$606 Cheap Flights from Chicago (ORD) to Ermoupolis (JSY)

View $606 flight on Mon, Nov 10, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Ermoupolis (JSY-Syros Island National)

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Cheap Flights from Chicago to Ermoupolis (ORD-JSY)

Prices were available within the past 7 days and start at $606 for one-way flights and $907 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air France
Mon, Dec 8 - Mon, Jan 12
ORD
Chicago
JSY
Ermoupoli
$907 Roundtrip, found 6 days ago
$907
Roundtrip
found 6 days ago
Select Air France flight, departing Mon, Dec 8 from Chicago to Ermoupoli, returning Mon, Jan 12, priced at $907 found 6 days ago
KLM
Wed, Dec 10 - Mon, Jan 12
ORD
Chicago
JSY
Ermoupoli
$912 Roundtrip, found 6 days ago
$912
Roundtrip
found 6 days ago
Select KLM flight, departing Wed, Dec 10 from Chicago to Ermoupoli, returning Mon, Jan 12, priced at $912 found 6 days ago
Air France
Mon, Dec 8 - Fri, Jan 16
ORD
Chicago
JSY
Ermoupoli
$938 Roundtrip, found 6 days ago
$938
Roundtrip
found 6 days ago
Select Air France flight, departing Mon, Dec 8 from Chicago to Ermoupoli, returning Fri, Jan 16, priced at $938 found 6 days ago
KLM
Wed, Dec 10 - Fri, Jan 16
ORD
Chicago
JSY
Ermoupoli
$944 Roundtrip, found 6 days ago
$944
Roundtrip
found 6 days ago
Select KLM flight, departing Wed, Dec 10 from Chicago to Ermoupoli, returning Fri, Jan 16, priced at $944 found 6 days ago
Delta
Thu, Dec 11 - Mon, Jan 12
ORD
Chicago
JSY
Ermoupoli
$1,056 Roundtrip, found 6 days ago
$1,056
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 11 from Chicago to Ermoupoli, returning Mon, Jan 12, priced at $1,056 found 6 days ago
Delta
Thu, Dec 11 - Fri, Jan 16
ORD
Chicago
JSY
Ermoupoli
$1,088 Roundtrip, found 6 days ago
$1,088
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 11 from Chicago to Ermoupoli, returning Fri, Jan 16, priced at $1,088 found 6 days ago
LOT-Polish Airlines
Mon, Dec 8 - Wed, Jan 14
ORD
Chicago
JSY
Ermoupoli
$1,169 Roundtrip, found 6 days ago
$1,169
Roundtrip
found 6 days ago
Select LOT-Polish Airlines flight, departing Mon, Dec 8 from Chicago to Ermoupoli, returning Wed, Jan 14, priced at $1,169 found 6 days ago
KLM
Sat, Dec 13 - Mon, Jan 12
ORD
Chicago
JSY
Ermoupoli
$1,337 Roundtrip, found 6 days ago
$1,337
Roundtrip
found 6 days ago
Select KLM flight, departing Sat, Dec 13 from Chicago to Ermoupoli, returning Mon, Jan 12, priced at $1,337 found 6 days ago
KLM
Sat, Dec 13 - Fri, Jan 16
ORD
Chicago
JSY
Ermoupoli
$1,369 Roundtrip, found 6 days ago
$1,369
Roundtrip
found 6 days ago
Select KLM flight, departing Sat, Dec 13 from Chicago to Ermoupoli, returning Fri, Jan 16, priced at $1,369 found 6 days ago
Delta
Wed, Jul 22 - Wed, Jul 29
ORD
Chicago
JSY
Ermoupoli
$1,697 Roundtrip, found 6 days ago
$1,697
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jul 22 from Chicago to Ermoupoli, returning Wed, Jul 29, priced at $1,697 found 6 days ago

Alternative airports near Ermoupoli

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

Select flight to Mykonos Island National JMK. Cheapest option available. Average driving time to city center is 5 hours 54 minutes. Flights from $1,018
JMK
Mykonos Island National
Cheapest
Average driving time to city center5 h 54 min
Flights from $1,018

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Syros Island National Airport (JSY) cost?
Get a cheap one-way flight from $606 or cheap return flight from $907 from O'Hare Intl. Airport (ORD) to Syros Island National Airport (JSY) 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 Syros Island National Airport (JSY)?
Planning your trip for December is a great way to save, as it's the cheapest month for flights between ORD and JSY. You'll usually find the lowest prices during the off-season.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Syros Island National Airport (JSY)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from ORD to JSY. Then, sort your results by "Price (lowest to highest)" to pick up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Syros Island National Airport (JSY)?
Direct flights from O'Hare Intl. Airport (ORD) to Syros Island National Airport (JSY) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORD to JSY?
Typically you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* But this can vary depending on the time of year, carrier 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 Syros Island National Airport (JSY)?
Opt for a flight from O'Hare Intl. Airport (ORD) to Syros Island National Airport (JSY) that leaves before 3 PM to reduce the likelihood of delays and cancellations. Later departures are on average 22% more likely to be canceled.**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 Syros Island National Airport (JSY) last-minute?
Waiting until just before your departure to book a flight from ORD to JSY generally means paying more. While you may come across some last-minute offers, there's no guarantee. Keep your travel schedule open to boost your chances of scoring a bargain.
Is it cheaper to book an ORD to JSY flight and hotel package?
Opting for an ORD to JSY flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our wide range of accommodations and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Syros Island National Airport (JSY)?
If you reserved your ORD to JSY flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Syros Island National
Roundtrip price
$906
Distance
5513 mi

Book with confidence

Chicago to Ermoupolis Flights

The cheapest times to fly from Chicago to Ermoupolis

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 Ermoupolis are during the month of December. You can find some of the cheapest flights from Chicago to Ermoupolis with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Ermoupolis

Sunday is one of the best days to book for cheap flights from Chicago to Ermoupolis: 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 Ermoupolis

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 Ermoupolis in 2025. You can also book with separate airlines for your outbound and return journeys, from $606 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 Ermoupolis 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 Ermoupolis 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 Ermoupolis Flights

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