Using the online timetable is an easy way to look at all the direct flights Boston — Chicago
344 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 | wed, fri | AA3324 | American Eagle | 2h 51m | 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 |
| 05:15 | 06:45 | mon, thu, fri | WN2650 | Southwest Airlines | 2h 30m | Logan International Airport — Chicago Midway 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 | 07:05 | sun | WN2650 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:50 | 07:25 | sat | WN2650 | 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 |
| 06:00 | 07:56 | thu | AA3324 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:10 | 08:08 | sun | DL5719 | Delta Connection | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:10 | 08:05 | daily | UA1414 | United Airlines | 2h 55m | Logan International Airport — O'Hare 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 Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:56 | mon, wed, fri, sat | B6311 | JetBlue | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:04 | wed | AA1509 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:01 | 09:05 | mon, fri | AA1509 | American Eagle | 3h 4m | 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 |
| 07:20 | 09:15 | daily | DL2570 | Delta Connection | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:20 | 09:16 | mon, tue, wed, thu, fri | DL2570 | Delta Connection | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:25 | 09:15 | fri | DL2570 | Delta Connection | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:45 | 09:41 | mon, thu, fri | UA2251 | United Airlines | 2h 56m | 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 |
| 08:15 | 10:14 | tue, wed, thu, fri | AA1239 | American Eagle | 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 Eagle | 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 | 10:10 | thu, fri | WN1502 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway 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 | AA1239 | American Eagle | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:40 | 10:15 | mon | 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 |
| 09:03 | 10:54 | mon, tue, thu, fri, sat | UA600 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:10 | 10:50 | sat | WN1434 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:25 | 11:05 | tue, wed | WN1269 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 09:43 | 11:33 | mon, tue, wed, sun | UA365 | United Airlines | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:50 | 11:25 | sun | WN1434 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 10:30 | 11:41 | sat | JL15 | Jet Linx Aviation | 2h 11m | Pease Air Force Base — Chicago Executive Airport | Select dates |
| 10:40 | 12:31 | tue, sun | UA788 | United Airlines | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:00 | 12:50 | tue, wed | UA378 | United Airlines | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:00 | 13:00 | sat | AA1905 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:14 | 13:09 | mon, tue, wed, thu, fri, sun | AA3048 | American Eagle | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:28 | 13:24 | daily | AA1905 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:31 | 13:24 | mon, tue, wed, thu, fri, sun | DL2679 | Delta Connection | 2h 53m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:34 | 13:25 | sun | DL2679 | Delta Connection | 2h 51m | 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 Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:43 | 13:42 | mon | AA3287 | American Eagle | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 11:43 | 13:41 | thu, fri, sun | AA3287 | American Eagle | 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 |
| 12:00 | 13:49 | sat | UA3915 | United Airlines | 2h 49m | 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 |
| 12:15 | 13:50 | mon, thu, fri | WN1435 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 12:17 | 14:12 | sat | AA3672 | American Eagle | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:20 | 13:55 | sat | WN1435 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 12:26 | 14:24 | mon, tue, fri | AA547 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:26 | 14:22 | sun | AA547 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:30 | 14:20 | wed, thu, fri, sat | UA1732 | United Airlines | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:33 | 14:34 | wed, thu, sat | AA1457 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:35 | 14:31 | tue, wed | AA547 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:36 | 14:37 | sun | AA1457 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:40 | 14:41 | mon, fri | AA1457 | American Eagle | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:52 | 14:55 | tue, thu | AA1457 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:00 | 14:58 | sat | AA547 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:14 | 15:10 | mon, thu, fri | AA547 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:15 | 15:11 | sun | AA547 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:20 | 15:16 | sat | AA547 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:35 | 15:29 | fri | B6811 | JetBlue | 2h 54m | 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 |
