Tap Air Portugal has round-trip flights from Chicago (ORD) to Tenerife, Canary Islands (TFS) for $441 with a connection. Flights January to February. Origin/Destination reversible.
Note: This fare will require an overnight stopover (22-hours) in Lisbon, on the return flight, which may work out for you if you’re wanting to check out both cities.
Note: 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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Read More Cheap Flights: Chicago to/from Tenerife, Canary Islands $441 r/t – Tap Air Portugal