Flights from Chicago to Porto Santo Starting at £350

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

Round-trip
One way

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

Find the best time to fly from Chicago to Porto Santo

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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.

FAQ

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 date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Chicago (CHI) to Porto Santo (PXO) cost?

According to Trip.com's data, the lowest price is around £1,504.
What is the transportation method from the main airport to downtown in Porto Santo?
- The distance from Porto Santo Airport to downtown is about 1km, by taxi about 20 minutes.
How many airports in Porto Santo (PXO)?

There are 1 airport(s) in Porto Santo (PXO): Porto Santo Airport.

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.

Be flexible with your travel dates to get the cheapest flight from Chicago to Porto Santo.

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

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Book early or wait until the last minute.

It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.

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