Using the online timetable is an easy way to look at all the direct flights Boston — Chicago
296 flights in a week
Departure and arrival times are local (Boston and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 04:45 | 06:28 | sat | 5X9715 | UPS | 2h 43m | Logan International Airport — O'Hare International Airport | Select dates |
| 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 |
| 05:15 | 07:00 | thu, fri, sun | WN2012 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:20 | 07:05 | sat | WN1430 | Southwest Airlines | 2h 45m | 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 | mon, wed, thu | WN1432 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway 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 | wed | UA1414 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:00 | 08:17 | sat | AA1328 | American Eagle | 3h 17m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:01 | 08:05 | daily | UA1414 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:36 | 08:47 | fri | AA1328 | American Eagle | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:32 | tue | AA4618 | American Eagle | 3h 32m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:25 | 09:25 | fri | UA2467 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:30 | 09:30 | sun | UA2467 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:30 | 09:33 | mon, tue, wed, thu, fri | DL2570 | Delta Air Lines | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:44 | 09:54 | thu, sat, sun | AA4618 | American Eagle | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:45 | 09:45 | thu | UA2467 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:45 | 09:49 | thu, fri, sat | UA270 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:50 | 09:50 | mon, thu, sat | UA2467 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:59 | 10:23 | wed | AA4404 | American Eagle | 3h 24m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:30 | 10:35 | daily | B6311 | JetBlue | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:30 | 10:13 | tue, wed, thu | 5X2019 | UPS | 2h 43m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 09:25 | 11:15 | fri, sun | WN3724 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:30 | 11:34 | thu, fri, sat, sun | UA1349 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:30 | 11:35 | daily | DL5593 | Delta Air Lines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:40 | 11:40 | daily | UA1349 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:59 | 12:03 | mon, thu, fri, sun | AA3799 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:02 | 12:05 | thu, sun | AA3477 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:04 | 12:08 | mon, thu, fri, sun | AA3799 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:06 | 12:09 | mon, thu, fri, sun | AA3477 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:25 | 12:10 | sat | WN3771 | 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 | 12:40 | mon, sun | UA1314 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:44 | 12:54 | sun | AA4413 | American Eagle | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:45 | 12:55 | mon, sun | AA4413 | American Eagle | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:48 | 12:52 | thu, fri | AA4413 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:55 | 12:58 | tue, wed | AA3799 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:20 | 14:23 | sat | UA1732 | United Airlines | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:25 | 14:25 | mon, tue, wed, fri, sat, sun | UA1732 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:50 | 14:51 | sat | UA1732 | United Airlines | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:50 | 14:50 | tue, wed, thu, fri | UA1732 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:50 | 14:47 | daily | DL2679 | Delta Air Lines | 2h 57m | 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 | mon, tue, wed, thu, fri | 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, wed, sun | AA832 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:45 | 15:55 | mon, tue, wed, thu, fri, sun | AA488 | American Eagle | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:45 | 15:30 | fri, sun | WN1432 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 13:45 | 15:49 | mon, thu, fri, sat, sun | AA913 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:35 | 16:15 | sat | WN1081 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:44 | 16:59 | mon, tue, wed, sat, sun | AA3691 | American Eagle | 3h 15m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:50 | 16:49 | sat | DL5722 | Delta Air Lines | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:50 | 16:56 | mon, tue, sat, sun | DL5591 | Delta Air Lines | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:10 | 17:10 | mon, tue, wed, thu, sun | UA1301 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:17 | 17:07 | wed, thu, fri, sat | UA1301 | United Airlines | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:34 | 17:51 | sun | AA4649 | American Eagle | 3h 17m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:45 | 17:30 | sat | WN4496 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway 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 |
| 16:05 | 18:13 | mon, tue, wed, thu, fri, sun | DL2646 | Delta Air Lines | 3h 8m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:11 | mon, tue, wed, thu, sat | DL2646 | Delta Air Lines | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:08 | sat | DL2646 | Delta Air Lines | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:26 | daily | AA4392 | American Eagle | 3h 21m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:02 | mon | DL2646 | Delta Air Lines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:10 | 18:07 | sat | DL2646 | Delta Air Lines | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:15 | 18:19 | daily | UA2040 | United Airlines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:20 | 18:20 | mon, tue, wed | UA2040 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:30 | 18:57 | thu | AA4404 | American Eagle | 3h 27m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:31 | 18:46 | mon, tue, wed, thu, fri, sun | B6811 | JetBlue | 3h 15m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:36 | 19:03 | mon, tue, fri, sun | AA4404 | American Eagle | 3h 27m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:45 | 18:30 | sat | WN1030 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 16:50 | 18:35 | sun | WN3969 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:00 | 19:20 | sat | B6811 | JetBlue | 3h 20m | Logan International Airport — O'Hare 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 | 19:39 | tue | AA4385 | American Eagle | 3h 17m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:29 | 19:43 | mon, sun | B6811 | JetBlue | 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 |
| 17:30 | 19:43 | tue | AA4683 | American Eagle | 3h 13m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:23 | 20:23 | daily | UA1015 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:23 | 20:25 | thu, sat | UA1015 | United Airlines | 3h 2m | 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 |
| 18:50 | 20:45 | fri | WN1436 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 18:51 | 21:04 | fri | AA1121 | American Eagle | 3h 13m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:55 | 20:45 | thu, fri, sun | WN1030 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:01 | 21:14 | mon, wed, thu, fri | AA2500 | American Eagle | 3h 13m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:05 | 21:19 | sat | AA1562 | American Eagle | 3h 14m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:07 | 21:25 | sun | AA2500 | American Eagle | 3h 18m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:14 | 21:20 | tue | AA379 | American Eagle | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:40 | 21:40 | mon, tue, sun | DL5596 | Delta Air Lines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:45 | 21:45 | sat | DL5596 | Delta Air Lines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:50 | 21:50 | fri | DL5757 | Delta Air Lines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:52 | 21:47 | mon, tue, wed, thu, fri, sun | DL2676 | Delta Air Lines | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:55 | 21:40 | sat | WN3725 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:01 | 21:26 | fri | 5X9719 | UPS | 2h 25m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:15 | 21:58 | sun | 5X9715 | UPS | 2h 43m | Logan International Airport — Chicago Rockford International Airport | Select dates |
| 20:30 | 22:30 | mon, thu, fri, sun | UA2229 | United Airlines | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:30 | 22:31 | fri, sun | UA2229 | United Airlines | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:39 | 22:55 | fri | AA3185 | American Eagle | 3h 16m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:47 | 22:35 | mon, thu, fri, sun | UA2229 | United Airlines | 2h 48m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:50 | 22:35 | sun | WN1030 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 21:35 | 23:15 | thu | WN1488 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |