App
Customer Support
EUR
Find Bookings
Trip.com
>
Cheap Flights
>
Greece
>
Thessaly
>
Skiathos
>
Flights from Chicago to Skiathos
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Flights from Chicago to Skiathos Starting at €528

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • ORD21:15
        27h 40m
        2 stops
        JSI07:55
        Mon, Mar 17|Chicago - Skiathos|American Airlines
        €528€785
        33% OFF
        33% OFF
        €785€528

        Choose American Airlines flights from Chicago to Skiathos. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Mon, Mar 17, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €528 including taxes and charges.

      • ORD18:26
        29h 29m
        2 stops
        JSI07:55
        Fri, Feb 28|Chicago - Skiathos|American Airlines
        €558€785
        28% OFF
        28% OFF
        €785€558

        Choose American Airlines flights from Chicago to Skiathos. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Fri, Feb 28, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €558 including taxes and charges.

      • ORD18:00
        29h 55m
        2 stops
        JSI07:55
        Fri, Feb 28|Chicago - Skiathos|United Airlines
        €565€785
        28% OFF
        28% OFF
        €785€565

        Choose United Airlines flights from Chicago to Skiathos. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Feb 28, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €565 including taxes and charges.

      • ORD22:55
        34h 45m
        2 stops
        JSI16:40
        Wed, Mar 19|Chicago - Skiathos|LOT Polish Airlines
        €571
        €571

        Choose LOT Polish Airlines flights from Chicago to Skiathos. The one-way connecting flight with LOT Polish Airlines departs from O'Hare International Airport on Wed, Mar 19, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €571 including taxes and charges.

      • ORD19:00
        38h 40m
        2 stops
        JSI16:40
        Wed, Mar 19|Chicago - Skiathos|United Airlines
        €572
        €572

        Choose United Airlines flights from Chicago to Skiathos. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Wed, Mar 19, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €572 including taxes and charges.

      • ORD21:55
        26h
        2 stops
        JSI07:55
        Fri, Feb 28|Chicago - Skiathos|LOT Polish Airlines
        €581
        €581

        Choose LOT Polish Airlines flights from Chicago to Skiathos. The one-way connecting flight with LOT Polish Airlines departs from O'Hare International Airport on Fri, Feb 28, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €581 including taxes and charges.

      • ORD11:55
        20h 45m
        2 stops
        JSI16:40
        Thu, Mar 6|Chicago - Skiathos|Turkish Airlines
        €583
        €583

        Choose Turkish Airlines flights from Chicago to Skiathos. The one-way connecting flight with Turkish Airlines departs from O'Hare International Airport on Thu, Mar 6, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €583 including taxes and charges.

      • ORD16:10
        16h 30m
        2 stops
        JSI16:40
        Thu, Mar 6|Chicago - Skiathos|United Airlines
        €586
        €586

        Choose United Airlines flights from Chicago to Skiathos. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Thu, Mar 6, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €586 including taxes and charges.

      • ORD21:25
        26h 30m
        2 stops
        JSI07:55
        Fri, Feb 28|Chicago - Skiathos|Lufthansa
        €589
        €589

        Choose Lufthansa flights from Chicago to Skiathos. The one-way connecting flight with Lufthansa departs from O'Hare International Airport on Fri, Feb 28, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €589 including taxes and charges.

      • ORD16:20
        31h 35m
        2 stops
        JSI07:55
        Fri, Feb 28|Chicago - Skiathos|Austrian Airlines
        €595
        €595

        Choose Austrian Airlines flights from Chicago to Skiathos. The one-way connecting flight with Austrian Airlines departs from O'Hare International Airport on Fri, Feb 28, arriving at Alexandros Papadiamantis Airport. One-way Prices start from €595 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        JSI02:00 pm
        Sat, Feb 22|Chicago - Skiathos|American Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Chicago to Skiathos flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. TK186

