Chicago to Madrid, Spain for only $376 roundtrip

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Cheap flights from Chicago to Madrid, Spain for only $376 roundtrip with TAP Air Portugal.

DEPART:
Chicago, USA

ARRIVE:
Madrid, Spain

RETURN:
Chicago, USA

DATES:
Availability from November 2025 to February 2026 (excluding Christmas/New Year)

Example dates:
14th-21st Nov
16th-23rd Nov
28th Nov – 5th Dec
28th Jan – 4th Feb
4th-11th Feb
11th-18th Feb
–
More dates are available for $382 roundtrip:
5th-12th Nov
12th-19th Nov
21st-28th Jan
30th Jan – 6th Feb

and more…

STOPS:
Lisbon

AIRLINES:
TAP Air Portugal