$289 Find Cheap Flights from the Cayman Islands to Illinois - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from the Cayman Islands to Illinois departing on 11/28. 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, 0 bags

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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 5 days.

The cheapest ticket to Illinois from the Cayman Islands found in the last 5 days was to Chicago O'Hare Intl Airport, at $329 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 $329.

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

The average price for all round-trip flights from the Cayman Islands to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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 $707.

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 $457.

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Good to know

Cheapest flight$289
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 Saturday where round-trip tickets can be as cheap as $470. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $2,559 on average.

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.
7.1
American AirlinesOverall score based on 11782 reviews
6.4Food
7.2Comfort
7.5Boarding
7.9Crew
6.8Entertainment
Airline reviews

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

8.0 ExcellentJoseph, Jul 2026
STL - ORD
Read more American Airlines reviews

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

I love the e fact that the staff communicated swiftly when my flight was delayed and gate number changed

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

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 $329