TAP Air Portugal is selling cheap flights from Chicago, United States to Milan, Italy for as low as $329 return! That works out to a cost of just 3.6 Cents Per Mile for this 9000 mile journey.

The fare only includes carry-on luggage, so you need to pay extra if you want to check bags.

Our data shows the lowest prices are available in February 2022. See the link(s) below for dates and prices.

Sample date(s) with Kiwi.com booking link

Jan 18 – Jan 25 ($338)


Feb 1 – Feb 15 ($338)


Feb 3 – Feb 12 ($337)


Feb 4 – Feb 12 ($338)


Feb 4 – Feb 15 ($329)


Feb 4 – Feb 17 ($338)


Feb 4 – Feb 25 ($338)


Feb 6 – Feb 15 ($329)


Feb 6 – Feb 18 ($338)


Feb 6 – Feb 22 ($338)

Are you looking for an apartment to rent for your stay in Milan, Italy? Check out what Vrbo.com has to offer!

We post many cheap flights like this one from Chicago, United States to Milan, Italy every single day, so have a look at our Travel Deals page, or check out the related posts below!

Note: Prices are valid at the time of publishing this post, but may change in the future.

COVID-19 Note: During these uncertain times, please make sure to check the relevant Coronavirus restrictions for your destination before you book and before you fly. We recommend also checking the refund policy of the airline, as well as purchasing travel insurance for your trip.