Cheap Flights from MDW to ORL
The Cheapest Round-trip Tickets from to Orlando
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 15 May 2026 | 18 May 2026 | Direct |  | RT from 135 |
The Cheapest Flights for this Month from to Orlando
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 April 2026 | 25 April 2026 | 1 Stop | | RT from 143 |
| 22 April 2026 | 29 April 2026 | 1 Stop | | RT from 214 |
| 24 April 2026 | 27 April 2026 | 1 Stop | | RT from 285 |
| 25 April 2026 | 27 April 2026 | 1 Stop | | RT from 239 |
| 1 May 2026 | 2 May 2026 | 1 Stop | | RT from 175 |
| 8 May 2026 | 11 May 2026 | 1 Stop | | RT from 191 |
| 15 May 2026 | 18 May 2026 | Direct | | RT from 135 |
| 22 May 2026 | 30 May 2026 | 1 Stop | | RT from 213 |
| 24 May 2026 | 31 May 2026 | 1 Stop | | RT from 317 |
| 1 June 2026 | 11 June 2026 | 1 Stop | | RT from 219 |
| 5 June 2026 | 8 June 2026 | 1 Stop | | RT from 213 |
| 8 June 2026 | 12 June 2026 | 1 Stop |  | RT from 246 |
| 10 June 2026 | 17 June 2026 | 1 Stop | | RT from 200 |
| 12 June 2026 | 14 June 2026 | 1 Stop | | RT from 324 |
| 6 August 2026 | 10 August 2026 | 1 Stop | | RT from 261 |
| 7 August 2026 | 10 August 2026 | 1 Stop | | RT from 261 |
| 8 August 2026 | 15 August 2026 | 1 Stop | | RT from 241 |
| 13 August 2026 | 17 August 2026 | 1 Stop | | RT from 389 |
| 17 December 2026 | 22 December 2026 | 2 Stops |  | RT from 975 |
The Cheapest Flights from to Orlando for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 April 2026 | 25 April 2026 | 1 Stop | | RT from 143 |
| 15 May 2026 | 18 May 2026 | Direct | | RT from 135 |
| 10 June 2026 | 17 June 2026 | 1 Stop | | RT from 200 |
| 8 August 2026 | 15 August 2026 | 1 Stop | | RT from 241 |
| 17 December 2026 | 22 December 2026 | 2 Stops | | RT from 975 |