Flying from Boston to Chicago, Il can be expensive. Our search helps you compare cheap flights, airfare deals, and flight tickets across airlines and agencies so you can book at the best price.
We scan trusted travel agencies and airline booking systems for the route Boston - Chicago, Il (BOS - ORD). We do not sell tickets or add fees - you choose where to buy.
Airfares vary by date, time, and airport. Use filters to find the best option by departure/arrival time, number of stops, airline or alliance, and booking channel.
If your dates are flexible, check the low-fare calendar to find the cheapest days. Booking round-trip in one order often reduces fees, and prices usually rise as departure approaches.
We also recommend you to look through the prices for return tickets from Chicago, Il to Boston.
Average round-trip airfares from Boston to Chicago, Il by months
| Month | Round-Trip |
|---|---|
| January 2026 | find now |
| February 2026 | 08.02 - 09.02from A$120 |
| March 2026 | find now |
| April 2026 | find now |
| May 2026 | find now |
| June 2026 | 26.06 - 28.06from A$398 |
| July 2026 | find now |
| August 2026 | 04.08 - 09.08from A$270 |
| September 2026 | find now |
| October 2026 | find now |
| November 2026 | find now |
| December 2026 | find now |
Prices shown are based on searches from the last few days. Ticket prices can change and depend on availability at the time of booking.
Airlines are flying from Boston to Chicago, Il
| American Airlines | JetBlue Airways | United Airlines |