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Greek Islands

$268+ Cheap flights from Chicago (CHI) to Greek Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HER
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap flight deals from Chicago to Greek Islands

Cheapest flights from Chicago to Greek Islands
Explore the most affordable flight options available from Chicago to Greek Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2026.

This oojo deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:15 pm
ORD
-
CHQ
1 stop17h 40m
Scandinavian Airlines
Sun 5/311:25 am
CHQ
-
ORD
1 stop36h 45m
Scandinavian Airlines
Deal found 2/18$532
This Mytrip deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 pm
ORD
-
CHQ
3 stops18h 40m
Multiple Airlines
Mon 4/209:10 pm
CHQ
-
ORD
2 stops28h 40m
Multiple Airlines
Deal found 2/18$686
This Trip.com deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:20 pm
ORD
-
KGS
1 stop20h 30m
Multiple Airlines
Tue 9/88:30 pm
KGS
-
ORD
1 stop27h 25m
Multiple Airlines
Deal found 2/16$703
This Vliegwinkel deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/511:25 am
ORD
-
HER
2 stops22h 50m
Multiple Airlines
Sun 4/1210:25 pm
HER
-
ORD
2 stops19h 15m
Multiple Airlines
Deal found 2/19$725
This Scandinavian Airlines deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:15 pm
ORD
-
CHQ
1 stop18h 15m
Scandinavian Airlines
Thu 10/110:20 pm
CHQ
-
ORD
1 stop25h 50m
Scandinavian Airlines
Deal found 2/16$730
This Kiwi.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:12 pm
ORD
-
KGS
2 stops23h 38m
Austrian Airlines
Mon 9/78:50 pm
KGS
-
ORD
1 stop24h 30m
Austrian Airlines
Deal found 2/18$741
This Trip.com deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:20 pm
ORD
-
KGS
1 stop17h 35m
Multiple Airlines
Mon 9/711:00 am
KGS
-
ORD
1 stop36h 55m
Multiple Airlines
Deal found 2/17$755
This Kiwi.com deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:20 pm
ORD
-
KGS
1 stop17h 35m
Austrian Airlines
Mon 9/78:50 pm
KGS
-
ORD
1 stop24h 30m
Austrian Airlines
Deal found 2/18$756
This Mytrip deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:15 pm
ORD
-
CHQ
2 stops18h 50m
Multiple Airlines
Sun 5/33:00 pm
CHQ
-
ORD
2 stops33h 10m
Multiple Airlines
Deal found 2/17$760
This KAYAK deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 pm
ORD
-
CFU
1 stop13h 45m
Multiple Airlines
Mon 8/313:35 pm
CFU
-
ORD
1 stop32h 20m
Multiple Airlines
Deal found 2/19$770
This Expedia deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:05 pm
ORD
-
KGS
1 stop31h 05m
SWISS
Mon 9/711:00 am
KGS
-
ORD
1 stop36h 55m
SWISS
Deal found 2/17$772
This Kiwi.com deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:25 pm
ORD
-
CFU
2 stops18h 00m
Multiple Airlines
Sun 10/45:45 am
CFU
-
ORD
1 stop14h 05m
Multiple Airlines
Deal found 2/20$772

Find flight deals from Chicago to Greek Islands

Keep the following information in mind while searching for Chicago to Greek Islands flight deals. Data was last updated February 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$532
(oojo)

One-way from

$268
(Kiwi.com)
Provider with most accurate pricing for Chicago (CHI)-Thera Santorini flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Thera Santorini flights.
Search Deals
From Chicago (CHI) to Greek Islands
Search Deals
One-way flight from Chicago (CHI) to Greek Islands
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Greek Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2026.
Use the filters below to find and compare flights from Chicago to Greek Islands that are best for you.

Fly from

Chicago

Fly to

Greek Islands

Route

Depart

Return

Price

ChicagoChania

ORD - CHQ

ORDCHQ

Chicago O'Hare Intl

Mon 4/20

7:15 pm-8:55 pm

1 stop17h 40m

Chania Souda

Sun 5/3

11:25 am-4:10 pm

1 stop36h 45m

$532

ChicagoChania

ORD - CHQ

ORDCHQ

Chicago O'Hare Intl

Sun 4/12

7:25 pm-10:05 pm

3 stops18h 40m

Chania Souda

Mon 4/20

9:10 pm-5:50 pm

2 stops28h 40m

$686

ChicagoHeraklion

ORD - HER

ORDHER

Chicago O'Hare Intl

Sun 4/5

11:25 am-6:15 pm

2 stops22h 50m

Heraklion N. Kazantzakis Apt.

