Using the online timetable is an easy way to look at all the direct flights Chicago — Boston
235 flights in a week
Departure and arrival times are local (Chicago and Boston)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:15 | 09:30 | mon, thu, fri | WN862 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 06:15 | 09:35 | mon, tue, wed, thu, fri | DL5636 | Delta Air Lines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:15 | 09:38 | thu, fri | DL5636 | Delta Air Lines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:20 | 09:35 | mon, thu, fri | WN5486 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 06:25 | 09:50 | mon, tue, thu, fri | DL5652 | Delta Air Lines | 2h 25m | O'Hare International Airport — Logan International Airport | Select dates |
| 06:25 | 09:47 | mon, tue, wed, thu | DL5652 | Delta Air Lines | 2h 22m | O'Hare International Airport — Logan International Airport | Select dates |
| 07:00 | 10:15 | sun | WN862 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 07:05 | 10:10 | WN862 | Southwest Airlines | 2h 5m | Chicago Midway International Airport — Logan International Airport | Select dates | |
| 07:05 | 10:34 | sun | AA4353 | American Airlines | 2h 29m | O'Hare International Airport — Logan International Airport | Select dates |
| 07:06 | 10:35 | thu | AA4353 | American Airlines | 2h 29m | O'Hare International Airport — Logan International Airport | Select dates |
| 07:10 | 10:29 | wed, sat, sun | UA1803 | United Airlines | 2h 19m | O'Hare International Airport — Logan International Airport | Select dates |
| 07:10 | 10:30 | mon, tue, wed, thu, fri, sun | UA1803 | United Airlines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 07:10 | 10:26 | mon, thu, sat, sun | UA1803 | United Airlines | 2h 16m | O'Hare International Airport — Logan International Airport | Select dates |
| 07:15 | 10:38 | tue, wed, thu, sun | UA1803 | United Airlines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 07:15 | 10:30 | tue, wed | WN862 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 07:37 | 10:58 | daily | UA1803 | United Airlines | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:00 | 11:24 | sat | DL5641 | Delta Air Lines | 2h 24m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:00 | 11:23 | sat | DL5636 | Delta Air Lines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:00 | 11:26 | sat | DL5636 | Delta Air Lines | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:15 | 11:49 | sat | AA4801 | American Airlines | 2h 34m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:15 | 11:30 | tue, wed | WN5486 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 08:20 | 11:38 | daily | AA2997 | American Airlines | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:35 | 11:50 | WN862 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates | |
| 08:35 | 11:58 | wed, thu, fri | AA4502 | American Airlines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:35 | 11:45 | sun | WN5486 | Southwest Airlines | 2h 10m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 08:38 | 12:07 | mon, tue, sun | B6312 | JetBlue Airways | 2h 29m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:40 | 12:00 | mon, fri | AA2997 | American Airlines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 08:50 | 12:14 | sun | DL5636 | Delta Air Lines | 2h 24m | O'Hare International Airport — Logan International Airport | Select dates |
| 09:00 | 12:26 | mon, tue, wed, thu, fri | DL1810 | Delta Air Lines | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 09:26 | 12:53 | sun | UA1888 | United Airlines | 2h 27m | O'Hare International Airport — Logan International Airport | Select dates |
| 09:50 | 13:08 | thu | DL644 | Delta Air Lines | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 09:56 | 13:16 | thu | UA1282 | United Airlines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 10:15 | 13:41 | sat | DL5595 | Delta Air Lines | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 10:20 | 13:47 | sun | AA4434 | American Airlines | 2h 27m | O'Hare International Airport — Logan International Airport | Select dates |
| 10:52 | 14:14 | fri, sun | UA2731 | United Airlines | 2h 22m | O'Hare International Airport — Logan International Airport | Select dates |
| 10:55 | 14:24 | fri, sun | B6312 | JetBlue Airways | 2h 29m | O'Hare International Airport — Logan International Airport | Select dates |
| 10:57 | 14:18 | mon, tue, fri, sat, sun | B6312 | JetBlue Airways | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 11:00 | 14:18 | tue, wed, thu, fri, sat | UA691 | United Airlines | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 11:27 | 14:48 | sat | B6312 | JetBlue Airways | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 11:32 | 14:53 | wed, thu | B6312 | JetBlue Airways | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:20 | 16:43 | mon, tue, wed, thu, fri, sun | DL5644 | Delta Air Lines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:20 | 16:40 | mon, tue, wed, thu | DL5644 | Delta Air Lines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:20 | 16:30 | sat | WN5487 | Southwest Airlines | 2h 10m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 13:30 | 16:46 | tue, wed, thu | AA2837 | American Airlines | 2h 16m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:34 | 16:47 | mon, fri, sat, sun | AA2877 | American Airlines | 2h 13m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:35 | 16:49 | mon, wed, thu, fri, sat, sun | AA1485 | American Airlines | 2h 14m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:37 | 16:45 | fri | AA2837 | American Airlines | 2h 8m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:40 | 16:55 | sat | AA3811 | American Airlines | 2h 15m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:43 | 16:54 | thu, fri, sun | AA2877 | American Airlines | 2h 11m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:46 | 17:08 | sat | AA3811 | American Airlines | 2h 22m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:56 | 17:14 | thu, fri | UA378 | United Airlines | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 13:59 | 17:19 | mon, tue, wed, thu, fri, sun | UA378 | United Airlines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 14:00 | 17:18 | tue, wed | UA378 | United Airlines | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 14:02 | 17:25 | fri | UA378 | United Airlines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 14:11 | 17:35 | sun | UA561 | United Airlines | 2h 24m | O'Hare International Airport — Logan International Airport | Select dates |
| 14:30 | 17:40 | tue, wed | WN5488 | Southwest Airlines | 2h 10m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 14:50 | 17:55 | sun | WN3122 | Southwest Airlines | 2h 5m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 15:34 | 18:51 | fri | AA1461 | American Airlines | 2h 17m | O'Hare International Airport — Logan International Airport | Select dates |
| 16:00 | 19:15 | fri | WN745 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 17:00 | 20:21 | tue, wed, thu, fri | DL5700 | Delta Air Lines | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 17:05 | 20:24 | mon, tue, fri | DL631 | Delta Air Lines | 2h 19m | O'Hare International Airport — Logan International Airport | Select dates |
| 17:05 | 20:25 | thu | UA3776 | United Airlines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 17:15 | 20:36 | sat | DL5644 | Delta Air Lines | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 17:45 | 21:09 | tue, wed, thu, fri | DL2327 | Delta Air Lines | 2h 24m | O'Hare International Airport — Logan International Airport | Select dates |
| 17:47 | 21:10 | fri | B61226 | JetBlue Airways | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 17:50 | 21:18 | sun | DL5647 | Delta Air Lines | 2h 28m | O'Hare International Airport — Logan International Airport | Select dates |
| 18:10 | 21:36 | tue, wed, thu, fri | B61226 | JetBlue Airways | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 18:17 | 21:38 | daily | UA1568 | United Airlines | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 18:18 | 21:01 | thu | WN9009 | Southwest Airlines | 1h 42m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 18:20 | 21:46 | mon, tue, wed, thu, fri | UA1568 | United Airlines | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 18:21 | 21:39 | fri | UA1568 | United Airlines | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 18:23 | 21:41 | mon | UA1568 | United Airlines | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 18:50 | 22:16 | tue, wed, thu, fri | AA1033 | American Airlines | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 18:55 | 22:21 | mon | B61226 | JetBlue Airways | 2h 26m | O'Hare International Airport — Logan International Airport | Select dates |
| 19:15 | 22:30 | tue, wed | WN2383 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 19:45 | 23:00 | fri | WN2383 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 19:50 | 23:08 | mon, tue, fri, sat, sun | B6412 | JetBlue Airways | 2h 18m | O'Hare International Airport — Logan International Airport | Select dates |
| 19:55 | 23:15 | daily | B6412 | JetBlue Airways | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 19:59 | 23:22 | mon, sun | DL5812 | Delta Air Lines | 2h 23m | O'Hare International Airport — Logan International Airport | Select dates |
| 19:59 | 23:19 | mon, thu, fri | DL5812 | Delta Air Lines | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 20:05 | 23:15 | sat, sun | WN5489 | Southwest Airlines | 2h 10m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 20:10 | 23:30 | tue, thu | B6412 | JetBlue Airways | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 20:10 | 23:20 | mon, thu, fri | WN5489 | Southwest Airlines | 2h 10m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 20:15 | 23:47 | tue, wed, fri, sun | DL2854 | Delta Air Lines | 2h 32m | O'Hare International Airport — Logan International Airport | Select dates |
| 20:18 | 23:38 | wed | B6412 | JetBlue Airways | 2h 20m | O'Hare International Airport — Logan International Airport | Select dates |
| 20:25 | 23:35 | sat, sun | WN5489 | Southwest Airlines | 2h 10m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 20:30 | 23:45 | sun | WN2383 | Southwest Airlines | 2h 15m | Chicago Midway International Airport — Logan International Airport | Select dates |
| 20:35 | 23:54 | daily | AA2682 | American Airlines | 2h 19m | O'Hare International Airport — Logan International Airport | Select dates |
| 21:10 | 00:31 | mon, tue, fri, sat | UA2627 | United Airlines | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |
| 21:28 | 00:45 | mon, tue | UA2627 | United Airlines | 2h 17m | O'Hare International Airport — Logan International Airport | Select dates |
| 21:30 | 00:51 | sun | UA2627 | United Airlines | 2h 21m | O'Hare International Airport — Logan International Airport | Select dates |