$232 Find Cheap Flights from Grand Cayman to Illinois

1 adult
1 adult, Economy, 0 bags

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Useful Info

Good to know

Low seasonNovember
Cheapest flight$232
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from George Town to Chicago

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 92% 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 $448.

  • 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 $381. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $2,559 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 $597 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.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Grand Cayman found in the last 72 hours was to Chicago O'Hare Intl Airport, at $381 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 $381.

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

    The cheapest month for flights from Grand Cayman to Illinois is January, when tickets cost $389 (return) on average. On the other hand, the most expensive months are May and March, when the average cost of round-trip tickets is $711 and $646 respectively.

  • How many cities have direct flights to Illinois?

    From Grand Cayman, there are direct flights to Illinois from 1 city. This city is George Town and there are 7 direct flights each week.

  • How many direct flights to Illinois are there each day?

    There are around 1 direct flights from within Grand Cayman to Illinois every day. All flights depart in the afternoon.

  • How many direct flights to Illinois are there each week?

    Each week there are around 7 direct flights from within Grand Cayman to Illinois. The most common day for departures is Monday, with 14% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Grand Cayman to Illinois takes 5h 56m, 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 23m.

  • How many long-haul flights are there to Illinois each week?

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Illinois. Instead, there are 7 medium-haul flights (3-6 hour flight duration), with the most arriving from George Town.

  • 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.
7.1
American AirlinesOverall score based on 11604 reviews
6.9Entertainment
6.4Food
7.5Boarding
7.2Comfort
7.9Crew
Airline reviews

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

10.0 ExcellentAnonymous, Apr 2026
GSP - ORD
Read more American Airlines reviews

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Boarding was quick and efficient. We arrived at our destination early.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Everything you need to know for your flight to Illinois

Cabin class types available on flights to Grand Cayman

Cabin classes available on flights to Grand Cayman. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Illinoisfrom $320
Business Class flights to Illinoisfrom $358
Premium Economy Class flights to Illinoisfrom $133
Economy Class flights to Illinoisfrom $52