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.