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 | 8 May 2026 | Direct |  | RT from 169 |
The Cheapest Flights for this Month from Chicago to Boston
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 25 April 2026 | 27 April 2026 | 1 Stop | | RT from 386 |
| 4 May 2026 | 8 May 2026 | Direct | | RT from 169 |
| 1 June 2026 | 7 June 2026 | Direct |  | RT from 182 |
| 4 June 2026 | 7 June 2026 | Direct | | RT from 181 |
The Cheapest Flights from Chicago to Boston for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 25 April 2026 | 27 April 2026 | 1 Stop | | RT from 386 |
| 4 May 2026 | 8 May 2026 | Direct | | RT from 169 |
| 4 June 2026 | 7 June 2026 | Direct | | RT from 181 |