Cheap Flights from CHI to BOS
The Cheapest Round-trip Tickets from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 17 September 2026 | 19 September 2026 | Direct |  | RT from 205 |
The Cheapest Flights for this Month from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 1 September 2026 | 6 September 2026 | Direct | | RT from 336 |
| 6 September 2026 | 8 September 2026 | Direct | | RT from 339 |
| 15 September 2026 | 19 September 2026 | 1 Stop | | RT from 264 |
| 17 September 2026 | 19 September 2026 | Direct | | RT from 205 |
| 19 September 2026 | 21 September 2026 | 1 Stop |  | RT from 241 |
| 29 September 2026 | 4 October 2026 | Direct |  | RT from 228 |
| 21 October 2026 | 24 October 2026 | 1 Stop | | RT from 205 |
| 29 October 2026 | 1 November 2026 | Direct |  | RT from 256 |
| 27 November 2026 | 1 December 2026 | Direct | | RT from 280 |
| 17 April 2027 | 20 April 2027 | Direct | | RT from 280 |
The Cheapest Flights from Chicago to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 17 September 2026 | 19 September 2026 | Direct | | RT from 205 |
| 21 October 2026 | 24 October 2026 | 1 Stop | | RT from 205 |
| 27 November 2026 | 1 December 2026 | Direct | | RT from 280 |
| 17 April 2027 | 20 April 2027 | Direct | | RT from 280 |