Cheap flights from Chicago to Boston
The lowest fare found is €97. The cheapest month to fly is October.
Search live pricesSearch round-trip pricesLowest price by month
| October | €97 |
| November | €99 |
| December | €97 |
| January | €124 |
When is the cheapest time to fly from Chicago to Boston?
Fares are typically lowest in October, starting from €97.
Popular routes
- Chicago → Fort Lauderdale
- Chicago → Minneapolis
- Chicago → New York LaGuardia
- Chicago → Detroit
- Chicago → Philadelphia
- Chicago → Salt Lake City
- Chicago → San Diego
- Chicago → Baltimore
- Chicago → Tampa
- Chicago → Austin
- Chicago → Washington Dulles
- Chicago → Washington
Prices updated 2026-09-08