US cities to Italian cities from only $314 roundtrip

Missed the deal?

Become a Secret Flying member to receive alerts to your inbox the moment we publish a flight deal.

You'll never miss a Secret Flying deal again.

Cheap flights from US cities to Italian cities from only $314 roundtrip with TAP Air Portugal.

Routes:
New York – Rome: $314-$322
Boston – Rome: $324
New York – Bologna: $331-$362
New York – Florence: $331-$360
New York – Venice: $333-$351
Boston – Bologna: $344-$369
Boston – Venice: $349-$365
Boston – Florence: $352-$366
Boston – Milan: $357-$371
New York – Milan: $357-$359
Miami – Rome: $364
Chicago – Bologna: $366
Washington DC – Bologna: $366
Chicago – Milan: $371
Washington DC – Milan: $371-$373
Chicago – Rome: $383
Washington DC – Rome: $383

DEPART:
New York/Boston/Miami/Chicago/Washington DC, USA

ARRIVE:
Rome/Bologna/Florence/Venice/Milan, Italy

RETURN:
New York/Boston/Miami/Chicago/Washington DC, USA

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

Example dates:

New York – Rome: $314-$322
13th-23rd Jan
21st-31st Jan
29th Jan – 8th Feb
14th-24th Feb
22nd Feb – 4th Mar
2nd-12th Mar

Boston – Rome: $324
10th-20th Nov
26th Nov – 6th Dec
4th-14th Dec
6th-16th Feb

New York – Bologna: $331-$362
25th Oct – 4th Nov
2nd-12th Nov
10th-20th Nov
13th-23rd Jan
21st-31st Jan
29th Jan – 8th Feb
2nd-12th Mar
10th-20th Mar

New York – Florence: $331-$360
2nd-12th Nov
10th-20th Nov
13th-23rd Jan
29th Jan – 8th Feb
6th-16th Feb
14th-24th Feb
22nd Feb – 4th Mar
2nd-12th Mar
10th-20th Mar

New York – Venice: $333-$351
10th-20th Nov
13th-23rd Jan
21st-31st Jan
29th Jan – 8th Feb
14th-24th Feb
22nd Feb – 4th Mar
2nd-12th Mar

Boston – Bologna: $344-$369
2nd-12th Nov
10th-20th Nov
5th-15th Jan
13th-23rd Jan
22nd Feb – 4th Mar
2nd-12th Mar
10th-20th Mar

Boston – Venice: $349-$365
10th-20th Nov
5th-15th Jan
13th-23rd Jan
22nd Feb – 4th Mar
2nd-12th Mar

Boston – Florence: $352-$366
2nd-12th Nov
10th-20th Nov
22nd Feb – 4th Mar
2nd-12th Mar
10th-20th Mar

Boston – Milan: $357-$371
25th Oct – 4th Nov
10th-20th Nov
18th-28th Nov
4th-14th Dec
29th Jan – 8th Feb
14th-24th Feb
10th-20th Mar

New York – Milan: $357-$359
2nd-12th Nov
18th-28th Nov
21st-31st Jan

Miami – Rome: $364
26th Nov – 6th Dec
29th Jan – 8th Feb

Chicago – Bologna: $366
10th-20th Nov

Washington DC – Bologna: $366
4th-14th Dec
29th Jan – 8th Feb

Chicago – Milan: $371
10th-20th Nov
4th-14th Dec
21st-31st Jan
29th Jan – 8th Feb
22nd Feb – 4th Mar
2nd-12th Mar

Washington DC – Milan: $371-$373
4th-14th Dec
13th-23rd Jan
21st-31st Jan
29th Jan – 8th Feb
14th-24th Feb
22nd Feb – 4th Mar
2nd-12th Mar
18th-28th Mar

Chicago – Rome: $383
10th-20th Nov
26th Nov – 6th Dec
21st-31st Jan
2nd-12th Mar

Washington DC – Rome: $383
21st-31st Jan
29th Jan – 8th Feb

and more…

STOPS:
Lisbon

AIRLINES:
TAP Air Portugal