Flight schedule from Chicago Midway International Airport
| Flight | Flight days | Departure | Arrival | Flight time | Airlines | Price | ||
|---|---|---|---|---|---|---|---|---|
| WN3657 | Chicago — Albuquerque | tue, wed | 10:10 | 12:20 | 3h 10m | Southwest Airlines | search | |
| WN3657 | Chicago — Albuquerque | sat | 19:50 | 22:00 | 3h 10m | Southwest Airlines | search | |
| WN2931 | Chicago — Atlanta | tue, wed | 08:05 | 11:00 | 1h 55m | Southwest Airlines | search | |
| WN1440 | Chicago — Atlanta | sat | 12:45 | 15:35 | 1h 50m | Southwest Airlines | search | |
| WN1440 | Chicago — Atlanta | tue, wed | 12:50 | 15:45 | 1h 55m | Southwest Airlines | search | |
| WN1440 | Chicago — Atlanta | mon, thu, fri, sun | 12:55 | 15:50 | 1h 55m | Southwest Airlines | search | |
| WN2648 | Chicago — Austin | tue, wed | 19:55 | 22:50 | 2h 55m | Southwest Airlines | search | |
| WN2648 | Chicago — Austin | mon | 20:30 | 23:20 | 2h 50m | Southwest Airlines | search | |
| WN3913 | Chicago — Baltimore | tue, wed, sat | 09:20 | 12:05 | 1h 45m | Southwest Airlines | search | |
| WN2392 | Chicago — Baltimore | sat | 14:10 | 16:55 | 1h 45m | Southwest Airlines | search | |
| WN3913 | Chicago — Baltimore | mon | 21:15 | 00:05 | 1h 50m | Southwest Airlines | search | |
| WN3913 | Chicago — Baltimore | fri | 21:40 | 00:25 | 1h 45m | Southwest Airlines | search | |
| WN2407 | Chicago — Birmingham | mon, thu, fri | 12:10 | 13:50 | 1h 40m | Southwest Airlines | search | |
| WN3352 | Chicago — Boston | sat, sun | 07:40 | 10:55 | 2h 15m | Southwest Airlines | from $102 | search |
| WN3352 | Chicago — Boston | thu | 07:50 | 11:05 | 2h 15m | Southwest Airlines | from $102 | search |
| WN3352 | Chicago — Boston | mon, thu, fri | 07:55 | 11:10 | 2h 15m | Southwest Airlines | from $102 | search |
| WN3352 | Chicago — Boston | tue, wed | 08:00 | 11:20 | 2h 20m | Southwest Airlines | from $102 | search |
| WN3490 | Chicago — Buffalo | tue, wed | 07:45 | 10:10 | 1h 25m | Southwest Airlines | search | |
| WN3490 | Chicago — Buffalo | sat | 07:50 | 10:15 | 1h 25m | Southwest Airlines | search | |
| WN3490 | Chicago — Buffalo | mon, thu, fri | 08:00 | 10:30 | 1h 30m | Southwest Airlines | search | |
| WN4601 | Chicago — Cincinnati | sat | 12:45 | 14:55 | 1h 10m | Southwest Airlines | search | |
| WN4601 | Chicago — Cincinnati | sun | 12:55 | 15:05 | 1h 10m | Southwest Airlines | search | |
| WN4601 | Chicago — Cincinnati | tue, wed | 13:20 | 15:30 | 1h 10m | Southwest Airlines | search | |
| WN4601 | Chicago — Cincinnati | mon, thu | 13:25 | 15:35 | 1h 10m | Southwest Airlines | search | |
| WN4008 | Chicago — Cleveland | mon, thu, fri, sat | 08:00 | 10:15 | 1h 15m | Southwest Airlines | search | |
| WN2536 | Chicago — Cleveland | tue, wed | 18:00 | 20:10 | 1h 10m | Southwest Airlines | search | |
| WN2536 | Chicago — Cleveland | mon, thu, fri | 18:45 | 20:55 | 1h 10m | Southwest Airlines | search | |
| WN2536 | Chicago — Cleveland | sat | 18:55 | 21:05 | 1h 10m | Southwest Airlines | search | |
| WN2536 | Chicago — Cleveland | sun | 19:20 | 21:35 | 1h 15m | Southwest Airlines | search | |
| WN3102 | Chicago — Dallas | thu, sat | 18:59 | 21:30 | 2h 31m | Southwest Airlines | search | |
| WN3102 | Chicago — Dallas | thu | 19:00 | 21:30 | 2h 30m | Southwest Airlines | search | |
| WN3102 | Chicago — Dallas | sun | 19:25 | 21:55 | 2h 30m | Southwest Airlines | search | |
| WN3102 | Chicago — Dallas | tue, wed | 20:35 | 23:05 | 2h 30m | Southwest Airlines | search | |
| WN3262 | Chicago — Denver | mon, thu, fri, sat, sun | 06:00 | 07:40 | 2h 40m | Southwest Airlines | search | |
| WN3262 | Chicago — Denver | tue, wed | 06:30 | 08:10 | 2h 40m | Southwest Airlines | search | |
| WN3036 | Chicago — Denver | sat | 08:30 | 10:25 | 2h 55m | Southwest Airlines | search | |
| WN3008 | Chicago — Denver | tue, thu, sun | 11:20 | 13:05 | 2h 45m | Southwest Airlines | search | |
| WN2965 | Chicago — Denver | mon, thu, fri, sat | 21:35 | 23:15 | 2h 40m | Southwest Airlines | search | |
| WN2965 | Chicago — Denver | mon, thu, fri | 21:40 | 23:20 | 2h 40m | Southwest Airlines | search | |
| WN2965 | Chicago — Denver | sun | 22:05 | 23:45 | 2h 40m | Southwest Airlines | search | |
| WN8512 | Chicago — Detroit | sat | 11:44 | 13:39 | 55m | Southwest Airlines | search | |
| WN2115 | Chicago — Fort Lauderdale | sat | 12:15 | 16:10 | 2h 55m | Southwest Airlines | search | |
| WN3992 | Chicago — Fort Myers | mon, thu, fri | 09:00 | 12:50 | 2h 50m | Southwest Airlines | search | |
| WN3992 | Chicago — Fort Myers | sun | 09:05 | 12:50 | 2h 45m | Southwest Airlines | search | |
| WN3992 | Chicago — Fort Myers | tue, wed | 09:15 | 13:00 | 2h 45m | Southwest Airlines | search | |
| WN2786 | Chicago — Fort Myers | tue, wed | 16:45 | 20:30 | 2h 45m | Southwest Airlines | search | |
| G43086 | Chicago — Fort Walton Beach | thu, sun | 21:13 | 23:21 | 2h 8m | Allegiant Air | search | |
| WN114 | Chicago — Grand Rapids | tue, wed | 20:35 | 22:30 | 55m | Southwest Airlines | search | |
| WN114 | Chicago — Grand Rapids | mon, thu, fri | 21:40 | 23:35 | 55m | Southwest Airlines | search | |
| WN114 | Chicago — Grand Rapids | sun | 21:50 | 23:45 | 55m | Southwest Airlines | search | |