Using the online timetable is an easy way to look at all the direct flights Orlando — Chicago
274 flights in a week
Departure and arrival times are local (Orlando and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:45 | 08:40 | sun | WN2300 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 09:18 | mon, fri, sat, sun | UA1097 | United Express | 3h 18m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:10 | 09:10 | sat | WN2300 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:15 | mon, tue, wed, thu, fri | WN2300 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:20 | 09:36 | tue | AA1585 | American Eagle | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:24 | 09:40 | mon, fri | AA1585 | American Eagle | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:29 | 09:45 | wed | AA1585 | American Eagle | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:30 | 09:45 | mon, tue, thu, fri, sat, sun | WN3882 | Southwest Airlines | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:35 | 09:24 | sat | G42955 | Allegiant Air | 2h 49m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 07:44 | 10:00 | sat, sun | AA1585 | American Eagle | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:50 | 10:06 | thu | AA1585 | American Eagle | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:00 | 10:16 | tue | AA1360 | American Eagle | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:00 | 09:49 | mon, fri | G42873 | Allegiant Air | 2h 49m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 08:10 | 10:20 | wed | AA3051 | American Eagle | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:10 | 10:00 | sun | WN4729 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:15 | 10:31 | wed | AA1360 | American Eagle | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:30 | 10:25 | tue, wed | WN3883 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:35 | 10:30 | sat | WN2540 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:00 | 11:15 | wed | AA1023 | American Eagle | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:18 | 11:31 | sat | UA2341 | United Express | 3h 13m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:26 | 11:39 | mon, tue, wed, thu, fri, sun | UA2341 | United Express | 3h 13m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:48 | 12:00 | sat | UA1470 | United Express | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:05 | 12:00 | mon, thu, fri | WN1669 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:10 | 12:05 | tue, wed | WN1669 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:15 | 12:10 | sun | WN2540 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:26 | 12:36 | daily | AA2998 | American Eagle | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:48 | 13:03 | mon, tue, sat | UA2207 | United Express | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:50 | 13:05 | wed, thu, sun | UA2207 | United Express | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:05 | 13:08 | fri, sat | F93853 | Frontier (Penny the Owl Livery) | 3h 3m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:40 | 13:35 | mon, thu, fri | WN3862 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:55 | 13:50 | tue, wed | WN3862 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:00 | 13:55 | mon, thu, fri, sun | WN4661 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:05 | 13:54 | wed | G42821 | Allegiant Air | 2h 49m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 12:12 | 14:29 | mon, tue, wed, sat | UA2475 | United Express | 3h 17m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:12 | 14:27 | sun | UA2475 | United Express | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:15 | 14:10 | sun | WN3291 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:15 | 14:21 | mon | F93853 | Frontier (Penny the Owl Livery) | 3h 6m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:25 | 14:40 | mon, tue, thu, fri, sat, sun | UA2475 | United Express | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:40 | 14:52 | sun | AA1511 | American Eagle | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:45 | 14:40 | sat | WN1669 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:50 | 14:45 | mon, thu, fri | WN1739 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:55 | 14:50 | mon, tue, thu, sun | WN4661 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:06 | 15:25 | mon | F93043 | Frontier (Penny the Owl Livery) | 3h 19m | Orlando International Airport — O'Hare International Airport | Select dates |
| 13:09 | 15:28 | mon, tue, wed, thu, fri, sun | F93043 | Frontier (Penny the Owl Livery) | 3h 19m | Orlando International Airport — O'Hare International Airport | Select dates |
| 13:19 | 15:38 | wed | F93043 | Frontier (Penny the Owl Livery) | 3h 19m | Orlando International Airport — O'Hare International Airport | Select dates |
