Cheap Flights from CHI to BOS
The Cheapest Round-trip Tickets from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 24 October 2025 | 28 October 2025 | Direct |  | RT from 140 |
The Cheapest Flights for this Month from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 13 September 2025 | 14 September 2025 | Direct | | RT from 162 |
| 19 September 2025 | 22 September 2025 | Direct | | RT from 154 |
| 24 October 2025 | 28 October 2025 | Direct | | RT from 140 |
The Cheapest Flights from Chicago to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 19 September 2025 | 22 September 2025 | Direct | | RT from 154 |
| 24 October 2025 | 28 October 2025 | Direct | | RT from 140 |