Cheap Flights from Chicago to Syros Island starting at RM 2,743

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.

Cheapest time to fly from Chicago to Syros Island

We monitor flight fares to help you find the best deals effortlessly

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 Syros Island (JSY) the cheapest?

Airlines adjust prices for flights from Chicago to Syros Island based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Chicago (CHI) to Syros Island (JSY) cost?

According to Trip.com's data, the lowest price is around RM 5,250.
What is the transportation method from the main airport to downtown in Syros Island?
- The distance from Syros Island Airport to downtown is about 2km, by taxi about 20 minutes.
How many airports in Syros Island (JSY)?

There are 1 airport(s) in Syros Island (JSY): Syros Island Airport.

How to find a cheap flight from Chicago to Syros Island

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 Syros Island. Book your flights at the right time and save more.

Be flexible with your travel dates to get the cheapest flight from Chicago to Syros Island.

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

Compare cheap flight deals from Chicago to Syros Island across hundreds of airlines.

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Don't miss out on cheap flight deals and promo codes from Chicago to Syros Island.

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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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