[03/04/2021 @ 12:35 PM CT] Fare gone. Expired.
Tap Air Portugal has round-trip flights from Chicago (ORD) to Porto (OPO) for $147 with a connection. Flights October to January. Weekends available.
Travel to Portugal is currently not allowed for US Citizens. Only Portuguese residents are allowed. This may work out for late 2021 and 2022 dates depending on how things go with covid restrictions moving forward.