Cheap flights from Boston to Chicago (All Airports)
Boston to Chicago (All Airports) (BOS → CHI). We are tracking 10 fares on this route.
Cheapest tracked fare $90 · typical price $152 · you save about $62 (41%)
Cheapest fares we're tracking
Airline
Departs
Stops
Price
—
2026-10-10
Direct
$90
Southwest
2026-10-05
Direct
$95
Southwest
2026-10-26
Direct
$95
United
2026-11-02
Direct
$95
—
2026-11-09
Direct
$95
JetBlue
2026-11-16
Direct
$95
Southwest
2026-11-23
Direct
$95
Delta
2026-12-14
Direct
$95
—
2026-10-06
Direct
$96
United
2026-10-19
1 stop
$105
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 (All Airports) get?
The cheapest fare we have tracked on this route is $90, compared with a typical $152 for a trip of this distance.
Is it cheaper to fly to Chicago (All Airports) 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 (All Airports) 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.