Cheap Flights from Chicago to Thessaly from 1.011 € Return

Flight deals from Chicago to Thessaly

Looking for a cheap last-minute deal or the best return flight from Chicago to Thessaly? If you want to travel next month, return fares start from 1.011 €. Find the lowest prices on one-way and return tickets right here.

Skiathos.1.011 € per passenger.Departing Sat, 20 Jun, returning Fri, 26 Jun.Return flight with Porter Airlines and Ryanair.Outbound indirect flight with Porter Airlines, departs from Chicago Midway on Sat, 20 Jun, arriving in Skiathos Island National.Inbound indirect flight with Ryanair, departs from Skiathos Island National on Fri, 26 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 1.011 €, select.

Volos.1.088 € per passenger.Departing Fri, 3 Jul, returning Fri, 10 Jul.Return flight with Allegiant Air and Ryanair.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Fri, 3 Jul, arriving in Volos.Inbound indirect flight with Ryanair, departs from Volos on Fri, 10 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 1.088 €, select.

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Flying from Chicago to Thessaly

Arm yourself with these facts on the fly.

Cheapest flight found	1.011 €
Cheapest month to fly	June
Cheapest airport to fly from	Chicago Midway

How to find cheap flights from Chicago to Thessaly

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Thessaly. Other savvy travellers recently found return flights from 1.011 € and one-way tickets from 344 € one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago Midway into Skiathos Island National

At the moment, the lowest priced flight tickets to Thessaly are from Chicago Midway Airport to Skiathos Island National Airport.

Fly in June

We crunched the flight calendar and found the cheapest time to fly from Chicago to Thessaly is currently June.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Thessaly.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Thessaly go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Thessaly to Thessaly flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Thessaly flight price?

We looked at all of the upcoming return flights from Chicago to Thessaly we could find over the next 12 months. It looks like 1.011 € is the best price. This is good, compared to the average Thessaly ticket price of 1.050 €.

What is the cheapest month to fly from Chicago to Thessaly?

The cheapest month to fly from Chicago to Skiathos Island National Airport is currently June. The cheapest month to fly from Chicago to Volos Airport is usually July

Which upcoming date is cheapest to fly from Chicago to Thessaly on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Thessaly on Saturday, 20 June 2026.

Are there any direct flights from Chicago to Thessaly?

Currently, there aren't any direct flights from Chicago to Thessaly, but you can still fly with a stopover.

If I'm flying from Chicago, where in Thessaly is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Thessaly to fly into is Skiathos. The cheapest airport serving Skiathos at the moment is Skiathos Island National.