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Find the Cheapest Flights from Chicago to Italy

Unlock the cheapest flights and the best airfares from Chicago to Italy. Make your dream trip both memorable and affordable!

Airline Passaredo Linhas Aereas icon
Mon, May 25CHI-ROM
Passaredo Linhas Aereas
oneway$356
Airline Porter Airlines icon
Mon, Jun 15CHI-MIL
Porter Airlines
oneway$363
Airline Porter Airlines icon
Wed, May 27CHI-CTA
Porter Airlines
oneway$422
Airline Porter Airlines icon
Tue, Jun 16CHI-VRN
Porter Airlines
oneway$425

Chicago to Italy: Flight information

Cheapest flight found$356
Cheapest month to flyMay
Most popular airlinePassaredo Linhas Aereas
Average flight duration1d 5h 50m

Cheapest flight found

May 2026

$356

Jun 2026

$380

Dec 2026

$434

FAQs

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