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Greek Islands

$486+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HER
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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 December 23, 2025.

This Mytrip deal was found by Cheapflights users on 12/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:30 pmORD - HER
3 stops30h 20mMultiple Airlines
Thu 12/2511:35 amHER - ORD
3 stops35h 50mMultiple Airlines
Deal found 12/19$1,639
This Priceline deal was found by Cheapflights users on 12/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:50 pmORD - CFU
2 stops41h 00mMultiple Airlines
Fri 1/28:35 amCFU - ORD
2 stops19h 25mMultiple Airlines
Deal found 12/21$2,711

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 December 23, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$646
(FlightHub)

One-way from

$346
(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.
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From Chicago (CHI) to Greek Islands
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One-way flight from Chicago (CHI) to Greek Islands
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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 December 23, 2025.
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

ChicagoThera

ORD - JTR

ORDJTR

Chicago O'Hare Intl

Wed 1/21

4:05 pm-10:25 pm

2 stops22h 20m

Thera Santorini

Wed 1/28

2:45 pm-1:25 pm

2 stops30h 40m

$646

ChicagoHeraklion

ORD - HER

ORDHER

Chicago O'Hare Intl

Sat 2/28

3:45 pm-4:00 pm

2 stops16h 15m

Heraklion N. Kazantzakis Apt.

Sat 3/7

3:30 pm-11:10 am

1 stop27h 40m

$686

ChicagoHeraklion

ORD - HER

ORDHER

Chicago O'Hare Intl

Wed 2/4

11:50 am-9:05 pm

2 stops25h 15m

Heraklion N. Kazantzakis Apt.

Wed 2/11

9:45 pm-6:25 pm

2 stops28h 40m

$689

ChicagoHeraklion

ORD - HER

ORDHER

Chicago O'Hare Intl

Sat 2/28

3:45 pm-4:00 pm

2 stops16h 15m

Heraklion N. Kazantzakis Apt.

Sat 3/7

9:45 pm-1:25 pm

2 stops23h 40m

$694

ChicagoThera

ORD - JTR

ORDJTR

Chicago O'Hare Intl

Thu 2/5

9:50 pm-7:40 am

2 stops25h 50m

Thera Santorini

Thu 2/12

2:45 pm-1:25 pm

2 stops30h 40m

$773

ChicagoParikia

ORD - PAS

ORDPAS

Chicago O'Hare Intl

Thu 2/5

4:10 pm-4:30 pm

2 stops16h 20m

Parikia Paros

Thu 2/12

8:30 am-6:25 pm

2 stops17h 55m

$791

ChicagoArgostoli

ORD - EFL

ORDEFL

Chicago O'Hare Intl

Fri 1/30

9:50 pm-5:20 pm

2 stops35h 30m

Argostoli Cephalonia

Wed 2/4

2:05 pm-1:25 pm

2 stops55h 20m

$834

ChicagoHeraklion

ORD - HER

ORDHER

Chicago O'Hare Intl

Tue 5/5

4:05 pm-10:25 pm

1 stop22h 20m

Heraklion N. Kazantzakis Apt.

Wed 5/13

9:40 am-7:55 pm

1 stop18h 15m

$836

ChicagoCorfu

ORD - CFU

ORDCFU

Chicago O'Hare Intl

Thu 2/5

9:50 pm-8:00 am

2 stops26h 10m

Corfu Ioannis Kapodistrias

Thu 2/12

8:30 pm-1:10 pm

2 stops24h 40m

$852

ChicagoArgostoli

ORD - EFL

ORDEFL

Chicago O'Hare Intl

Wed 2/4

9:50 pm-5:20 pm

2 stops35h 30m

Argostoli Cephalonia

Wed 2/11

2:05 pm-1:25 pm

2 stops31h 20m

$909

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 42 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

What is the cheapest time of day to fly from CHI to EIO?

Find hourly flight availability from Chicago to Greek Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 32% on flights from Chicago to Greek Islands by exploring options for tickets in the morning.

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 December 23, 2025.
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
1,339 reviews

Boarding

7.6

Food

6.7

Comfort

7.4

Entertainment

6.9

Overall

7.6

Crew

8.1

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
Finnair
7.6
Good
1,339 reviews
Finnair
7.6
Good
1,339 reviews

Boarding

7.6

Food

6.7

Comfort

7.4

Entertainment

6.9

Overall

7.6

Crew

8.1

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
SWISS
7.5
Good
1,817 reviews
Finnair
7.6
Good
1,339 reviews

Boarding

7.6

Food

6.7

Comfort

7.4

Entertainment

6.9

Overall

7.6

Crew

8.1

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
Lufthansa
6.8
Okay
7,650 reviews
Finnair
7.6
Good
1,339 reviews

Boarding

7.6

Food

6.7

Comfort

7.4

Entertainment

6.9

Overall

7.6

Crew

8.1

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.
British Airways
6.7
Okay
7,607 reviews
Finnair
7.6
Good
1,339 reviews

Boarding

7.6

Food

6.7

Comfort

7.4

Entertainment

6.9

Overall

7.6

Crew

8.1

Reviews

1 / 20
6.0
Good

Rowland,Dec 2024

FRA - HEL

Finnair need to get a better system for boarding. Hundreds of passengers all attempting to get their boarding cards and passports checked at the gate and then get onto the aircraft is ridiculous, time consuming and frankly unfair to passengers.

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 Lufthansa, SWISS, and Air Canada fly from Chicago to Greek Islands in about 16h 10m. The time it takes to get you to your destination can typically vary by up to 22h 33m. The distance from Chicago to Greek Islands is about 5524 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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Alternative routes for Chicago to Greek Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Greek Islands

Discover the top 4 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$602Average$1,024FlexibilityNo cancel feeOn-time70%
FinnairCheapest$606Average$1,059FlexibilityNo cancel feeOn-time76%
LufthansaCheapest$842Average$1,188FlexibilityNo cancel feeOn-time76%
SWISSCheapest$893Average$1,218FlexibilityNo cancel feeOn-time79%

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