Cheap Flights from MDW to BOS
The Cheapest Round-trip Tickets from to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 4 May 2026 | 10 May 2026 | Direct |  | RT from 148 |
The Cheapest Flights for this Month from to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 24 March 2026 | 30 March 2026 | Direct | | RT from 301 |
| 25 March 2026 | 27 March 2026 | Direct | | RT from 297 |
| 4 May 2026 | 10 May 2026 | Direct | | RT from 148 |
| 7 May 2026 | 10 May 2026 | Direct | | RT from 149 |
| 27 June 2026 | 29 June 2026 | 1 Stop | | RT from 308 |
| 23 July 2026 | 23 August 2026 | Direct | | RT from 377 |
| 7 September 2026 | 11 September 2026 | Direct | | RT from 369 |
| 16 October 2026 | 19 October 2026 | 1 Stop | | RT from 303 |
The Cheapest Flights from to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 25 March 2026 | 27 March 2026 | Direct | | RT from 297 |
| 4 May 2026 | 10 May 2026 | Direct | | RT from 148 |
| 27 June 2026 | 29 June 2026 | 1 Stop | | RT from 308 |
| 23 July 2026 | 23 August 2026 | Direct | | RT from 377 |
| 7 September 2026 | 11 September 2026 | Direct | | RT from 369 |
| 16 October 2026 | 19 October 2026 | 1 Stop | | RT from 303 |