA1015 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:50 | 20:40 | mon, thu | WN1779 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:13 | 21:25 | sun | AA2504 | American Eagle | 3h 12m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:19 | 21:25 | tue | AA2504 | American Eagle | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:25 | 21:23 | mon, thu, fri, sun | AA2837 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:30 | 21:19 | tue, wed, thu, fri, sun | DL2676 | Delta Connection | 2h 49m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:45 | 21:34 | sun | DL2676 | Delta Connection | 2h 49m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:01 | 21:26 | fri | 5X9719 | UPS | 2h 25m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:30 | 22:30 | mon, thu, sun | UA2229 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:30 | 22:31 | sun | UA2229 | United Express | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:47 | 22:35 | mon, thu, fri, sun | UA2229 | United Express | 2h 48m | Logan International Airport — O'Hare International Airport | Select dates |
| 21:35 | 23:15 | mon, thu, fri | WN1488 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |