$156 Find Cheap Flights from Illinois to the Cayman Islands

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Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$156
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Chicago O'Hare 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 $288.

  • 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 Monday where round-trip tickets can be as cheap as $668. 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 43% 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 $726.

  • 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 $429 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 $429.

  • 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 $565 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $866 and $833 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 14 weeks before departure.

  • How long is the flight to the Cayman Islands?

    An average nonstop flight from Illinois to the Cayman Islands takes 10h 10m, 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 3h 56m.

  • 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%).

Book cheap flights from Illinois to the Cayman Islands

Recent round-trip flight deals

10/24Fri
2 stopsAir Canada
41h 14mORD-GCM
10/31Fri
1 stopAir Canada
28h 58mGCM-ORD
$452
8/1Fri
1 stopUnited Airlines
6h 15mSTL-GCM
8/9Sat
1 stopUnited Airlines
16h 43mGCM-STL
$454
8/15Fri
2 stopsAmerican Airlines
18h 16mSTL-GCM
8/22Fri
1 stopAmerican Airlines
11h 49mGCM-STL
$458
7/23Wed
1 stop
27h 31mORD-GCM
7/28Mon
1 stop
23h 26mGCM-ORD
$460
9/25Thu
2 stopsAmerican Airlines
19h 23mSTL-GCM
9/28Sun
1 stopAmerican Airlines
11h 25mGCM-STL
$463
7/29Tue
1 stop
8h 01mORD-GCM
8/5Tue
1 stop
28h 41mGCM-ORD
$464
11/3Mon
1 stopSouthwest
5h 30mORD-GCM
11/14Fri
1 stopSouthwest
9h 20mGCM-ORD
$493
12/24Wed
1 stopDelta
5h 50mORD-GCM
12/31Wed
1 stopDelta
9h 13mGCM-ORD
$520
10/5Sun
2 stopsDelta
26h 32mORD-GCM
10/9Thu
2 stopsDelta
20h 23mGCM-ORD
$524
7/17Thu
1 stopSouthwest
6h 50mMDW-GCM
7/22Tue
1 stopSouthwest
6h 40mGCM-MDW
$573

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Recent one-way flight deals

7/23Wed
1 stop
8h 01mORD-GCM
$156
10/1Wed
2 stopsAir Canada
27h 15mORD-GCM
$168
10/31Fri
1 stopJetBlue
14h 50mORD-GCM
$172
10/12Sun
1 stopAir Canada
23h 55mORD-GCM
$179
10/25Sat
1 stopAir Canada
17h 00mORD-GCM
$182
10/29Wed
2 stopsAir Canada
22h 30mORD-GCM
$186
8/20Wed
1 stop
25h 13mORD-GCM
$187
11/1Sat
2 stopsSouthwest
19h 10mORD-GCM
$247
8/2Sat
1 stopSouthwest
6h 10mORD-GCM
$281
8/20Wed
2 stopsDelta
22h 29mMDW-GCM
$299

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Last minute flights from Illinois to the Cayman Islands

Last minute flight, train and bus deals

7/6Sun
multi-stopAmerican Airlines
16h 24mORD-GCM
7/15Tue
multi-stopAmerican Airlines
6h 51mGCM-ORD
$880
7/6Sun
multi-stopAmerican Airlines
6h 07mORD-GCM
7/15Tue
multi-stopAmerican Airlines
11h 04mGCM-ORD
$884
7/4Fri
multi-stop
9h 48mORD-GCM
7/7Mon
multi-stop
8h 39mGCM-ORD
$929
7/6Sun
multi-stopAmerican Airlines
16h 57mORD-GCM
7/15Tue
multi-stopAmerican Airlines
6h 51mGCM-ORD
$930
7/6Sun
multi-stopAmerican Airlines
7h 55mORD-GCM
7/15Tue
multi-stopAmerican Airlines
9h 06mGCM-ORD
$934
7/4Fri
multi-stop
15h 29mORD-GCM
7/7Mon
multi-stop
13h 05mGCM-ORD
$1,117
7/4Fri
multi-stopSouthwest
5h 20mMDW-GCM
7/7Mon
multi-stopSouthwest
9h 20mGCM-MDW
$1,171
7/4Fri
multi-stopSouthwest
5h 20mMDW-GCM
7/7Mon
multi-stopSouthwest
11h 25mGCM-MDW
$1,175
7/6Sun
multi-stopWestJet
41h 45mORD-GCM
7/15Tue
multi-stopWestJet
23h 05mGCM-ORD
$3,339
7/6Sun
multi-stopWestJet
43h 40mORD-GCM
7/15Tue
multi-stopWestJet
30h 30mGCM-ORD
$3,359

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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.
First Class flights to the Cayman Islandsfrom $657
Business Class flights to the Cayman Islandsfrom $1,598
Prem Econ Class flights to the Cayman Islandsfrom $2,001
Economy Class flights to the Cayman Islandsfrom $429

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