Cheap Flights from CHI to BOS
The Cheapest Round-trip Tickets from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 6 August 2026 | 11 August 2026 | Direct |  | RT from 191 |
The Cheapest Flights for this Month from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 16 July 2026 | 20 July 2026 | Direct |  | RT from 308 |
| 17 July 2026 | 19 July 2026 | Direct | | RT from 301 |
| 6 August 2026 | 11 August 2026 | 1 Stop | | RT from 191 |
| 11 August 2026 | 11 August 2026 | Direct | | RT from 197 |
| 28 October 2026 | 30 October 2026 | 1 Stop | | RT from 203 |
| 30 October 2026 | 1 November 2026 | Direct |  | RT from 221 |
The Cheapest Flights from Chicago to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 17 July 2026 | 19 July 2026 | Direct | | RT from 301 |
| 6 August 2026 | 11 August 2026 | 1 Stop | | RT from 191 |
| 28 October 2026 | 30 October 2026 | 1 Stop | | RT from 203 |