Using the online timetable is an easy way to look at all the direct flights Boston — Chicago
113 flights in a week
Departure and arrival times are local (Boston and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:15 | 07:00 | mon, tue, thu, fri, sun | WN2012 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:20 | 07:10 | thu, fri, sun | WN699 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 05:30 | 07:20 | mon, tue, wed, thu, fri, sat | WN699 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 08:04 | mon, thu, sat, sun | UA1414 | United Express | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 06:10 | 08:20 | mon, wed, thu, sat | AA359 | American Airlines | 3h 10m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:05 | daily | AA1328 | American Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 07:30 | 09:41 | wed | DL5596 | Delta Air Lines | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:05 | wed | AA1022 | American Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:30 | 11:34 | mon, tue, wed, thu, fri, sun | UA1349 | United Express | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 09:51 | 12:05 | thu | AA4483 | American Airlines | 3h 14m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:00 | 22:46 | sat | UA3905 | United Express | 13h 46m | Logan International Airport — O'Hare International Airport | Select dates |
| 10:30 | 12:10 | sat | WN1482 | Southwest Airlines | 2h 40m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 10:30 | 12:34 | mon, tue, wed, thu, fri, sun | UA677 | United Express | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:45 | 14:49 | mon, wed, thu, fri, sat, sun | UA1732 | United Express | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:45 | 14:50 | tue, wed | UA1732 | United Express | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 12:55 | 15:06 | tue, wed | AA4074 | American Airlines | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 13:35 | 15:20 | wed, thu | WN2012 | Southwest Airlines | 2h 45m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:40 | 16:30 | mon, tue, wed, thu, fri | WN701 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 14:43 | 16:55 | tue, thu | AA3984 | American Airlines | 3h 12m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:20 | 17:25 | sun | B6811 | JetBlue | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:35 | 17:43 | mon, tue, wed, thu, fri, sat | B6811 | JetBlue | 3h 8m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:50 | 18:05 | tue | AA4157 | American Airlines | 3h 15m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:51 | 17:52 | wed | AA2700 | American Airlines | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 15:54 | 17:55 | thu, fri | AA2700 | American Airlines | 3h 1m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:10 | 18:19 | wed | DL5607 | Delta Air Lines | 3h 9m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:16 | 18:16 | mon, wed, thu, fri, sun | UA2040 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:20 | 18:42 | fri | AA4545 | American Airlines | 3h 22m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:49 | 18:49 | tue, sat | UA2040 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:50 | 18:55 | tue, wed | AA1542 | American Airlines | 3h 5m | Logan International Airport — O'Hare International Airport | Select dates |
| 16:55 | 18:45 | sat | WN701 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:42 | 20:00 | tue, wed | AA4545 | American Airlines | 3h 18m | Logan International Airport — O'Hare International Airport | Select dates |
| 17:45 | 19:35 | thu | WN701 | Southwest Airlines | 2h 50m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:55 | 19:50 | sun | WN701 | Southwest Airlines | 2h 55m | Logan International Airport — Chicago Midway International Airport | Select dates |
| 17:59 | 20:10 | mon, sun | AA1087 | American Airlines | 3h 11m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:21 | 20:25 | mon, sun | UA1015 | United Express | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:23 | 20:23 | wed | UA1015 | United Express | 3h 0m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:23 | 20:25 | mon, tue, thu, fri, sat, sun | UA1015 | United Express | 3h 2m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:29 | 20:35 | thu | UA1015 | United Express | 3h 6m | Logan International Airport — O'Hare International Airport | Select dates |
| 18:30 | 20:17 | mon | UA3903 | United Express | 2h 47m | Logan International Airport — O'Hare International Airport | Select dates |
| 19:14 | 21:20 | tue | AA379 | American Airlines | 3h 6m | 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 |
| 20:25 | 22:29 | mon, tue, wed, thu, fri | DL5858 | Delta Air Lines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |
| 20:40 | 22:44 | sun | DL5858 | Delta Air Lines | 3h 4m | Logan International Airport — O'Hare International Airport | Select dates |