$222 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$222
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 15% 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 $357.

  • 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.

  • 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 $418 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 $418.

  • 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 25 direct flights each week.

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

    There are around 4 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 25 direct flights from within Grand Cayman to Illinois. The most common day for departures is Monday, with 16% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Grand Cayman to Illinois takes 7h 41m, 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 25 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 11381 reviews
6.9Entertainment
7.2Comfort
7.5Boarding
8.0Crew
6.4Food
Airline reviews

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

6.0 GoodIrene, Mar 2026
SFO - ORD
Read more American Airlines reviews

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

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 $155
Business Class flights to Illinoisfrom $271
Premium Economy Class flights to Illinoisfrom $156
Economy Class flights to Illinoisfrom $48