Find cheap one-way flights from Chicago to Porto Santo starting at US$452.

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

Round-trip
One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to book flights from Chicago to Porto Santo?

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights

From price

23 30
Apr

30 6
6 13
13 20
20 27
May

27 4
4 11
11 18
18 25
Jun

25 1
1 8
8 15

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

When are flight tickets from Chicago (CHI) to Porto Santo (PXO) the cheapest?

Airlines adjust prices for flights from Chicago to Porto Santo based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Chicago (CHI) to Porto Santo (PXO) cost?

According to Trip.com's data, the lowest price is around $1,942.
What is the transportation method from the main airport to downtown in Porto Santo?
- The distance from Porto Santo Airport to downtown is about 1 km. It takes about 20 minutes by taxi.

How to find a cheap flight from Chicago to Porto Santo

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Porto Santo. Book your flights at the right time and save more.

Being flexible with your dates to get the cheapest Chicago to Porto Santo ticket.

Tap "Date" on flight search bar to scan through the calender for Chicago to Porto Santo airfare over next 6 months in 2025.

Compare cheap Chicago to Porto Santo flight deals from over hundreds of airlines.

Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Porto Santo.

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Book early or wait unitl the last minute.

It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.

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