This fare requires an overnight connection in Lisbon on the return flight.
Tap Air Portugal has round-trip flights from Chicago (ORD) to Tenerife (TFS) for $205-$241 with a connection. Flights February to June. No Tuesday departures. Origin/Destination reversible.
Carry on bag with a maximum weight of 17.6 lbs is allowed for free on TAP. You can avoid seat selection fees by accepting the randomly assigned seat at the gate.
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