Cheap Flights from MDW to BOS
The Cheapest Round-trip Tickets from to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 12 June 2026 | 15 June 2026 | Direct |  | RT from 202 |
The Cheapest Flights for this Month from to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 4 May 2026 | 10 May 2026 | Direct | | RT from 311 |
| 8 May 2026 | 10 May 2026 | Direct | | RT from 271 |
| 23 May 2026 | 26 May 2026 | 1 Stop | | RT from 221 |
| 31 May 2026 | 31 May 2026 | Direct | | RT from 414 |
| 1 June 2026 | 3 June 2026 | Direct | | RT from 262 |
| 3 June 2026 | 7 June 2026 | Direct | | RT from 214 |
| 12 June 2026 | 15 June 2026 | Direct | | RT from 202 |
| 23 August 2026 | 29 August 2026 | Direct | | RT from 207 |
| 23 October 2026 | 26 October 2026 | Direct | | RT from 221 |
| 25 October 2026 | 26 October 2026 | Direct | | RT from 221 |
The Cheapest Flights from to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 23 May 2026 | 26 May 2026 | 1 Stop | | RT from 221 |
| 12 June 2026 | 15 June 2026 | Direct | | RT from 202 |
| 23 August 2026 | 29 August 2026 | Direct | | RT from 207 |
| 23 October 2026 | 26 October 2026 | Direct | | RT from 221 |