Cheapest Day to Buy Flights from Chicago to Boston
Low Fare Calendar — Chicago to Boston
When to book vs. when to fly — Chicago → Boston
Live data from recent Aviasales searches for ORD → BOS, plus a booking rule of thumb.
Lowest indicative per-adult round-trip fares seen in Aviasales searches — confirmed live on the booking site before payment.
See the cheapest month’s fares ↗Search any date — Chicago → Boston
Flight options — Chicago → Boston
Recently-seen round-trip fares — click any flight for details, alternatives and booking.
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FAQ — ORD → BOS
How much is a flight from Chicago to Boston?
Prices vary by season and departure day. The Low Fare Calendar on this page shows the cheapest fare for every day of the coming year between Chicago (ORD) and Boston (BOS).
Which airlines fly from Chicago to Boston?
The Chicago → Boston route covers about 1,391 km and usually 1–3 h nonstop. Multiple carriers operate it — search FlyTiming to compare every airline and agency serving ORD → BOS in one search.
What is the cheapest day to fly from Chicago to Boston?
It varies by month. The price card on this page highlights the cheapest month and the historically cheapest day of the week to fly this route — the Low Fare Calendar below marks low-fare days in green.
When is the best time to book flights from Chicago to Boston?
As a rule of thumb, fares on international routes are usually lowest roughly 3–12 weeks before departure — and northern-summer peak (June–August) usually means the highest fares — book early or aim for the shoulder months. The calendar below is the fastest way to spot the cheapest months for Chicago → Boston.