Using the online timetable is an easy way to look at all the direct flights Orlando — Chicago
221 flights in a week
Departure and arrival times are local (Orlando and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:20 | 08:05 | mon, thu, fri | WN1053 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 08:22 | fri, sun | F93853 | Frontier (Klondike the Polar Bear) | 2h 52m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:50 | 08:35 | sun | WN147 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:56 | 09:00 | wed | AA938 | American Eagle | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:05 | daily | AA938 | American Eagle | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:10 | thu, sat | AA938 | American Eagle | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:03 | mon, fri | AA938 | American Eagle | 3h 3m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:10 | 08:55 | tue, wed | WN3591 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:00 | sat | WN147 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:30 | 09:36 | mon, thu, fri, sat, sun | UA1097 | United Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:35 | 09:20 | thu, fri | WN1570 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:55 | 09:45 | thu | WN1719 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 09:54 | sat | F93853 | Frontier (Klondike the Polar Bear) | 2h 54m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:05 | 09:55 | sun | WN1719 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:05 | 09:47 | mon, fri | G41242 | Allegiant Air | 2h 42m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 08:35 | 10:17 | wed | G41250 | Allegiant Air | 2h 42m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 08:45 | 10:45 | sat | WN350 | Southwest Airlines | 3h 0m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:46 | 10:45 | mon, thu, sat | AA2279 | American Eagle | 2h 59m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:55 | 10:55 | tue, wed | AA1842 | American Eagle | 3h 0m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:00 | 10:46 | mon, fri | G41328 | Allegiant Air | 2h 46m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 09:15 | 11:00 | sat | WN3255 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:15 | 10:57 | wed | G41250 | Allegiant Air | 2h 42m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 09:20 | 11:05 | mon, thu, fri | WN3255 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:35 | 11:41 | daily | UA2341 | United Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:50 | 11:50 | mon | WN2956 | Southwest Airlines | 3h 0m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:00 | 11:46 | mon, fri | G41337 | Allegiant Air | 2h 46m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 10:05 | 11:50 | tue, wed, sun | WN1373 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:30 | 12:15 | thu, fri | WN3591 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:53 | 12:59 | sat | UA2207 | United Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:00 | 13:07 | mon, tue, wed, thu, fri, sun | UA2207 | United Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:00 | 13:05 | sun | WN2956 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:00 | 13:06 | sat, sun | UA2207 | United Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:25 | 13:05 | sun | WN3870 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:30 | 13:29 | mon, tue, wed, thu, fri, sun | AA1629 | American Eagle | 2h 59m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:45 | 13:25 | tue, wed | WN2409 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:10 | 13:50 | sat | WN1373 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:16 | 14:23 | daily | UA2475 | United Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:16 | 14:22 | wed, fri, sat | UA2475 | United Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:20 | 14:05 | mon, thu, fri | WN1373 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:24 | 14:10 | mon | G41277 | Allegiant Air | 2h 46m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 13:02 | 15:17 | sat | F93043 | Frontier (Klondike the Polar Bear) | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 13:05 | 14:55 | sat | WN1164 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:10 | 15:06 | mon, fri, sun | F93853 | Frontier (Klondike the Polar Bear) | 2h 56m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:20 | 15:20 | sat | WN3603 | Southwest Airlines | 3h 0m | Orlando International Airport — O'Hare International Airport | Select dates |
| 13:33 | 15:29 | mon | F93853 | Frontier (Klondike the Polar Bear) | 2h 56m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:00 | 15:50 | tue, wed | WN3643 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:00 | 16:14 | sat | AA1163 | American Eagle | 3h 14m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:07 | 16:10 | daily | NK2410 | Spirit Airlines | 3h 3m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:07 | 16:12 | sun | NK2410 | Spirit Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:30 | 16:37 | mon, thu, fri, sat, sun | UA1403 | United Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:30 | 16:36 | mon, tue, wed, thu, fri, sun | UA1403 | United Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:50 | 16:57 | daily | AA3031 | American Eagle | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:55 | 16:45 | sun | WN1788 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:00 | 16:45 | tue, wed | WN1500 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:08 | 16:51 | mon, fri | G42971 | Allegiant Air | 2h 43m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 15:30 | 17:25 | mon, thu, fri | WN1788 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:35 | 17:20 | sat | WN1186 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:36 | 17:44 | sun | AA2142 | American Eagle | 3h 8m | Orlando International Airport — O'Hare International Airport | Select dates |
| 15:50 | 17:55 | mon, tue, wed, thu, fri, sun | WN3603 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 15:55 | 17:50 | sat | WN1788 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:11 | 18:25 | daily | UA1828 | United Airlines | 3h 14m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:11 | 18:28 | wed, sun | UA1828 | United Airlines | 3h 17m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:15 | 18:10 | tue, wed | WN3255 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:18 | 18:41 | mon, sat, sun | F93043 | Frontier (Klondike the Polar Bear) | 3h 23m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:25 | 18:15 | mon, thu, fri | WN1972 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:30 | 18:31 | fri | AA2142 | American Eagle | 3h 1m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:44 | 18:50 | wed, sat | UA1828 | United Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:00 | 18:50 | sat | WN1972 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:24 | 19:44 | mon, thu, fri, sun | F93043 | Frontier (Klondike the Polar Bear) | 3h 20m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:37 | 19:44 | daily | AA3232 | American Eagle | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:20 | 20:10 | sun | WN1972 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:23 | 20:22 | thu, sat | F93853 | Frontier (Klondike the Polar Bear) | 2h 59m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:30 | 20:20 | sat | WN748 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:08 | 21:25 | mon, tue, wed, thu, fri, sun | AA1247 | American Eagle | 3h 17m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:12 | 21:22 | mon, fri | AA1247 | American Eagle | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:26 | 21:32 | sat | AA1247 | American Eagle | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:40 | 21:25 | sun | WN748 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:50 | 21:58 | sat | NK341 | Spirit Airlines | 3h 8m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:55 | 21:40 | tue | WN748 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:00 | 21:50 | sun | WN255 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:10 | 22:00 | sat | WN3726 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:15 | 22:05 | mon, thu, fri | WN3726 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:23 | 22:22 | mon, tue | NK2343 | Spirit Airlines | 2h 59m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:40 | 22:25 | mon | WN748 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:09 | 22:42 | mon, tue, wed, thu | 5X1327 | UPS | 2h 33m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:15 | 22:48 | mon, tue, wed, thu | 5X1327 | UPS | 2h 33m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:18 | 23:31 | fri | F92791 | Frontier (Klondike the Polar Bear) | 3h 13m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:25 | 23:15 | sat | WN2634 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:50 | 23:40 | mon, fri | WN2634 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:52 | 00:05 | mon | F92791 | Frontier (Klondike the Polar Bear) | 3h 13m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:55 | 23:45 | tue, wed | WN3726 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:10 | 23:55 | sun | WN3277 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |