$516 Cheap Flights from Chicago (ORD) to Skiathos (JSI)

View $516 flight on Wed, Aug 13, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Skiathos (ORD-JSI)

Prices were available within the past 7 days and start at $516 for one-way flights and $757 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Mon, Aug 18 - Tue, Aug 26
ORD
Chicago
JSI
Skiathos
$757 Roundtrip, found 3 days ago
$757
Roundtrip
found 3 days ago
Select United flight, departing Mon, Aug 18 from Chicago to Skiathos, returning Tue, Aug 26, priced at $757 found 3 days ago
United
Mon, Aug 18 - Fri, Aug 29
ORD
Chicago
JSI
Skiathos
$796 Roundtrip, found 6 days ago
$796
Roundtrip
found 6 days ago
Select United flight, departing Mon, Aug 18 from Chicago to Skiathos, returning Fri, Aug 29, priced at $796 found 6 days ago
Lufthansa
Sun, Aug 17 - Tue, Aug 26
ORD
Chicago
JSI
Skiathos
$847 Roundtrip, found 6 days ago
$847
Roundtrip
found 6 days ago
Select Lufthansa flight, departing Sun, Aug 17 from Chicago to Skiathos, returning Tue, Aug 26, priced at $847 found 6 days ago
Swiss International Air Lines
Thu, Aug 21 - Tue, Aug 26
ORD
Chicago
JSI
Skiathos
$848 Roundtrip, found 6 days ago
$848
Roundtrip
found 6 days ago
Select Swiss International Air Lines flight, departing Thu, Aug 21 from Chicago to Skiathos, returning Tue, Aug 26, priced at $848 found 6 days ago
Swiss International Air Lines
Thu, Aug 14 - Fri, Aug 22
ORD
Chicago
JSI
Skiathos
$861 Roundtrip, found 3 days ago
$861
Roundtrip
found 3 days ago
Select Swiss International Air Lines flight, departing Thu, Aug 14 from Chicago to Skiathos, returning Fri, Aug 22, priced at $861 found 3 days ago
Swiss International Air Lines
Thu, Aug 14 - Tue, Aug 26
ORD
Chicago
JSI
Skiathos
$863 Roundtrip, found 3 days ago
$863
Roundtrip
found 3 days ago
Select Swiss International Air Lines flight, departing Thu, Aug 14 from Chicago to Skiathos, returning Tue, Aug 26, priced at $863 found 3 days ago
Lufthansa
Sun, Aug 17 - Tue, Aug 26
ORD
Chicago
JSI
Skiathos
$871 Roundtrip, found 3 days ago
$871
Roundtrip
found 3 days ago
Select Lufthansa flight, departing Sun, Aug 17 from Chicago to Skiathos, returning Tue, Aug 26, priced at $871 found 3 days ago
Austrian Airlines
Wed, Sep 17 - Wed, Sep 24
ORD
Chicago
JSI
Skiathos
$885 Roundtrip, found 2 days ago
$885
Roundtrip
found 2 days ago
Select Austrian Airlines flight, departing Wed, Sep 17 from Chicago to Skiathos, returning Wed, Sep 24, priced at $885 found 2 days ago
Lufthansa
Wed, Aug 13 - Fri, Aug 22
ORD
Chicago
JSI
Skiathos
$906 Roundtrip, found 3 days ago
$906
Roundtrip
found 3 days ago
Select Lufthansa flight, departing Wed, Aug 13 from Chicago to Skiathos, returning Fri, Aug 22, priced at $906 found 3 days ago
Air Canada
Sun, Aug 17 - Fri, Sep 5
ORD
Chicago
JSI
Skiathos
$967 Roundtrip, found 6 days ago
$967
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Aug 17 from Chicago to Skiathos, returning Fri, Sep 5, priced at $967 found 6 days ago

Alternative airports near Skiathos

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Skiathos Island National JSI. Cheapest and Closest option available. Average driving time to city center is 4 minutes. Flights from $1,252
JSI
Skiathos Island National
CheapestClosest
Average driving time to city center4 min
Flights from $1,252
Flights from Chicago (ORD) to Skiathos (JSI)
Origin airport
O'Hare Intl.
Destination airport
Skiathos Island National
Airlines serving
British Airways, Lufthansa
Roundtrip price
$756
Distance
5371 mi

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 August. 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 $516 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.

 

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 $516 or cheap return flight from $757 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)?
August 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.

Explore a world of travel with Expedia

*Available to One Key members.