Cheap Flights from MDW to BOS
The Cheapest Round-trip Tickets from to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 3 November 2026 | 7 November 2026 | Direct |  | RT from 200 USD |
The Cheapest Flights for this Month from to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 September 2026 | 22 September 2026 | Direct | | RT from 403 USD |
| 24 September 2026 | 28 September 2026 | 2 Stops | | RT from 462 USD |
| 25 September 2026 | 27 September 2026 | Direct | | RT from 656 USD |
| 3 October 2026 | 8 October 2026 | Direct | | RT from 349 USD |
| 5 October 2026 | 10 October 2026 | Direct | | RT from 406 USD |
| 6 October 2026 | 11 October 2026 | Direct | | RT from 310 USD |
| 7 October 2026 | 12 October 2026 | Direct | | RT from 361 USD |
| 8 October 2026 | 12 October 2026 | Direct | | RT from 361 USD |
| 9 October 2026 | 14 October 2026 | Direct | | RT from 415 USD |
| 29 October 2026 | 2 November 2026 | Direct | | RT from 261 USD |
| 3 November 2026 | 7 November 2026 | 1 Stop | | RT from 200 USD |
| 19 November 2026 | 22 November 2026 | Direct | | RT from 287 USD |
The Cheapest Flights from to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 September 2026 | 22 September 2026 | Direct | | RT from 403 USD |
| 29 October 2026 | 2 November 2026 | Direct | | RT from 261 USD |
| 3 November 2026 | 7 November 2026 | 1 Stop | | RT from 200 USD |