● Deals from
● Sweeping every destination…
$109usually $131−17%23 Sept 2026 · 1-stop · score 57/100 · Solid
Why so cheap?
This fare is below usual but under our auto-research threshold — ask and we’ll find the reason now, with sources.
Fares by departure date
Today’s fare is cheaper than 96% of the 25 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 (2026-08-29) is $109 one-way fare, departing 23 Sept 2026, 1-stop. Fares move constantly — the link below re-checks live availability on Aviasales.
- Is $109 a good price for a Boston to Chicago flight (BOS→CHI)?
- Yes by the data: this route usually costs about $131 (midpoint of Google Flights' typical price range), so $109 is 17% below usual and cheaper than 96% of the 25 fares tracked for this route. FareFloor's deal score for it is 57/100 as of 2026-08-29.
- When is the cheapest time to fly from Boston to Chicago in the coming months?
- Across the departure windows our 2026-08-29 scan compared, the lowest-priced departure found is 23 Sept 2026 at $109 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?
- The cheapest fare found today is 1-stop. A direct option, where one exists, may cost more — check the live fare link for alternatives.