Cheap Flights from Chicago to Boston
Compare cheap flights from Chicago (ORD) to Boston (BOS) on Tripile, with fares from around $89. The route takes about 2h 45m, and April is often the best month for low prices.
Airlines on This Route
Popular airlines flying Chicago to Boston include American Airlines, United, JetBlue, Spirit. Compare their schedules, baggage rules, and prices side by side, then book the option that fits your trip.
With 4 carriers commonly serving ORD to BOS, 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 45m sector.
When to Book ORD to BOS
Fares on this route start from around $89, and April typically brings the lowest prices. Search with flexible dates to compare a whole month at once, check the return leg from Boston to Chicago in the same search, and review the fare rules before paying so you know what a change or cancellation would cost.