$206 Find Cheap Flights from Illinois to the Cayman Islands

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Good to know

Low season

September

High season

March

Cheapest flight

$206
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago Midway Airport to George Town

FAQs for booking flights from Illinois to the Cayman Islands

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

    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 Illinois to the Cayman Islands.

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

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

    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 Illinois to the Cayman Islands 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 Illinois to the Cayman Islands?

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

  • Which is the cheapest airport to fly into in the Cayman Islands?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in the Cayman Islands is George Town Owen Roberts Intl Airport (GCM), with an average flight price of $453.

  • What is the cheapest day to fly to the Cayman Islands?

    Based on KAYAK data, the cheapest day to fly to the Cayman Islands is Sunday where round-trip tickets can be as cheap as $688. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $1,039 on average.

  • What is the cheapest time of day to fly to the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $507 on average. Morning departures are around 41% more expensive than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $713.

  • What is the cheapest flight to the Cayman Islands?

    The cheapest ticket to the Cayman Islands from Illinois found in the last 72 hours was to George Town, at $645 round-trip. The most popular route is Chicago O'Hare Intl Airport (ORD) to George Town (GCM) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $645.

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

    The cheapest month for flights from Illinois to the Cayman Islands is September, when tickets cost $505 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $881 and $845 respectively.

  • How far in advance should I book a flight from Illinois to the Cayman Islands?

    To get a below average price on the flight from Illinois to the Cayman Islands, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

  • How long is the flight to the Cayman Islands?

    An average nonstop flight from Illinois to the Cayman Islands takes 15h 07m, covering a distance of 1558 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to George Town (GCM) with an average flight time of 4h 04m.

  • What are the most popular destinations in the Cayman Islands?

    Based on KAYAK flight searches, the most popular destination is George Town (99% of total searches to the Cayman Islands). The next most popular destination is Cayman Brac (1%).

See more FAQs

Book cheap flights from Illinois to the Cayman Islands

Recent round-trip flight deals

5/6Tue
1 stop
21h 10mORD-GCM
5/10Sat
1 stop
8h 51mGCM-ORD
$464
4/19Sat
1 stopAmerican Airlines
6h 51mSTL-GCM
5/3Sat
1 stopAmerican Airlines
8h 36mGCM-STL
$484
4/19Sat
2 stopsAmerican Airlines
16h 05mSTL-GCM
5/3Sat
1 stopAmerican Airlines
7h 28mGCM-STL
$488
5/3Sat
2 stops
29h 45mORD-GCM
5/10Sat
1 stop
8h 51mGCM-ORD
$492
4/30Wed
2 stops
29h 48mORD-GCM
5/10Sat
1 stop
8h 51mGCM-ORD
$510
6/1Sun
1 stopAir Canada
15h 30mORD-GCM
6/5Thu
1 stopAir Canada
20h 19mGCM-ORD
$518
6/13Fri
1 stopSouthwest
6h 50mMDW-GCM
6/17Tue
1 stopSouthwest
6h 40mGCM-MDW
$616
6/13Fri
1 stopSouthwest
12h 50mMDW-GCM
6/17Tue
2 stopsSouthwest
10h 40mGCM-MDW
$620
5/15Thu
1 stopDelta
5h 50mORD-GCM
5/22Thu
1 stopDelta
8h 45mGCM-ORD
$635
8/30Sat
1 stopDelta
5h 31mMDW-GCM
9/4Thu
1 stopDelta
8h 57mGCM-MDW
$635

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Recent one-way flight deals

5/1Thu
1 stop
23h 45mMDW-GCM
$206
5/19Mon
1 stop
11h 25mORD-GCM
$211
8/3Sun
1 stopSouthwest
5h 50mORD-GCM
$217
5/5Mon
1 stopSouthwest
6h 00mMDW-GCM
$217
8/10Sun
2 stopsAir Canada
20h 20mORD-GCM
$231
8/9Sat
2 stopsAir Canada
41h 40mORD-GCM
$236
8/11Mon
1 stopDelta
5h 31mORD-GCM
$293
8/10Sun
1 stopDelta
5h 31mMDW-GCM
$293
5/17Sat
2 stopsAmerican Airlines
14h 53mORD-GCM
$294
8/2Sat
2 stopsAmerican Airlines
9h 00mORD-GCM
$318

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Last minute flights from Illinois to the Cayman Islands

Last minute flight, train and bus deals

4/6Sun
multi-stop
12h 05mMDW-GCM
4/8Tue
multi-stop
26h 18mGCM-MDW
$678
4/6Sun
multi-stopSouthwest
6h 45mMDW-GCM
4/8Tue
multi-stopSouthwest
7h 30mGCM-MDW
$726
4/6Sun
multi-stopSouthwest
14h 30mMDW-GCM
4/8Tue
multi-stopSouthwest
10h 25mGCM-MDW
$730

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Everything you need to know for your flight to the Cayman Islands

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.

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