$344 Find Cheap Flights from Chicago to Greek Islands - Compare and Save

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Cheap Flights from Chicago to Greek Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Thera
Thera1 stop$829
Heraklion
Heraklion1 stop$748
Mykonos
Mykonos2 stops$860
Chania
Chania2 stops$833
Corfu
Corfu2 stops$789
Rhodes
Rhodes2 stops$995
Parikia
Parikia2 stops$950
Naxos
Naxos2 stops$1,001
Kos
Kos2 stops$1,058
Argostoli
Argostoli3 stops$1,099
Zakynthos
Zakynthos2 stops$901
Paleochori
Paleochori2 stops$1,007
Chios
Chios2 stops$1,903
Thera
Thera1 stop$829
Heraklion
Heraklion1 stop$748
Mykonos
Mykonos2 stops$860
Chania
Chania2 stops$833
Corfu
Corfu2 stops$789
Rhodes
Rhodes2 stops$995
Parikia
Parikia2 stops$950
Naxos
Naxos2 stops$1,001
Kos
Kos2 stops$1,058
Argostoli
Argostoli3 stops$1,099
Zakynthos
Zakynthos2 stops$901
Paleochori
Paleochori2 stops$1,007
Chios
Chios2 stops$1,903
Booking Insights

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?

No, with an average price for the route of $499, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight

$344
Flight from Chicago to Rhodes

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.

Reviews of the top 3 airlines serving from Chicago to Greek Islands

 
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.
7.5
SWISSOverall score based on 2060 reviews
8.2Crew
7.1Food
7.4Comfort
7.7Boarding
6.8Entertainment
Airline reviews

Wonderful, i asked at front gate to change my seat up closer and they gave me a row with no one in it. Very kind of them as the flight was on the light side.

10.0 ExcellentSusan, Aug 2026
Read more SWISS reviews

Wonderful, i asked at front gate to change my seat up closer and they gave me a row with no one in it. Very kind of them as the flight was on the light side.

Great crew, great food, horrible aircraft seat spacing for a 9 hr flight.

Didn't make the connection as my primary flight was 3 hrs late, I had to basically beg to be put on a different airline to continue my trip otherwise I would have been sitting on the airport for 8 hrs

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.

The seats had no space at all beyond the knees. The seat in-front literally reclined on your face, very uncomfortable plane. Was nothing like the normal SWISS experience. The food was okay but could be better.

They rebooked our flight and then canceled our trip halfway through the journey without any explanation. Needed to pay by ourselves for alternative flight options without any help from Swiss.

Easy boarding Seats were very uncomfortable no room arm rests didn't even go up all the way

Wonderful experience! The crew was outstanding and amazing from check in to gate to flight crew! Amazing. Thank you!

Carry on luggage size for economy passengers significantly smaller than other airlines, so nearly all ecomy passengers had their bags taken and checked.

Missed connecting train since flight was late into Zurich and I had to stay at airport hotel because of it as well as I had to repurchase train ticket

Flight was on time and got us to destination quicker than scheduled.

I have very bad experience with United because Vince two weeks that I did not receive my luggage yet

It was okay. Mothers with rowdy children should be invited to sit in front of them.

Good food, overall very comfy. The flight was full so obviously not optimal, but it is what it is.

Flight was delayed by several hours and then cancelled due to weather. But Staff was very helpful getting me on a different flight. United should offer food coupons and tooth brush and paste for stranded passengers

I had a good comfortable seat. There was nearly an hour delay. There was an accident with the champagne, but I was well compensated. These things happen sometimes.

We missed our flight. There was not enough time built into the layover to get through immigration, customs, bagclaim, bag rechecking, and the long trip to another terminal and gate. Kayak really screwed up. We took the bus up to Wisconsin and then were picked up in Brookfield by private car. It was lucky we didnt miss the last bus out.

I tried both on line and by calling the Customer Service line to arrange for a special meal as i have food intolerances. I was under the impression from your service representative that I was successful. I was not. I cannot eat spicy foods and get very ill if i eat bell peppers. I could not eat either menu choice and no special meal was actually ordered. ( your representative tried to order it for a flight that did not have meal service!!! - found this out later). Your wonderful cabin crew managed to put together a fruit, salad, roll and cheese tray for me so I had something to eat. WHY WOULD YOU SERVE SPICY FOOD, WITH NO MILDER OPTION,ON AN INTERNATIONAL FLIGHT???

I liked Quiet people around me. Crew could have helped people with overhead luggage so they aren't moving other peoples bags around and causing problems for people that had there bags there first

The plane was delayed by two hours in Chicago which led to us missing the next flight. Lufthansa rebooked the flight and booked us a hotel for the night in Frankfurt. The level of customer service and getting us taken care of was superb. The flight crew and the service on the ground was superb.

Comfortable seats, good service overall. The food could’ve been a little bit better. The boarding process was slightly chaotic and in fairness, not all of that is related to the performance of British Airways.

They gave away my business class seat. No explanation and no apology. Told me I had to take the downgrade if I wanted to get to India. Then no WiFi for 10 hours. Just ridiculous. We should not work with this company at Deloitte. They don’t know how to run a business.

It's hard to tell where to plug in electronics, and the port on my seat didn't work. Their entertainment system was down. Vegetarian food options were tasty. Friendly, helpful flight attendants.

Lady next to me was coughing profusely the entire flight, other lady moved seats because of it, 8 hours of that during an overnight flight is a bit much.

The seats are extra cramped if you are taller than 5’8! Spring for the extra legroom seats for sure if you have a long flight!

Very disappointed with British Airways. It has been over 24 hours and I still have not received my checked baggage or any proper update. Customer support has been unresponsive, making the situation even more frustrating. Poor baggage handling and lack of communication seriously impacted my travel experience.

Cancelled flight and re booked seats were a downgrade. British Airways said the upgrade was t available but when I checked it was but then they wouldn’t make it right

Overall ok. Best part has always been the sundae dessert.

Very good staff members with sincere passion and responsibility in their job.

Boarding was efficient and quick, crew was very attentive, seats were comfortable.

Everything you need to know for your flight to Greek Islands

Information on your arrival and departure airports