Find cheap flights from Grand Cayman to Illinois - Compare and Save

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FAQs for booking flights from Grand Cayman to Illinois

  • How does KAYAK find such low prices on flights from Grand Cayman to Illinois?

    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 Grand Cayman to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Grand Cayman to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Grand Cayman to Illinois 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 Grand Cayman to Illinois?

    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 Grand Cayman to Illinois 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 Grand Cayman to Illinois?

    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 Grand Cayman to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 93% of all flights arriving there.

  • Which is the cheapest airport to fly into in Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago O'Hare Intl Airport (ORD), with an average flight price of $418.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Saturday where round-trip tickets can be as cheap as $537. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $1,941 on average.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost $571 on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $666.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Grand Cayman found in the last 5 days was to Chicago O'Hare Intl Airport, at $376 round-trip. The most popular route is George Town (GCM) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 5 days was $376.

  • What is the cheapest month to fly from Grand Cayman to Illinois?

    The cheapest month for flights from Grand Cayman to Illinois is July, when tickets cost $247 (return) on average. On the other hand, the most expensive months are January and September, when the average cost of round-trip tickets is $761 and $568 respectively.

  • How long is the flight to Illinois?

    An average nonstop flight from Grand Cayman to Illinois takes 5h 21m, covering a distance of 1605 miles. The shortest route is George Town (GCM) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 4h 18m.

  • What is the most popular destination in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (100% of total searches to Illinois).

Reviews of the top airline flying from Grand Cayman to Illinois

 
Need help choosing which airline to fly with from Grand Cayman to Illinois? 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.
7.0
American AirlinesOverall score based on 12190 reviews
6.4Food
7.9Crew
6.8Entertainment
7.4Boarding
7.1Comfort
Airline reviews

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

2.0 MediocreScott, Oct 2026
Read more American Airlines reviews

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

The delay update was very late. I had a stressful short connection and RAN through Chicago to get to the next flight, only to find the plane wasn't at the gate yet an nobody was boarding. I would not have had to run if the delay was updated earlier.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Same the delay was not ideal and the credits to move flights was not sufficient

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

The crew were diligent about ensuring that our pet dog remained in his carrier for the entire flight, as is their mandate. I wish that mandate was changed so that our poor, scared pets can be comforted during a flight, whereas service animals get to stay out and about for the whole flight. Thank you.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

12 hour wait in pdx to my initial flight to Dallas to hunstville

The flight from Chicago to Orlando was delayed inordinately. My whole journey from Lansing to MCO took 9.5 hours is just annoying and frustrating. We can understand the delays may be beyond their control, but overall the journey was so much waiting until reached to MCO. This is NOT the first time for me - but at least 80% of the time in this route. I barely remember reaching places on time.

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