Today's drop ·
Cheap flights from Chicago to Madrid
$650 round trip right now, 25% under the $865 this route usually costs.
How cheap is this?
Telly prices every departure date in the next week 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 $650 on TAP Portugal, 1 stop, against a usual $865. 25% below the usual fare.
When to go
The cheapest dates fall in Nov, for trips of 12 nights. Nov in Madrid runs around 52°. 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
Madrid 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 to Madrid?+
Right now $650 round trip, on TAP Portugal. The route usually costs $865, so this fare is 25% under. Checked Nov 4, 2026.
When are the cheapest dates to fly to Madrid?+
The cheapest dates Telly found are in Nov, for trips of 12 nights. It prices every departure date in the next week on this route and keeps only the lowest. The exact dates are in the app.
Do I need a passport to fly from Chicago to Madrid?+
Yes. Madrid is outside the US and Canada, and every flight on Telly leaves the country, so every one needs a passport.
