Cheap Flights from Boston to Chicago
Compare cheap flights from Boston (BOS) to Chicago (ORD) on Tripile, with fares from around $99. The route takes about 2h 50m, and September is often the best month for low prices.
Airlines on This Route
Popular airlines flying Boston to Chicago include JetBlue, American Airlines, United, Spirit. Compare their schedules, baggage rules, and prices side by side, then book the option that fits your trip.
With 4 carriers commonly serving BOS to ORD, departure times are spread across the day, so it is worth checking early-morning and late-evening flights when you want the lowest fare on a 2h 50m sector.
When to Book BOS to ORD
Fares on this route start from around $99, and September typically brings the lowest prices. Search with flexible dates to compare a whole month at once, check the return leg from Chicago to Boston in the same search, and review the fare rules before paying so you know what a change or cancellation would cost.