Today's drop ·
Cheap flights from Chicago Midway to San José
$439 round trip right now, 33% under the $660 this route usually costs.
How cheap is this?
Telly prices every departure date six months out on this route, for trips of 2 to 14 nights, and measures each fare against what the route usually costs. The cheapest round trip right now is $439 on Delta Air Lines, 1 stop, against a usual $660. 33% below the usual fare.
When to go
The cheapest dates fall in Nov, for trips of 8 to 11 nights. Nov in San José runs around 77°. The dates come picked because a cheap fare only exists on certain days; the exact ones and the booking link are in the app.
Passport required
San José is outside the US and Canada, so you need a passport. Every flight on Telly leaves the country; that is the whole filter.
Questions about this route
How much is a flight from Chicago Midway to San José?+
Right now $439 round trip, on Delta Air Lines. The route usually costs $660, so this fare is 33% under. Checked Nov 4, 2026.
When are the cheapest dates to fly to San José?+
The cheapest dates Telly found are in Nov, for trips of 8 to 11 nights. It prices every departure date six months out on this route and keeps only the lowest. The exact dates are in the app.
Do I need a passport to fly from Chicago Midway to San José?+
Yes. San José is outside the US and Canada, and every flight on Telly leaves the country, so every one needs a passport.
