Boston to Chicago O'Hare (BOS → ORD). We are tracking 15 fares on this route.
Cheapest tracked fare $88 · typical price $139 · you save about $51 (37%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
JetBlue
2026-11-04
Direct
$88
JetBlue
2026-11-09
Direct
$88
—
2026-10-28
1 stop
$89
—
2026-11-11
1 stop
$89
JetBlue
2026-11-02
Direct
$89
—
2026-11-18
1 stop
$89
—
2026-12-03
1 stop
$95
—
2026-12-05
1 stop
$95
Frontier Airlines
2026-10-27
1 stop
$95
JetBlue
2026-12-07
Direct
$105
JetBlue
2026-12-08
Direct
$105
JetBlue
2026-12-12
Direct
$105
Frontier Airlines
2026-10-24
1 stop
$108
JetBlue
2026-10-22
Direct
$110
Frontier Airlines
2026-10-21
1 stop
$113
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 Boston to Chicago O'Hare get?
The cheapest fare we have tracked on this route is $88, compared with a typical $139 for a trip of this distance.
Is it cheaper to fly to Chicago O'Hare 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 Boston to Chicago O'Hare 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.