● Deals from
● Sweeping every destination…
$104usually $142−27%14 Nov 2026 · direct · score 74/100 · Solid
Live check · This route is not on today’s below-usual board, so we re-scanned it just now: the current cheapest upcoming fare sits about 27% below its usual level.
Why so cheap?
Researching this route’s pricing right now — checking season, sales, capacity and route news…
Fares by departure date
Today’s fare is cheaper than 97% of the 35 fares tracked for this route.
Questions people ask about this route
- What is the lowest price for a flight from Chicago to Boston right now?
- The lowest price our scan found today (2026-10-23) is $104 one-way fare, departing 14 Nov 2026, direct. Fares move constantly — the link below re-checks live availability on Aviasales.
- Is $104 a good price for a Chicago to Boston flight (ORD→BOS)?
- Yes by the data: this route usually costs about $142 (midpoint of Google Flights' typical price range), so $104 is 27% below usual and cheaper than 97% of the 35 fares tracked for this route. FareFloor's deal score for it is 74/100 as of 2026-10-23.
- When is the cheapest time to fly from Chicago to Boston in the coming months?
- Across the departure windows our 2026-10-23 scan compared, the lowest-priced departure found is 14 Nov 2026 at $104 one-way fare. Method: we sweep this origin's destinations several times a day via Google Flights data and keep the cheapest round-trip window per route — a cheaper window can appear any day, so treat this as today's answer, not a permanent one.
- Is there a direct flight from Chicago to Boston at this price?
- Yes — the $104 fare found today is a direct flight.