Chicago to Madrid or Barcelona, Spain from only $322 roundtrip

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Cheap flights from Chicago to Madrid or Barcelona, Spain from only $322 roundtrip with TAP Air Portugal.

Fly to:
Madrid: $322
Barcelona: $355

DEPART:
Chicago, USA

ARRIVE:
Madrid/Barcelona, Spain

RETURN:
Chicago, USA

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

Example dates:

Chicago – Madrid: $322
5th-12th Nov
14th-21st Nov
16th-23rd Nov
21st-28th Jan
28th Jan – 4th Feb
4th-11th Feb
11th-18th Feb

Chicago – Barcelona: $355
5th-12th Nov
12th-19th Nov
14th-21st Nov
16th-23rd Nov
28th Nov – 5th Dec
5th-12th Dec
14th-21st Jan
21st-28th Jan
28th Jan – 4th Feb
30th Jan – 6th Feb

and more…

STOPS:
Lisbon

AIRLINES:
TAP Air Portugal