Cheap Flights from MDW to ORL
The Cheapest Round-trip Tickets from to Orlando
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 1 November 2026 | 6 November 2026 | Direct |  | RT from 158 USD |
The Cheapest Flights for this Month from to Orlando
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 7 October 2026 | 11 October 2026 | 1 Stop | | RT from 360 USD |
| 13 October 2026 | 20 October 2026 | 1 Stop | | RT from 307 USD |
| 16 October 2026 | 18 October 2026 | 1 Stop |  | RT from 497 USD |
| 25 October 2026 | 27 October 2026 | 1 Stop | | RT from 222 USD |
| 31 October 2026 | 3 November 2026 | 1 Stop | | RT from 233 USD |
| 1 November 2026 | 6 November 2026 | 1 Stop | | RT from 158 USD |
| 7 November 2026 | 16 November 2026 | 2 Stops | | RT from 206 USD |
| 12 November 2026 | 15 November 2026 | 1 Stop | | RT from 312 USD |
| 13 November 2026 | 16 November 2026 | 1 Stop | | RT from 223 USD |
| 17 November 2026 | 20 November 2026 | 1 Stop | | RT from 246 USD |
| 17 December 2026 | 20 December 2026 | Direct | | RT from 278 USD |
| 19 December 2026 | 29 December 2026 | Direct | | RT from 234 USD |
| 23 December 2026 | 26 December 2026 | Direct | | RT from 230 USD |
| 18 February 2027 | 21 February 2027 | 1 Stop | | RT from 286 USD |
| 14 April 2027 | 18 April 2027 | Direct | | RT from 500 USD |
The Cheapest Flights from to Orlando for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 25 October 2026 | 27 October 2026 | 1 Stop | | RT from 222 USD |
| 1 November 2026 | 6 November 2026 | 1 Stop | | RT from 158 USD |
| 23 December 2026 | 26 December 2026 | Direct | | RT from 230 USD |
| 18 February 2027 | 21 February 2027 | 1 Stop | | RT from 286 USD |
| 14 April 2027 | 18 April 2027 | Direct | | RT from 500 USD |