| 13:40 | 15:32 | mon, 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 Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:56 | 15:54 | mon, tue, wed, thu, fri, sun | AA3711 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:56 | 16:00 | thu, sun | AA3711 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:03 | 16:00 | sat | AA3048 | American Eagle | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:10 | 16:08 | sun | AA3711 | American Eagle | 2h 58m | 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 |
| 14:35 | 16:10 | sun | WN1435 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:40 | 16:44 | wed, fri | AA3711 | American Eagle | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:43 | 16:39 | sun | B6811 | JetBlue | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:45 | 16:41 | sun | B6811 | JetBlue | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:45 | 16:49 | wed, thu, sat | AA3711 | American Eagle | 3h 4m | 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 |
| 14:55 | 16:50 | mon | DL2646 | Delta Connection | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 14:55 | 16:52 | wed | DL2646 | Delta Connection | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:00 | 17:03 | sat | AA3711 | American Eagle | 3h 3m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:15 | 16:50 | tue, wed, sat | WN2650 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 15:15 | 17:05 | daily | UA1989 | United Airlines | 2h 50m | Logan International Airport — O'Hare 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 | wed | UA1989 | United Airlines | 2h 47m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:46 | 17:45 | thu, fri, sun | AA1913 | American Eagle | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:59 | 17:54 | daily | AA1479 | American Eagle | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:00 | 17:55 | sat | AA1479 | American Eagle | 2h 55m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:04 | 17:54 | fri | B6811 | JetBlue | 2h 50m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:11 | mon, tue, wed, thu, fri, sun | DL2646 | Delta Connection | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:05 | 17:59 | thu | DL2646 | Delta Connection | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:20 | 18:24 | wed, sun | DL2646 | Delta Connection | 3h 4m | 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 |
| 16:27 | 18:21 | wed, thu, fri, sat | UA2040 | United Airlines | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:55 | 18:35 | sat | WN736 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway 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 | 19:33 | sat | AA4651 | American Eagle | 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 |
| 17:40 | 19:20 | tue, wed | WN1434 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:40 | 19:34 | daily | AA2837 | American Eagle | 2h 54m | Logan International Airport — O'Hare 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 |
| 17:55 | 19:35 | sun | WN187 | Southwest Airlines | 2h 40m | 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 Connection | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:16 | 20:10 | mon, tue | UA1015 | United Airlines | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:30 | 20:15 | mon, thu, fri | WN736 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway 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 Eagle | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:23 | 21:25 | sun | AA3233 | American Eagle | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:24 | 21:29 | tue, wed | AA4778 | American Eagle | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:24 | 21:21 | tue, wed | AA3233 | American Eagle | 2h 57m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:26 | 21:24 | sat | AA3233 | American Eagle | 2h 58m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:26 | 21:25 | mon, thu, fri | AA3233 | American Eagle | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:26 | 21:22 | mon, thu, fri | AA3233 | American Eagle | 2h 56m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:29 | 21:29 | sun | AA3233 | American Eagle | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:29 | 21:22 | fri | AA4470 | American Eagle | 2h 53m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:29 | 21:23 | tue, wed, sat | AA2837 | American Eagle | 2h 54m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:29 | 21:20 | thu | AA2837 | American Eagle | 2h 51m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:30 | 21:15 | thu | DL2676 | Delta Connection | 2h 45m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:45 | 21:25 | sun | WN117 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 19:55 | 21:54 | tue, thu | DL2676 | Delta Connection | 2h 59m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:55 | 21:56 | tue, wed | DL2676 | Delta Connection | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:59 | 22:00 | wed | DL2676 | Delta Connection | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:05 | 22:03 | mon, tue, wed, thu, fri, sun | DL2676 | Delta Connection | 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 |
| 20:20 | 21:55 | mon, thu, fri | WN1440 | Southwest Airlines | 2h 35m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 20:27 | 22:15 | thu | UA2229 | United Airlines | 2h 48m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:30 | 22:22 | sun | UA2229 | United Airlines | 2h 52m | Logan International Airport — O'Hare International Airport | Select dates |
| 21:46 | 23:34 | thu | UA3755 | United Airlines | 2h 48m | Logan International Airport — O'Hare International Airport | Select dates |