TAP Air Portugal is selling cheap flights from Madrid, Spain to Chicago, United States for as low as €243 return! That works out to a cost of just 2.9 (Euro) Cents Per Mile for this 8400 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

Sep 1 – Sep 8 (€261)


Sep 3 – Sep 10 (€261)


Sep 3 – Sep 11 (€261)


Sep 4 – Sep 10 (€261)


Sep 17 – Sep 24 (€261)


Sep 19 – Sep 26 (€261)


Sep 20 – Sep 26 (€261)


Sep 22 – Sep 29 (€261)


Nov 19 – Nov 26 (€247)


Feb 6 – Feb 20 (€243)

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

We post many cheap flights like this one from Madrid, Spain to Chicago, United States 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.