$738 Cheap Flights from Chicago (ORD) to Skiathos (JSI)

View $738 flight on Sun, Sep 20, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Skiathos (JSI-Skiathos Island National)

Cheap Flights from Chicago to Skiathos (ORD-JSI)

Prices were available within the past 7 days and start at $738 for one-way flights and $1,223 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

LOT-Polish Airlines
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,223 Roundtrip, found 1 day ago
$1,223
Roundtrip
found 1 day ago
Select LOT-Polish Airlines flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,223 found 1 day ago
LOT-Polish Airlines
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,228 Roundtrip, found 1 day ago
$1,228
Roundtrip
found 1 day ago
Select LOT-Polish Airlines flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,228 found 1 day ago
Air Canada
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,291 Roundtrip, found 1 day ago
$1,291
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,291 found 1 day ago
Air Canada
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,298 Roundtrip, found 1 day ago
$1,298
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,298 found 1 day ago
Air Canada
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,305 Roundtrip, found 1 day ago
$1,305
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,305 found 1 day ago
LOT-Polish Airlines
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,308 Roundtrip, found 1 day ago
$1,308
Roundtrip
found 1 day ago
Select LOT-Polish Airlines flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,308 found 1 day ago
Air Canada
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,311 Roundtrip, found 1 day ago
$1,311
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,311 found 1 day ago
LOT-Polish Airlines
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,313 Roundtrip, found 1 day ago
$1,313
Roundtrip
found 1 day ago
Select LOT-Polish Airlines flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,313 found 1 day ago
Lufthansa
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,382 Roundtrip, found 1 day ago
$1,382
Roundtrip
found 1 day ago
Select Lufthansa flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,382 found 1 day ago
LOT-Polish Airlines
Sun, Sep 20 - Wed, Sep 30
ORD
Chicago
JSI
Skiathos
$1,403 Roundtrip, found 1 day ago
$1,403
Roundtrip
found 1 day ago
Select LOT-Polish Airlines flight, departing Sun, Sep 20 from Chicago to Skiathos, returning Wed, Sep 30, priced at $1,403 found 1 day ago

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI) cost?
Secure a cheap one-way flight from $738 or cheap return flight from $1,223 from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI)?
September is the least expensive month to fly from ORD to JSI. Timing your trip outside of the busy season is often the key to landing a great deal.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI)?
To find the cheapest airline that'll fly you from ORD to JSI, use Expedia's filter tool. Tailor your search based on what's important to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI)?
You'll have to take a flight with a layover when traveling from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI). There are no daily direct flights on this route. However, just filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from ORD to JSI?
Generally you'll find the widest variety of flight choices on a Friday. Tuesdays are often the quietest.* However, this can vary based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI)?
Opt for a flight from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI) last-minute?
Holding off until right before your break to book your flight from ORD to JSI generally means paying more. While you may come across some last-minute offers, they're not always guaranteed. Allow some flexibility in your schedule to maximize your chances of snagging a bargain.
Is it cheaper to book an ORD to JSI flight and hotel package?
You'll generally save money by securing an ORD to JSI flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. Once you've chosen your ideal flights and accommodations, consider adding extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Skiathos Island National Airport (JSI)?
In most cases, you can cancel or modify your ORD to JSI flight. However, additional fees may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you'd like more details, go to our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Skiathos Island National
Roundtrip price
$1,222
Distance
5371 mi

Book with confidence

Chicago to Skiathos Flights

The cheapest times to fly from Chicago to Skiathos

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Skiathos are during the month of September. You can find some of the cheapest flights from Chicago to Skiathos with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Skiathos

Sunday is one of the best days to book for cheap flights from Chicago to Skiathos: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Skiathos

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Skiathos in 2025. You can also book with separate airlines for your outbound and return journeys, from $738 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Skiathos flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Skiathos airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Skiathos Flights

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*Available to One Key members.