$289 Find Cheap Flights from Chicago to Greek Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Greek Islands departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Greek Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Greek Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Greek Islands.
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Best Greek Islands Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Thera
Thera1 stop$516
Heraklion
Heraklion2 stops$586
Mykonos
Mykonos1 stop$719
Chania
Chania1 stop$605
Corfu
Corfu2 stops$756
Rhodes
Rhodes2 stops$1,044
Parikia
Parikia3 stops$1,446
Kos
Kos1 stop$805
Naxos
Naxos2 stops$1,136
Zakynthos
Zakynthos1 stop$831
Argostoli
Argostoli3 stops$1,080
Paleochori
Paleochori3 stops$1,250
Chios
Chios3 stops$1,184
Sitia
Sitia2 stops$1,564
Thera
Thera1 stop$516
Heraklion
Heraklion2 stops$586
Mykonos
Mykonos1 stop$719
Chania
Chania1 stop$605
Corfu
Corfu2 stops$756
Rhodes
Rhodes2 stops$1,044
Parikia
Parikia3 stops$1,446
Kos
Kos1 stop$805
Naxos
Naxos2 stops$1,136
Zakynthos
Zakynthos1 stop$831
Argostoli
Argostoli3 stops$1,080
Paleochori
Paleochori3 stops$1,250
Chios
Chios3 stops$1,184
Sitia
Sitia2 stops$1,564

Cheap Flights from Chicago to Greek Islands

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Greek Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Greek Islands

Mon, Oct 27 - Tue, Nov 4
Lufthansa Logo
10:50 pm - 7:15 pmORD-JTR
13h 25m1 stop
Lufthansa Logo
8:05 pm - 6:25 pmJTR-ORD
30h 20m1 stop
$516Lufthansa
Find Deal
Mon, Oct 27 - Tue, Nov 4
Lufthansa Logo
10:50 pm - 7:15 pmORD-JTR
13h 25m1 stop
Lufthansa Logo
8:05 pm - 1:10 pmJTR-ORD
25h 05m2 stops
$527Lufthansa
Find Deal
Sun, Aug 10 - Mon, Aug 25
SWISS Logo
2:20 pm - 8:00 pmORD-JTR
21h 40m1 stop
SWISS Logo
8:45 pm - 12:10 pmJTR-ORD
23h 25m1 stop
$688SWISS
Find Deal
Sun, Aug 10 - Mon, Aug 18
SWISS Logo
7:05 pm - 7:05 pmORD-HER
16h 00m1 stop
SWISS Logo
7:55 pm - 3:55 pmHER-ORD
28h 00m1 stop
$698SWISS
Find Deal
Tue, Sep 2 - Wed, Sep 10
British Airways Logo
9:15 pm - 4:10 pmORD-HER
34h 55m1 stop
British Airways Logo
4:35 pm - 6:15 pmHER-ORD
33h 40m1 stop
$719British Airways
Find Deal
Sun, Sep 7 - Mon, Sep 15
British Airways Logo
9:15 pm - 8:50 pmORD-HER
15h 35m1 stop
British Airways Logo
4:20 pm - 1:50 pmHER-ORD
29h 30m1 stop
$727British Airways
Find Deal
Mon, Aug 18 - Mon, Sep 8
Finnair Logo
4:55 pm - 7:45 pmORD-CHQ
18h 50m2 stops
Finnair Logo
8:40 pm - 3:45 pmCHQ-ORD
27h 05m2 stops
$746Finnair
Find Deal
Mon, Aug 18 - Mon, Sep 8
Finnair Logo
9:30 pm - 7:45 pmORD-CHQ
14h 15m1 stop
Finnair Logo
8:40 pm - 3:45 pmCHQ-ORD
27h 05m2 stops
$802Finnair
Find Deal
Wed, Sep 17 - Wed, Sep 24
American Airlines Logo
1:59 pm - 7:40 pmORD-CHQ
21h 41m2 stops
American Airlines Logo
10:50 am - 7:33 amCHQ-ORD
28h 43m2 stops
$936American Airlines
Find Deal
Tue, Sep 16 - Wed, Sep 24
American Airlines Logo
9:24 am - 7:40 pmORD-CHQ
26h 16m2 stops
American Airlines Logo
10:50 am - 9:15 amCHQ-ORD
30h 25m2 stops
$943American Airlines
Find Deal
Useful Info

KAYAK's insights & trends for Chicago to Greek Islands flights

Get data-powered insights and trends into flights from Chicago to Greek Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Greek Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $951, prices are generally cheapest when you fly direct.


Good to know

Cheapest flight$289
Flight from Chicago to Santorini (Thira)

FAQs - booking Greek Islands flights

  • How does KAYAK find such low prices on flights from Chicago to Greek Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Greek Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Greek Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Greek Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Greek Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago to Greek Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Greek Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Greek Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Greek Islands?

    The cheapest time of day to fly to Greek Islands is generally in the afternoon, when round-trip flights cost $679 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Greek Islands is generally at night, which is peak travel time and where the average cost of a ticket is $916.

Reviews of the top 5 airlines serving from Chicago to Greek Islands

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Greek Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Greek Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.6
FinnairOverall score based on 1292 reviews
7.4Comfort
6.9Entertainment
7.6Boarding
8.1Crew
6.7Food
Airline reviews

Major problems checking in at Alaska counter. They could not find our booking code because it came from Finnair.

2.0 MediocreAnonymous, Jun 2025SAN - SEA
Read more Finnair reviews

Major problems checking in at Alaska counter. They could not find our booking code because it came from Finnair.

Do not use KAYAK or Finair for future travel. Unless you purchase the tickets directly from the airline, you were going to have a difficult time checking in. Kayak canceled my flights twice and ended up causing great difficulty in me getting back from Europe because they double sold my tickets between American Airlines and Finair. The event caused significant delays and led to me having to rebook my flights.

The staff were all particularly great. The plane was clean and fresh. The bassinet worked great. It was all very nice.

Boarding uncomfortable. Stewardess said I would have to check my carry on as there was no room in the overhead bins. Another passenger helped me find a spot.

Any flight that lands safely is a good flight. However our leg from Helsinki was delayed 1 hour with no explanation. The delay would not allow us to make our connection to Cincinnati. I was informed by American Airlines that our Cincinnati flight was rescheduled for the following day. I immediately made a non refundable hotel reservation in Dallas. Upon exiting the plane at Dallas I was given a hotel voucher. Nice, but I can't get a refund on the hotel I booked. A little communication would have been helpful. Food on Finnair is below quality of Korean Air.

The cabin crew really looked like they wanted to be somewhere else. They weren't really interested in providing an attentive service to full fare paying passengers at all. However the Captiain's in flight announcements were relaxed and very entertaining.

Crew were professional and responsive. Food was mediocre and breakfast could do with revampinmg

Food was very ordinary for premium economy, very small portions.

i dont know WHY they call it business class. the seats are NOT significantly wider than economy seats, they just do not let the middle seats be beepked to give the illusion of more space between passengers. the seats do NOT recline any more than economy seats either. the only real difference is the full meal served to business (vs none for economy). I would rather have a wider, lie flat ACTUAL business class seat with no food for a 3 hr flight. this was pretty disappointing to say the least.

There wore nice leather like sits, in my opinion seats lay out bit tight . Crew was great they did averything possible to make averywone comfortable as possible, food was, think worst I ever head on flight, head chicken and yellow rice. Ice cream was a nic treat.

The food was good. Most the staff was pleasant. The flight would be drastically improved with WiFi on a long international flight.

Each flight we took was late with little or no updates or information.

When I needed to get my bag off of the plane so that I could take a train because the connection was 4 hours later, they took 2 hours to take my bag off making me take the train and miss my flight simultaneously. The seat size on the plane is too small for an average aged woman let alone a middle-aged man. It's unacceptable and I will not fly Boeing again.

The cushion of the seats are old and very thin. The food can be more tasty or come with salt packages

The biggest let down was with booking experience through Kayak. I booked a flight with checked bags on Kayak. Right away I got a message from travel agency that the flight is not confirmed and to call them. I called them and they said the flight I have booked is no longer available with the price I have booked it for and I can book it with about $100 more. I already had other options I could book with cheaper price so I asked them to cancel my booking. Then they said I can have the ticket with the same price but a date change which was not working for me as I had to be there for a seminar. So again I said no then they said they will cover the charges and confirm my flight. When comes time for check-in I see I have no checked bag option which means the travel agency deceived me saying I can have my booking as I had booked it. And at that point I ended up paying $155 for my checked bag going back and forth. I am extremely angry and unhappy with this experience

PLEASE DONT TAKE FORCEFULLY(SIZE APPROPRIATE) CARRY ONS FROM PASSENGERS WHO FOR SOME REASON NEED TO KEEP IT

It was great. My seat was comfortable. The bathrooms were clean . The service was superb . I travel a lot and I have been in 64 counties. I wish I could fly first class, even though I could , but I prefer to budget my yearly travelling expense on actual visiting , not on flight. Anyway, my point is that your economy was far much better than other airlines as good as Air France. The flight attendants and all crew were polite and very helpful and respectful. Thank you for making my long trip tolerable.

I slept the whole flight so I can't tell you about the food and there was no entertainment offered. Crew was very nice, seats were comfortable in business, and boarding was easy.