| 13:31 | 15:33 | tue | F93853 | Frontier (Penny the Owl Livery) | 3h 2m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:50 | 15:52 | sun | F93853 | Frontier (Penny the Owl Livery) | 3h 2m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:55 | 15:50 | sun | WN3862 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:10 | 16:21 | mon, tue, wed | AA3031 | American Eagle | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:11 | 16:23 | daily | AA2877 | American Eagle | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:22 | 16:38 | mon, tue, thu, sat | UA2481 | United Express | 3h 16m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:30 | 16:52 | sat | F93043 | Frontier (Penny the Owl Livery) | 3h 22m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:35 | 16:30 | tue, wed | WN4661 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:50 | 17:05 | mon, tue, wed, sat, sun | UA2147 | United Express | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:50 | 16:45 | sat | WN3862 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:50 | 16:56 | mon, wed, thu, fri, sun | NK1606 | Spirit Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 15:40 | 17:44 | thu | F91457 | Frontier (Penny the Owl Livery) | 3h 4m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:50 | 17:45 | tue, wed | WN498 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:55 | 18:10 | daily | UA2628 | United Express | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:05 | 18:13 | tue, wed | F91457 | Frontier (Penny the Owl Livery) | 3h 8m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:15 | 18:35 | mon, tue, thu, sat, sun | WN1535 | Southwest Airlines | 3h 20m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:21 | 18:35 | tue, wed | AA2877 | American Eagle | 3h 14m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:26 | 18:43 | mon, tue, thu, sat, sun | UA2071 | United Express | 3h 17m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:31 | 18:45 | sat | AA2492 | American Eagle | 3h 14m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:35 | 18:50 | fri, sun | UA2071 | United Express | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:40 | 18:35 | sat | WN823 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:45 | 18:40 | tue, wed | WN1733 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:45 | 18:45 | sat | WN4015 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:55 | 18:55 | sun | WN3587 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:00 | 19:05 | mon, thu, fri | WN4015 | Southwest Airlines | 3h 5m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:20 | 19:15 | mon, thu, fri | WN2574 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:20 | 19:20 | tue, wed | WN4015 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:28 | 19:41 | mon, wed, sun | NK393 | Spirit Airlines | 3h 13m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:34 | 19:47 | daily | NK393 | Spirit Airlines | 3h 13m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:35 | 19:30 | sat | WN1823 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:46 | 20:00 | wed, thu, fri, sun | AA2492 | American Eagle | 3h 14m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:50 | 19:45 | sat | WN2574 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:50 | 20:03 | tue, wed, fri, sat, sun | NK393 | Spirit Airlines | 3h 13m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:08 | 20:25 | tue, wed, thu, fri, sat, sun | UA1209 | United Express | 3h 17m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:12 | 20:22 | mon | UA583 | United Express | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:15 | 20:32 | mon | UA2662 | United Express | 3h 17m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:15 | 20:15 | mon, thu, fri | WN1254 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:25 | 20:25 | sun | WN4015 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:48 | 20:53 | mon, fri | F91457 | Frontier (Penny the Owl Livery) | 3h 5m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:50 | 20:50 | tue, wed | WN1254 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:12 | 21:21 | daily | AA3243 | American Eagle | 3h 9m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:15 | 21:10 | mon, thu, fri | WN3155 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:40 | 21:50 | daily | WN897 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:40 | 21:55 | daily | WN2617 | Southwest Airlines | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:42 | 21:45 | sat | F91457 | Frontier (Penny the Owl Livery) | 3h 3m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:55 | 21:55 | sat | WN3155 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:59 | 22:00 | sun | WN3155 | Southwest Airlines | 3h 1m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:35 | 22:25 | mon | WN1733 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:40 | 22:57 | tue, wed, thu, fri, sat | UA583 | United Express | 3h 17m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:40 | 22:40 | tue, wed | WN3155 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:00 | 23:09 | mon, tue, wed, thu, fri, sun | AA893 | American Eagle | 3h 9m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:00 | 23:15 | mon | F92791 | Frontier (Penny the Owl Livery) | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:06 | 23:15 | sat | AA893 | American Eagle | 3h 9m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:09 | 22:45 | tue, wed, thu | 5X1327 | UPS | 2h 36m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:09 | 22:46 | mon, tue, wed | 5X1327 | UPS | 2h 37m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:09 | 22:51 | mon | 5X1327 | UPS | 2h 42m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:09 | 22:50 | tue | 5X1327 | UPS | 2h 41m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:23 | 23:38 | mon, tue, wed, fri, sat, sun | F92791 | Frontier (Penny the Owl Livery) | 3h 15m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:55 | 23:50 | sat | WN1780 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:50 | 00:45 | tue, fri, sat | WN416 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:55 | 00:50 | mon | WN416 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |