Using the online timetable is an easy way to look at all the direct flights Orlando — Chicago
428 flights in a week
Departure and arrival times are local (Orlando and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 00:30 | 03:24 | sun | UA3874 | United Express | 2h 54m | Orlando International Airport — O'Hare International Airport | Select dates |
| 05:01 | 06:56 | tue, thu, sun | F91457 | Frontier (Courtney the Cougar Livery) | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 05:05 | 07:00 | sun | F91457 | Frontier (Courtney the Cougar Livery) | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:05 | 08:00 | sat | WN2910 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:15 | 08:10 | thu, fri | WN2910 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 08:25 | tue, wed | WN2910 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 08:15 | thu | WN6125 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:31 | 08:53 | sat | F92041 | Frontier (Courtney the Cougar Livery) | 3h 22m | Orlando International Airport — O'Hare International Airport | Select dates |
| 06:40 | 08:45 | mon, tue, wed, thu, fri, sat | WN2078 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 06:40 | 08:40 | sun | WN2910 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 06:45 | 08:53 | daily | AA1856 | American Airlines | 3h 8m | Orlando International Airport — O'Hare International Airport | Select dates |
| 06:45 | 08:54 | mon, sun | AA1856 | American Airlines | 3h 9m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 08:59 | mon | UA224 | United Express | 2h 59m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:00 | 09:10 | tue, wed, fri, sun | AA557 | American Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:15 | 09:26 | mon, wed, thu, fri, sat, sun | UA1957 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:15 | 09:05 | tue, wed | WN5117 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:15 | 09:25 | sat | WN3648 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:20 | 09:15 | thu | WN2592 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:30 | 09:20 | tue, wed | WN137 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:30 | 09:34 | mon, tue, wed, fri | UA1957 | United Express | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:33 | 09:32 | daily | UA224 | United Express | 2h 59m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:34 | 09:38 | sat | UA1957 | United Express | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:35 | 09:38 | fri | UA2703 | United Express | 3h 3m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:35 | 09:30 | thu, fri | WN2592 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:40 | 09:35 | sat | WN1356 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:45 | 09:35 | sat | WN5117 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 07:50 | 09:54 | sun | UA1957 | United Express | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:55 | 10:00 | sun | WN2078 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 07:55 | 09:45 | thu | WN5117 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:00 | 09:54 | sun | UA3922 | United Express | 2h 54m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:25 | 10:10 | sat | WN1984 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:30 | 10:20 | sat | WN2592 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:45 | 10:55 | wed | AA9723 | American Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 08:50 | 10:54 | thu | F91457 | Frontier (Courtney the Cougar Livery) | 3h 4m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 08:55 | 10:50 | sun | WN1275 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:00 | 11:05 | sun | F91457 | Frontier (Courtney the Cougar Livery) | 3h 5m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:05 | 11:00 | tue, wed | WN1918 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:15 | 11:12 | sat | UA3900 | United Express | 2h 57m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:30 | 11:30 | tue, wed | WN934 | Southwest Airlines | 3h 0m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:35 | 11:46 | sat | NK3036 | Spirit Airlines | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:39 | 11:50 | daily | UA1941 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:45 | 11:30 | tue, wed | WN3156 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:50 | 12:01 | daily | UA1941 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:50 | 12:00 | sun | WN3567 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:50 | 11:45 | mon, thu, fri | WN374 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:50 | 11:35 | sat | WN3156 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 09:55 | 12:03 | daily | UA1941 | United Express | 3h 8m | Orlando International Airport — O'Hare International Airport | Select dates |
| 09:56 | 12:01 | mon, tue, thu, fri, sat, sun | NK1354 | Spirit Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:10 | 12:00 | sat | WN1936 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:15 | 12:05 | sat | WN374 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:29 | 12:31 | daily | AA2870 | American Airlines | 3h 2m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:30 | 12:41 | sat | UA307 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:34 | 12:42 | fri, sat | AA2142 | American Airlines | 3h 8m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:34 | 12:40 | daily | AA2142 | American Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:45 | 12:35 | tue, wed | WN3848 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:46 | 12:57 | thu | UA2421 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:50 | 13:00 | wed | WN3567 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:50 | 12:40 | thu, fri | WN3217 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 10:50 | 12:57 | mon, tue, wed, thu, sat, sun | UA2421 | United Express | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:55 | 13:06 | mon | UA2207 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:55 | 13:00 | mon, tue, wed, thu, fri | WN4204 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 10:55 | 13:01 | fri | UA2421 | United Express | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:00 | 13:11 | mon, thu, sat, sun | UA2421 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:00 | 13:10 | fri | UA2421 | United Express | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:00 | 12:50 | tue, wed | WN374 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:00 | 13:00 | mon, thu, fri | WN934 | Southwest Airlines | 3h 0m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:05 | 13:00 | sun | WN374 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:15 | 12:55 | mon, tue, wed, thu, fri | WN2657 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:15 | 13:00 | tue | WN6125 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:50 | 14:00 | sat, sun | WN4204 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 11:50 | 13:45 | sat | WN2133 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 11:55 | 14:00 | sun | WN3648 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:00 | 14:12 | mon, fri | F92041 | Frontier (Courtney the Cougar Livery) | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:00 | 13:49 | sat | UA3879 | United Express | 2h 49m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:20 | 14:25 | sat | WN934 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:39 | 14:45 | daily | UA2475 | United Express | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 12:40 | 14:25 | sat | WN3157 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:45 | 14:35 | wed | WN1964 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:49 | 14:53 | mon, wed, fri, sat | F91457 | Frontier (Courtney the Cougar Livery) | 3h 4m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 12:59 | 15:05 | mon, wed | F91457 | Frontier (Courtney the Cougar Livery) | 3h 6m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:00 | 14:45 | mon, thu, fri | WN2450 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:01 | 15:05 | fri, sat | F91457 | Frontier (Courtney the Cougar Livery) | 3h 4m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:25 | 15:35 | sun | WN3660 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 13:25 | 15:15 | sat, sun | WN3157 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:40 | 15:30 | mon, thu, fri | WN3065 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:50 | 15:40 | mon | WN2610 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 13:55 | 15:53 | mon, tue, wed, thu, fri, sun | AA2119 | American Airlines | 2h 58m | Orlando International Airport — O'Hare International Airport | Select dates |
| 13:58 | 16:09 | mon, wed, sat | NK3778 | Spirit Airlines | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:00 | 15:45 | tue, wed, thu, fri | WN2938 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:00 | 16:03 | sat | AA2119 | American Airlines | 3h 3m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:05 | 16:10 | tue, wed | AA1121 | American Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:15 | 16:25 | mon, tue, wed, thu, fri | WN3055 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:15 | 16:15 | sun | WN2610 | Southwest Airlines | 3h 0m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:30 | 16:20 | tue, wed | WN1153 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 14:40 | 16:45 | mon, wed, thu, fri | WN3650 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 14:45 | 16:30 | sat | WN3313 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:20 | 17:15 | wed | WN2593 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:32 | 17:20 | fri | G41333 | Allegiant Air | 2h 48m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 15:35 | 17:30 | sun | WN6537 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:35 | 17:25 | sun | WN3313 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:40 | 17:47 | sat | NK2056 | Spirit Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 15:41 | 17:37 | sun | F93853 | Frontier (Courtney the Cougar Livery) | 2h 56m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:55 | 17:50 | sat | WN1153 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 15:56 | 17:45 | mon | G42815 | Allegiant Air | 2h 49m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 16:10 | 18:15 | mon, tue, wed, thu | UA1828 | United Express | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:11 | 18:18 | sat | NK2056 | Spirit Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:15 | 18:05 | mon | WN2593 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:15 | 18:22 | mon, tue, thu, sat | UA1828 | United Express | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:18 | 18:07 | mon, fri | G42815 | Allegiant Air | 2h 49m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 16:20 | 18:15 | daily | UA1828 | United Express | 2h 55m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:21 | 18:31 | sat | NK2056 | Spirit Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:29 | 18:18 | mon, fri | G42815 | Allegiant Air | 2h 49m | Orlando Sanford International Airport — Chicago Rockford International Airport | Select dates |
| 16:30 | 18:35 | daily | UA1828 | United Express | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:41 | 18:44 | tue | F92969 | Frontier (Courtney the Cougar Livery) | 3h 3m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:42 | 18:52 | mon | NK793 | Spirit Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 16:45 | 18:40 | sun | WN908 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 16:55 | 18:58 | sun | F92969 | Frontier (Courtney the Cougar Livery) | 3h 3m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:00 | 18:43 | fri | UA3926 | United Express | 2h 43m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:00 | 18:55 | sat | WN998 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:05 | 19:08 | tue | F91889 | Frontier (Courtney the Cougar Livery) | 3h 3m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:25 | 19:15 | tue | WN908 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:27 | 19:37 | sat | AA1247 | American Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:30 | 19:35 | mon, wed, thu, fri, sun | AA1247 | American Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:30 | 19:27 | sat | F93853 | Frontier (Courtney the Cougar Livery) | 2h 57m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:35 | 19:44 | daily | NK793 | Spirit Airlines | 3h 9m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:37 | 19:40 | mon, thu, fri, sat, sun | AA1782 | American Airlines | 3h 3m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:40 | 19:51 | thu | UA1855 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:40 | 19:47 | sat | AA1247 | American Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:42 | 19:52 | mon, tue, sat | NK793 | Spirit Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:50 | 20:00 | sat | WN3660 | Southwest Airlines | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 17:50 | 19:53 | mon, thu, fri | F92969 | Frontier (Courtney the Cougar Livery) | 3h 3m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 17:55 | 20:06 | fri | UA2419 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:00 | 20:05 | sun | WN2876 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:00 | 19:50 | mon, fri | WN3158 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:01 | 20:11 | mon | UA1855 | United Express | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:05 | 20:16 | mon, thu, sat, sun | UA2419 | United Express | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:15 | 20:22 | daily | UA1871 | United Express | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:15 | 20:10 | sat | WN3158 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:23 | 20:21 | tue, wed | F91889 | Frontier (Courtney the Cougar Livery) | 2h 58m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:25 | 20:36 | wed, thu, fri, sat | NK793 | Spirit Airlines | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:27 | 20:35 | mon, tue, thu, fri, sat, sun | NK793 | Spirit Airlines | 3h 8m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:30 | 20:15 | mon, thu, fri | WN2604 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:40 | 20:25 | sun | WN851 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 18:50 | 20:55 | sun | WN3650 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 18:55 | 20:45 | tue, wed | WN2259 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:05 | 20:55 | tue, wed | WN2604 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:10 | 20:50 | tue, wed | WN851 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:10 | 21:00 | mon, fri | WN3159 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:16 | 21:27 | wed | NK2056 | Spirit Airlines | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:30 | 21:25 | sat | WN2604 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:38 | 21:50 | sun | NK2056 | Spirit Airlines | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:38 | 21:49 | thu | NK2056 | Spirit Airlines | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 19:45 | 21:35 | sun | WN2604 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 19:50 | 21:57 | tue | NK2056 | Spirit Airlines | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:00 | 21:50 | mon, thu, fri | WN1538 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:00 | 22:12 | tue | NK2056 | Spirit Airlines | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:05 | 21:50 | sat | WN2532 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:10 | 21:55 | wed | WN2532 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:20 | 22:32 | fri | NK2056 | Spirit Airlines | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:23 | 22:33 | daily | UA1621 | United Express | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:30 | 22:35 | sat | WN3055 | Southwest Airlines | 3h 5m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:30 | 22:29 | wed | UA3923 | United Express | 2h 59m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:35 | 22:31 | fri | F94719 | Frontier (Courtney the Cougar Livery) | 2h 56m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:40 | 22:35 | tue | WN1538 | Southwest Airlines | 2h 55m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:40 | 22:25 | sat | WN1328 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:45 | 22:52 | mon, thu, fri, sat, sun | UA1536 | United Express | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 20:45 | 22:41 | mon | F94719 | Frontier (Courtney the Cougar Livery) | 2h 56m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 20:45 | 22:29 | tue | F94719 | Frontier (Courtney the Cougar Livery) | 2h 44m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:00 | 23:10 | fri, sat | UA561 | United Express | 3h 10m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:00 | 22:52 | sat | UA3918 | United Express | 2h 52m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:15 | 22:42 | tue, thu | 5X1327 | UPS | 2h 27m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:15 | 22:48 | mon | 5X1327 | UPS | 2h 33m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:15 | 23:14 | tue, wed, thu | 5X1327 | UPS | 2h 59m | Orlando International Airport — Chicago Rockford International Airport | Select dates |
| 21:20 | 23:26 | mon | NK2056 | Spirit Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:20 | 23:10 | tue, wed | WN1328 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:23 | 23:21 | mon | F93853 | Frontier (Courtney the Cougar Livery) | 2h 58m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:30 | 23:20 | sun | WN1328 | Southwest Airlines | 2h 50m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:38 | 23:50 | thu, sun | NK2056 | Spirit Airlines | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:39 | 23:43 | mon, wed, fri, sat | F93043 | Frontier (Courtney the Cougar Livery) | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:40 | 23:20 | sun | WN2192 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:45 | 23:24 | sun | DL8922 | Delta Air Lines (SkyTeam Livery) | 2h 39m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:45 | 23:57 | tue | NK1992 | Spirit Airlines | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 21:45 | 23:30 | mon, thu, fri | WN1328 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 21:59 | 00:10 | thu | NK2056 | Spirit Airlines | 3h 11m | Orlando International Airport — O'Hare International Airport | Select dates |
| 22:00 | 23:40 | sun | WN2192 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:05 | 00:17 | mon, tue | NK2056 | Spirit Airlines | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 22:07 | 00:09 | thu | NK2056 | Spirit Airlines | 3h 2m | Orlando International Airport — O'Hare International Airport | Select dates |
| 22:10 | 00:22 | mon | NK1951 | Spirit Airlines | 3h 12m | Orlando International Airport — O'Hare International Airport | Select dates |
| 22:15 | 23:55 | sun | WN2192 | Southwest Airlines | 2h 40m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:15 | 00:19 | thu | UA3032 | United Express | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 22:20 | 00:05 | sun | WN2594 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:30 | 00:15 | sat | WN2594 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:35 | 00:20 | mon, tue, thu, fri, sat | WN2594 | Southwest Airlines | 2h 45m | Orlando International Airport — Chicago Midway International Airport | Select dates |
| 22:52 | 00:59 | mon, tue, thu, fri, sun | F92791 | Frontier (Courtney the Cougar Livery) | 3h 7m | Orlando International Airport — O'Hare International Airport | Select dates |
| 23:10 | 01:02 | mon | UA3891 | United Express | 2h 52m | Orlando International Airport — O'Hare International Airport | Select dates |
| 23:15 | 01:19 | tue | UA3865 | United Express | 3h 4m | Orlando International Airport — O'Hare International Airport | Select dates |
| 23:20 | 01:26 | mon, fri | NK2056 | Spirit Airlines | 3h 6m | Orlando International Airport — O'Hare International Airport | Select dates |