Chicago O'Hare to Boston (ORD → BOS). We are tracking 8 fares on this route.
Cheapest tracked fare $95 · typical price $153 · you save about $58 (38%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
—
2026-10-24
1 stop
$95
—
2026-09-30
1 stop
$104
—
2026-10-15
1 stop
$104
—
2026-12-02
1 stop
$104
—
2026-10-16
1 stop
$104
—
2026-11-21
1 stop
$104
JetBlue
2026-11-23
Direct
$113
American Airlines
2026-09-05
Direct
$129
Could you save more?
The airport you were going to fly from is often not the cheapest one. Compare every airport in a region against each other, or check whether a multi-day stopover beats the direct fare.
How cheap can flights from Chicago O'Hare to Boston get?
The cheapest fare we have tracked on this route is $95, compared with a typical $153 for a trip of this distance.
Is it cheaper to fly to Boston from a different airport?
Often, yes. Fares out of secondary airports are frequently cheaper than the obvious hub, but they are the ones most likely to be missing from a normal search. Our reverse search compares every airport in a region against each other so the cheaper departure point is not hidden.
Could a stopover make Chicago O'Hare to Boston cheaper?
Sometimes. On thin long-haul routes a two-leg trip with a multi-day stopover can beat the direct fare, and occasionally a direct fare is not sold at all. Our detour search prices those routings against the direct flight.