I haven't flown Swiss in a long time. I was disappointed that after paying $14,907 for 3 business class seats, we still had to pay another $200 for a single business class seat. All the window seats used to be single seats. Now it's every other one and if you want a single seat it's extra. Also, The double seats do not have pods or any privacy. We landed in Chicago after a long 10 hour flight and our connecting flight was on United. Because we do not have status on Swiss, we were not allowed to use the United lounge, even with business class seats. My father is on crutches and we had a 4 hour layover. No lounge was also disappointing. All of my status is on British Airways so I will go back to flying BA. We flew Swiss because my father did not want to go through Heathrow. On a positive, the crew were super nice and accommodating for my father who had recently had hip replacement surgery. Food was okay. I"m not a good person to critique the food, I never like airplane food.

My luggage did not make the connection and 4 days later I still have not received it.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Cheapest airlines I have ever been on. I got downgraded and never got on united. I got rerouted through Vancouver onto jetwesf

Flight was 1.5 hours late to depart so changed flights to Swiss Air.

The United Airlines crew that operated this flight was subpar. They didn’t

Very small and uncomfortable seats, Hard to hear entertainment system sound. Horrible food. Staff doesn't care much about the passengers. 2nd time they didn't give me my vegetarian meal. They asked me regular food with meat. The airline and staff was from United airlines.

Checkin took along timen only.few angents available at.checkin desk. Customer support over phone no existence

At baggage claim, I was given the wrong printed ticket. The ticket belonged to another passenger for a different flight — to Zurich instead of Frankfurt (layover). I was even allowed to pass security, and when I asked the Lufthansa employee if I was on the correct flight, and why it was changed. The employee said everything was correct and I should board. When I got on the plane, there was someone in my seat, and the crew on the plane finally realized that I was on the wrong plane. When I got off the plane, nobody was willing to help, and the security refused to provide my original printed ticket. That was until I showed them that I took a photo of the ticket; once they realized I had photographic evidence, they were suddenly ready to help me. The Lufthansa employee began communicating with other airlines and found a flight that would take me to my destination via Polish Airlines. I was required to once again go through security, re-check my bag, and once again pay for my checked bag and weight overage fees. This experience was incredibly stressful and very frustrating, as you can imagine. A Lufthansa employee told me I would be eligible for a refund. Please tell me what steps I need to take in order to make that happen. Thank you!

The row of seats were so cramped it was difficult to get in and out of your seat. I even upgraded. A long flight and sad accommodations 😵‍💫 the shorter flight was very comfortable and the seating was spacious

Delayed over 2 hours. Bring your own snacks or prepare to pay. No entertainment and no plug plugs for charging.

I have flown with many airlines. My first time was several years ago. Now I remember why I avoided them for so long. Lufthanza is the only airline who has ever raised a size/weight issue with my modest standard size carry on. I had to repack three times to meet their carry-on weight criteria. (Apparently the rules of physics apply differently on Lufthansa flight than on other airlines.) In the meantime their staff was quite rude, repeating meaningless phrases like "Rules are Rules." And ignoring the additional fact that weight is also weight, whether it is in found in your carry on or in your suitcase. They eventually acknowledged that customer service and satisfaction is, for them, a low priority. Never choosing Lufthansa again.

They are professional. Nice crew. Still flying Boeing 747. Thank you for that. I love this airplane. Traditional.

More Indian vegetarian food options would have been better Availability of seat selection free of charge 72 hours before departure would be great

This was the second time on BA, food terrible, bathrooms gross,( granted, that was mostly due to the disgusting children urinating all over it)boarding was late and disorganized. No gate issued until last minute st Heathrow, bad system, caused undue stress. Seats were painful, that's what you get for traveling like a poor in economy, right BA? Should have been able to afford business or first class if you want to actually be able to walk upright without back pain after a trip.

This was the second time on BA, food terrible, bathrooms gross, boarding late and disorganized. No gate issued until last minute st Heathrow, bad system, caused undue stress.

The flight was delayed twice and because of that, we missed our connecting flight. British Airways then attempted to put us on the last flight to Milan from London which would have kept us in the airport for 12 hours. We had to speak to several levels of bureaucracy until BA management let us fly on a flight that only kept us in the airport for two hours. If there was an earlier flight, why weren’t we put on that flight from the start? Unacceptable behavior from what was once my favorite carrier.

The payment system was not working so was unable to connect wifi the entire flight

everything to do with KAYAK was terrible. Your customer facing departments are utterly useless, timewasting and unhelpful.

I ordered short ribs for main course. It tasted sweet, really sweet. Horrible.

Our luggage didn’t arrive with us, that puts a damper on the whole trip.

The screen didn’t work and I didn’t get the seat upgrade I paid $300 for. They were no help with that,

Paid $180 for seat selection, and selection essnt honored. Have to call for a refund.

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