Cheap Flights from CHI to BOS
The Cheapest Round-trip Tickets from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 4 May 2026 | 10 May 2026 | Direct |  | RT from 142 |
The Cheapest Flights for this Month from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 16 April 2026 | 17 April 2026 | 1 Stop |  | RT from 307 |
| 26 April 2026 | 28 April 2026 | 1 Stop | | RT from 267 |
| 4 May 2026 | 10 May 2026 | Direct | | RT from 142 |
| 7 May 2026 | 10 May 2026 | Direct | | RT from 147 |
| 22 May 2026 | 25 May 2026 | Direct |  | RT from 242 |
| 24 September 2026 | 27 September 2026 | Direct | | RT from 237 |
| 25 September 2026 | 27 September 2026 | Direct | | RT from 238 |
The Cheapest Flights from Chicago to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 26 April 2026 | 28 April 2026 | 1 Stop | | RT from 267 |
| 4 May 2026 | 10 May 2026 | Direct | | RT from 142 |
| 24 September 2026 | 27 September 2026 | Direct | | RT from 237 |