Cheap flights from Orlando to Chicago
Find cheap Chicago to Orlando flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Orlando.
Orlando to Chicago flight schedules
| Flight | Departure Date | Arrival Date | Price | Duration | Number of stops | Updated |
|---|---|---|---|---|---|---|
| Orlando (ORL) - Chicago (CHI) | 2026-05-17 | 2026-05-17 | 227 USD | 5 hours 30 minutes | Direct | 2026-01-11T22:35:27 |
Orlando to Chicago flight status
| Flight | Origin | Destination | Departure | Arrival | Equip |
|---|---|---|---|---|---|
| WN4302 | Orlando (MCO) | Chicago (MDW) | 5:05 p.m. | 12:10 a.m. | B738 |
| WN1456 | Orlando (MCO) | Chicago (MDW) | 5:25 p.m. | 7:50 p.m. | B737 |
| WN1987 | Orlando (MCO) | Chicago (MDW) | 5:20 p.m. | 6:50 p.m. | B737 |
| WN2395 | Orlando (MCO) | Chicago (MDW) | 9:10 a.m. | 2:40 p.m. | B737 |
| WN565 | Orlando (MCO) | Chicago (MDW) | 9:35 a.m. | 12:05 p.m. | B737 |
| WN1664 | Orlando (MCO) | Chicago (MDW) | 12:15 p.m. | 1:40 p.m. | B737 |
| WN2164 | Orlando (MCO) | Chicago (MDW) | 4:45 p.m. | 5:45 p.m. | B737 |
| WN4259 | Orlando (MCO) | Chicago (MDW) | 7:45 p.m. | 10:15 p.m. | B737 |
| WN3496 | Orlando (MCO) | Chicago (MDW) | 11:55 a.m. | 12:40 p.m. | B737 |
| WN2985 | Orlando (MCO) | Chicago (MDW) | 3 p.m. | 4:20 p.m. | B737 |
| WN2810 | Orlando (MCO) | Chicago (MDW) | 3:15 p.m. | 5:35 p.m. | Boeing 737-800 (winglets) |
| WN3423 | Orlando (MCO) | Chicago (MDW) | 6:30 a.m. | 7:45 a.m. | B737 |
| WN2427 | Orlando (MCO) | Chicago (MDW) | 4:10 p.m. | 5:40 p.m. | Boeing 737-800 (winglets) |
| WN3313 | Orlando (MCO) | Chicago (MDW) | 4:55 p.m. | 6:30 p.m. | B738 |
| BR0696 | Orlando (MCO) | Chicago (MDW) | 9 a.m. | 12:50 a.m. | |
| WN4404 | Orlando (MCO) | Chicago (MDW) | 8:45 a.m. | 11 a.m. | B737 |
| WN4610 | Orlando (MCO) | Chicago (MDW) | 2 p.m. | 3:10 p.m. | B738 |
| WN59 | Orlando (MCO) | Chicago (MDW) | 4:25 p.m. | 5:55 p.m. | B737 |
| WN4827 | Orlando (MCO) | Chicago (MDW) | 9:30 a.m. | 1:20 p.m. | B738 |
| WN4104 | Orlando (MCO) | Chicago (MDW) | 10:25 a.m. | 12:20 p.m. | B738 |
| FR5033 | Orlando (MCO) | Chicago (MDW) | 9:20 p.m. | 10:15 p.m. | 73H |
| WN6432 | Orlando (MCO) | Chicago (MDW) | 3 p.m. | 4:45 p.m. | B738 |
| WN6313 | Orlando (MCO) | Chicago (MDW) | 10 a.m. | 11:35 a.m. | B737 |
| WN6817 | Orlando (MCO) | Chicago (MDW) | 3:15 p.m. | 4:45 p.m. | B738 |
| WN6191 | Orlando (MCO) | Chicago (MDW) | 6:10 a.m. | 8:05 a.m. | B738 |
| WN2692 | Orlando (MCO) | Chicago (MDW) | 1:30 p.m. | 2:50 p.m. | B737 |
| WN5704 | Orlando (MCO) | Chicago (MDW) | 5 a.m. | 6:35 a.m. | B737 |
| WN6773 | Orlando (MCO) | Chicago (MDW) | 11:55 a.m. | 1:40 p.m. | B737 |
| AX5030 | Orlando (MCO) | Chicago (MDW) | 12:05 p.m. | 2:10 p.m. | ER4 |
| BGM561 | Orlando (MCO) | Chicago (MDW) | 9:05 p.m. | 10:55 p.m. | CR2 |
| US2858 | Orlando (MCO) | Chicago (MDW) | 2:10 p.m. | 7:30 p.m. | CR9 |
| C31068 | Orlando (MCO) | Chicago (MDW) | 9:25 p.m. | 10:50 p.m. | |
| FL223 | Orlando (MCO) | Chicago (MDW) | 7:45 p.m. | 9:35 p.m. |
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