Chicago to Milan, Italy for only $376 roundtrip

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

DEPART:
Chicago, USA

ARRIVE:
Milan, Italy

RETURN:
Chicago, USA

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

Example dates:
2nd-9th Nov
5th-12th Nov
7th-14th Nov
9th-16th Nov
12th-19th Nov
14th-21st Nov
16th-23rd Nov
30th Nov – 7th Dec
3rd-10th Dec
7th-14th Dec
10th-17th Dec
7th-14th Jan
9th-16th Jan
14th-21st Jan
18th-25th Jan
21st-28th Jan
25th Jan – 1st Feb
28th Jan – 4th Feb
1st-8th Feb
4th-11th Feb
8th-15th Feb
11th-18th Feb
1st-8th Mar
4th-11th Mar
8th-15th Mar
11th-18th Mar

and more…

STOPS:
Lisbon

AIRLINES:
TAP Air Portugal