    Turkish Airlines

    11:25

    ORD

    10.3h

    05:45

    IST

    S-TW-FS
    Search

  2. TK1843

    Turkish Airlines

    07:30

    IST

    1.5h

    09:00

    ATH

    SMTWTFS

  3. GQ430

    SKY express

    16:00

    ATH

    0.7h

    16:40

    JSI

    S---T--

  4. UA003

    United Airlines

    16:10

    ORD

    9.8h

    07:55

    ZRH

    ---W---
    Search

  5. UA9756

    United Airlines

    09:15

    ZRH

    2.7h

    12:55

    ATH

    ---WT-S

  6. GQ430

    SKY express

    16:00

    ATH

    0.7h

    16:40

    JSI

    S---T--

  7. LH431

    Lufthansa

    16:55

    ORD

    8.5h

    07:25

    FRA

    SMTWTFS
    Search

  8. LH1278

    Lufthansa

    07:00

    FRA

    2.8h

    10:50

    ATH

    SMTWTFS

  9. GQ430

    SKY express

    16:00

    ATH

    0.7h

    16:40

    JSI

    S---T--

  10. LX009

    Swiss Airlines

    19:05

    ORD

    8.7h

    10:45

    ZRH

    SMTWTFS
    Search

  11. LX1842

    Swiss Airlines

    21:00

    ZRH

    2.6h

    00:35

    ATH

    SMTWTFS

  12. A37090

    Aegean Airlines

    07:10

    ATH

    0.8h

    07:55

    JSI

    --T---S

  13. AA086

    American Airlines

    19:25

    ORD

    7.8h

    08:15

    LHR

    SMTWTFS
    Search

  14. A3603

    Aegean Airlines

    16:35

    LHR

    3.8h

    22:20

    ATH

    SMTWTFS

  15. A37090

    Aegean Airlines

    07:10

    ATH

    0.8h

    07:55

    JSI

    --T---S

  16. TK006

    Turkish Airlines

    21:20

    ORD

    10.7h

    16:00

    IST

    SMTWTFS
    Search

  17. TK1845

    Turkish Airlines

    18:55

    IST

    1.6h

    20:30

    ATH

    SMTWTFS

  18. A37090

    Aegean Airlines

    07:10

    ATH

    0.8h

    07:55

    JSI

    --T---S

  19. LH435

    Lufthansa

    22:25

    ORD

    8.3h

    12:45

    MUC

    S-TWTFS
    Search

  20. LH1756

    Lufthansa

    19:30

    MUC

    2.5h

    23:00

    ATH

    SMTWTFS

  21. A37090

    Aegean Airlines

    07:10

    ATH

    0.8h

    07:55

    JSI

    --T---S

  22. LH435

    Lufthansa

    22:25

    ORD

    8.3h

    12:45

    MUC

    S-TWTFS
    Search

  23. LH1754

    Lufthansa

    15:05

    MUC

    2.5h

    18:35

    ATH

    ----TFS

  24. A37090

    Aegean Airlines

    07:10

    ATH

    0.8h

    07:55

    JSI

    --T---S

  25. LO004

    LOT Polish Airlines

    22:55

    ORD

    8.9h

    13:50

    WAW

    SMTWTF-
    Search

  26. LO603

    LOT Polish Airlines

    15:00

    WAW

    2.7h

    18:40

    ATH

    SM-W-F-

  27. A37090

    Aegean Airlines

    07:10

    ATH

    0.8h

    07:55

    JSI

    --T---S

  28. AA090

    American Airlines

    23:00

    ORD

    7.7h

    11:40

    LHR

    SMTWTFS
    Search

  29. A3605

    Aegean Airlines

    19:00

    LHR

    3.6h

    00:35

    ATH

    SMTWT-S

  30. A37090

    Aegean Airlines

    07:10

    ATH

    0.8h

    07:55

    JSI

    --T---S
Find more flights and airlines

Find the best time to fly from Chicago to Skiathos

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

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 Skiathos (JSI) the cheapest?

    Airlines adjust prices for flights from Chicago to Skiathos based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Skiathos (JSI) cost?

    According to Trip.com's data, the lowest price is around €1,352.

  • What is the transportation method from the main airport to downtown in Skiathos?

    • The distance from Alexandros Papadiamantis Airport to downtown is about 1 km. It takes about 20 minutes by taxi.

How to find a cheap flight from Chicago to Skiathos

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 Skiathos. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Skiathos

Off-season for travelJanuary
Peak season for travelDecember
Flight distance8,636.96 km
Popular airlineLufthansa

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.