● Deals from
● Sweeping every destination…
$104usually $154−32%3 Nov 2026 · direct · score 78/100 · Exceptional
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 32% 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 96% of the 26 fares tracked for this route.
Questions people ask about this route
- What is the lowest price for a flight from Boston to Chicago right now?
- The lowest price our scan found today (2026-10-09) is $104 one-way fare, departing 3 Nov 2026, direct. Fares move constantly — the link below re-checks live availability on Aviasales.
- Is $104 a good price for a Boston to Chicago flight (BOS→CHI)?
- Yes by the data: this route usually costs about $154 (midpoint of Google Flights' typical price range), so $104 is 32% below usual and cheaper than 96% of the 26 fares tracked for this route. FareFloor's deal score for it is 78/100 as of 2026-10-09.
- When is the cheapest time to fly from Boston to Chicago in the coming months?
- Across the departure windows our 2026-10-09 scan compared, the lowest-priced departure found is 3 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 Boston to Chicago at this price?
- Yes — the $104 fare found today is a direct flight.