Sun 4/12

10:25 pm-9:40 am

2 stops19h 15m

$725

ChicagoChania

ORD - CHQ

ORDCHQ

Chicago O'Hare Intl

Mon 4/20

7:15 pm-10:05 pm

2 stops18h 50m

Chania Souda

Sun 5/3

3:00 pm-4:10 pm

2 stops33h 10m

$760

ChicagoMykonos

ORD - JMK

ORDJMK

Chicago O'Hare Intl

Mon 8/17

9:15 pm-4:50 pm

1 stop35h 35m

Mikonos

Mon 8/31

4:00 pm-1:50 pm

1 stop29h 50m

$773

ChicagoHeraklion

ORD - HER

ORDHER

Chicago O'Hare Intl

Sun 4/12

7:25 pm-9:45 pm

3 stops18h 20m

Heraklion N. Kazantzakis Apt.

Mon 4/20

9:50 pm-5:50 pm

2 stops28h 00m

$816

ChicagoThera

ORD - JTR

ORDJTR

Chicago O'Hare Intl

Mon 5/4

7:15 pm-12:15 am

2 stops21h 00m

Thera Santorini

Fri 5/8

6:00 am-4:10 pm

2 stops42h 10m

$822

ChicagoArgostoli

ORD - EFL

ORDEFL

Chicago O'Hare Intl

Sat 8/15

9:15 pm-5:15 pm

2 stops36h 00m

Argostoli Cephalonia

Sat 9/5

7:20 pm-12:35 pm

1 stop25h 15m

$830

ChicagoArgostoli

ORD - EFL

ORDEFL

Chicago O'Hare Intl

Sat 8/15

3:00 pm-5:40 pm

1 stop18h 40m

Argostoli Cephalonia

Sat 9/5

8:10 pm-1:10 pm

1 stop25h 00m

$832

ChicagoRhodes

ORD - RHO

ORDRHO

Chicago O'Hare Intl

Sat 4/4

7:25 pm-9:20 pm

2 stops17h 55m

Rhodes Diagoras

Sat 4/11

10:10 pm-5:50 pm

3 stops27h 40m

$839

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 53 results
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Best time to book a flight from Chicago to Greek Islands

Have a flexible travel schedule? Discover the best time to fly to Greek Islands from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Greek Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Greek Islands

Get insights into the airlines that provide service to Greek Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Greek Islands. Reviews last updated February 20, 2026.
Peruse reviews from past customers who have flown with Finnair, SWISS, and Lufthansa from Chicago to Greek Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Finnair
7.6
Good
1,364 reviews

Entertainment

6.9

Food

6.7

Overall

7.6

Boarding

7.7

Crew

8.2

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
Finnair
7.6
Good
1,364 reviews
Finnair
7.6
Good
1,364 reviews

Entertainment

6.9

Food

6.7

Overall

7.6

Boarding

7.7

Crew

8.2

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
SWISS
7.5
Good
1,878 reviews
Finnair
7.6
Good
1,364 reviews

Entertainment

6.9

Food

6.7

Overall

7.6

Boarding

7.7

Crew

8.2

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
Lufthansa
6.8
Okay
7,789 reviews
Finnair
7.6
Good
1,364 reviews

Entertainment

6.9

Food

6.7

Overall

7.6

Boarding

7.7

Crew

8.2

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.
British Airways
6.7
Okay
7,756 reviews
Finnair
7.6
Good
1,364 reviews

Entertainment

6.9

Food

6.7

Overall

7.6

Boarding

7.7

Crew

8.2

Comfort

7.4

Reviews

1 / 20
4.0
Okay

Anonymous,Sep 2025

WAW - HEL

My flight to Europe was cancelled and rebooked. Bags got lost by FinnAir. Flight back home from Europe was cancelled the very next day after we landed. Zero compensation for these back to back cancellations on the exact same trip. Kayak doesn’t help with flight cancellation before trips says to contact trip protection only for trip protection to say it’s up to kayak. Don’t fly FinnAir.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Greek Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Greek Islands?

    Airlines like Scandinavian Airlines, British Airways, and ITA Airways fly from Chicago to Greek Islands in about 17h 40m. The time it takes to get you to your destination can typically vary by up to 17h 55m. The distance from Chicago to Greek Islands is about 5572 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago to Greek Islands?

    The most popular route from Chicago to Greek Islands is Chicago O'Hare Intl - Corfu Ioannis Kapodistrias. You may also consider Chicago O'Hare Intl - Thera Santorini or Chicago O'Hare Intl - Chania Souda.

  • Can I find deals for flights from Chicago to Greek Islands that include hotel bookings?

    Yes. In addition to deals on Chicago to Greek Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Greek Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Greek Islands.

  • Can I find deals for business class flights from Chicago to Greek Islands?

    Yes. Cheapflights offers flight deals from Chicago to Greek Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top 3 airlines flying from Chicago to Greek Islands

Discover the top 3 airlines that operate flights from Chicago to Greek Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
SWISSCheapest$572Average$997FlexibilityNo cancel feeOn-time79%
British AirwaysCheapest$602Average$1,024FlexibilityNo cancel feeOn-time70%
LufthansaCheapest$842Average$1,204FlexibilityNo cancel feeOn-time76%

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