$199 Find Cheap Flights from the Cayman Islands to Illinois

1 adult
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Illinois, as well as popular online travel agencies
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Booking Insights

KAYAK's insights & trends for flights to Illinois

Get data-powered insights and trends for flights to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Illinois?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to Illinois from the Cayman Islands found in the last 72 hours was to Chicago O'Hare Intl Airport, at $276 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 72 hours was $276.

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 $318.

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Good to know

Low seasonFebruary
Cheapest flight$199
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from George Town to Chicago

FAQs for booking flights from the Cayman Islands to Illinois

  • How does KAYAK find such low prices on flights from the Cayman Islands 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 the Cayman Islands to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from the Cayman Islands 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 the Cayman Islands 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 the Cayman Islands 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 the Cayman Islands 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 the Cayman Islands to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Sunday where round-trip tickets can be as cheap as $373. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $1,469 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 $497 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 $707.

Reviews of the top airline flying from the Cayman Islands to Illinois

 
See real verified KAYAK customer reviews for airlines flying to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the Cayman Islands to Illinois. 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 the Cayman Islands 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.
7.2
American AirlinesOverall score based on 11211 reviews
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
8.0Crew
Airline reviews

Flight from CHI to PVD was delayed by over 20 hours.

4.0 OkayJonathan, Feb 2026
MEX - ORD
Read more American Airlines reviews

Flight from CHI to PVD was delayed by over 20 hours.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Illinois
Business Class flights to Illinoisfrom $6,093
Premium Economy Class flights to Illinoisfrom $1,722
Economy Class flights to Illinoisfrom $276