Statistics on Chicago-Cayman Islands (Georgetown (Grand Cayman)) flights: what is the right price and when to buy your plane ticket?
Best time to go: what is the RIGHT price for a round-trip flight to the Cayman Islands (Georgetown (Grand Cayman)) (from: Chicago)
The average price to go to the Cayman Islands (Georgetown (Grand Cayman)) from Chicago airport is $ 621 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 505 (in september) and $ 888 (in march), which is a saving of $ 117 or a surplus of $ 267 (compared to the average price) depending on the period you leave.
The analysis of all prices reveals that the most frequent price is between $486 to $540 and it is generally more economical to leave on a tuesday and return on a tuesday on a flight with 1 or more layovers.
Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to the Cayman Islands (Georgetown (Grand Cayman)) before booking your flight.
If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your Chicago-Cayman Islands (Georgetown (Grand Cayman)) plane ticket.
How are these data calculated?
We have studied a sample of 14937 airfare prices from previous years for flights to the Cayman Islands (Georgetown (Grand Cayman)) from Chicago and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.
Average price depending on the departure month
Data analysis:
By leaving in september, the price of the plane ticket will statistically be the cheapest ($ 505, saving $ 117 compared to the average price over the year which is $ 621). Conversely, march will be the most expensive ($ 888).
Flight Chicago-Cayman Islands (Georgetown (Grand Cayman)): when is the best time to go for the best price?
| Month | Good price* | Average price | Our opinion |
|---|---|---|---|
| January | $ 472 | $ 560 | good price |
| February | $ 471 | $ 584 | good price |
| March | $ 534 | $ 888 the most expensive | very high price |
| April | $ 508 | $ 682 | fair price |
| May | $ 488 | $ 558 | good price |
| June | $ 513 | $ 590 | good price |
| July | $ 555 | $ 607 | good price |
| August | $ 486 | $ 543 | good price |
| September | $ 452 | $ 505 the cheapest | very good price |
| October | $ 461 | $ 549 | good price |
| November | $ 527 | $ 716 | fair price |
| December | $ 511 | $ 660 | fair price |
*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!
Price breakdown to travel from Chicago to the Cayman Islands (Georgetown (Grand Cayman))
Data analysis:
The prices for flights from Chicago to Cayman Islands (Georgetown (Grand Cayman)) range from $324 to $972. 3% of tickets were purchased at the minimum price (from $324 to $378), 1% at the maximum price (from $918 to $972). The majority of plane tickets were purchased in the range of $486 to $540 (16% of tickets).
Cheapest airlines for the Chicago->Cayman Islands flight
There are 8 companies that serve Chicago from Cayman Islands (Georgetown (Grand Cayman)) airport: United, Spirit Airlines, American Airlines, Frontier Airlines, Delta, jetBlue, Air Canada and Iberia.
Data analysis:
Of the 14937 flights analyzed in previous years, United was the airline that offered the best fare most often in the flight ticket search results (30% of the time) on the Chicago->Cayman Islands route.
Direct flight or flight with layover?
Data analysis:
To get the best price for the Chicago-Cayman Islands (Georgetown (Grand Cayman)) flight, you should take a flight with one or more layovers (you will save an average of $ 487 compared to a direct flight).
Which day of the week to leave?
Data analysis:
Statistically, Chicago-Cayman Islands (Georgetown (Grand Cayman)) flights departing on a tuesday are cheaper than on other days of the week. By choosing a tuesday as your departure date, you can save an average of $124. On the other hand, departing on a saturday may cost you an additional $132.
Which day of the week to come back?
Data analysis:
Statistically, return flights from Cayman Islands (Georgetown (Grand Cayman)) to Chicago departing on a tuesday are cheaper than on other days of the week. By choosing a tuesday for your return date, you will save an average of $132. Conversely, departing from Cayman Islands (Georgetown (Grand Cayman)) on a saturday may cost you an additional $128.
Top prices Chicago-Cayman Islands (Georgetown (Grand Cayman))
| Round trip | Dates | Price | |
|---|---|---|---|
| Chicago → Georgetown (Grand Cayman) | 05-04 to 11-04-2025 | $ 548 | layover flight with Air Canada |
| Chicago → Georgetown (Grand Cayman) | 06-04 to 12-04-2025 | $ 575 | layover flight with Air Canada |
| Chicago → Georgetown (Grand Cayman) | 07-04 to 14-04-2025 | $ 500 | layover flight with Air Canada |
| Chicago → Georgetown (Grand Cayman) | 06-05 to 11-05-2025 | $ 521 | layover flight with Spirit Airlines |
| Chicago → Georgetown (Grand Cayman) | 10-05 to 17-05-2025 | $ 538 | layover flight with Spirit Airlines |
| Chicago → Georgetown (Grand Cayman) | 12-05 to 19-05-2025 | $ 520 | layover flight with Frontier Airlines |
| Chicago → Georgetown (Grand Cayman) | 14-05 to 19-05-2025 | $ 507 | layover flight with Allegiant Air |
| Chicago → Georgetown (Grand Cayman) | 15-05 to 22-05-2025 | $ 577 | layover flight with Frontier Airlines |
| Chicago → Georgetown (Grand Cayman) | 25-09 to 29-09-2025 | $ 564 | layover flight with Spirit Airlines |
| Chicago → Georgetown (Grand Cayman) | 04-10 to 11-10-2025 | $ 567 | layover flight with Spirit Airlines |
When to book your flight Chicago - Cayman Islands (Georgetown (Grand Cayman)) to get the cheapest price?
Statistically, you will make the biggest savings by buying your plane ticket between 1 to 2 months in advance. However, you may end up paying a high price if you book between 10 to 11 months in advance.
Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a Chicago-Cayman Islands flight, it is recommended to book your ticket on a sunday.
How far in advance should I buy my flight?
Data analysis:
To get the cheapest flight ticket from Chicago to the Cayman Islands (Georgetown (Grand Cayman)), it is recommended to buy it 1 to 2 months before departure (it is then on average 566 $, which is a saving of 55 $ compared to the overall average price). On the other hand, if you buy your ticket 10 to 11 months in advance, you will pay the full price (442 $ more than the average price).
Depending on the departure month
The best time to buy your Chicago to the Cayman Islands (Georgetown (Grand Cayman)) flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.
| Departure on... | How far in advance should I book? |
|---|---|
| January | Best time: 6 to 7 months before departure (average price: 492 $) Other interesting period(s): 1 to 2 months ($ 519), 2 to 3 months ($ 549), 4 to 5 months ($ 538), 5 to 6 months ($ 525) |
| February | Best time: 2 to 3 months before departure (average price: 521 $) Other interesting period(s): 1 to 2 months ($ 525) |
| March | Best time: 0 to 1 month before departure (average price: 700 $) Other interesting period(s): 1 to 2 months ($ 720) |
| April | Best time: 2 to 3 months before departure (average price: 556 $) Other interesting period(s): 0 to 1 month ($ 656), 1 to 2 months ($ 590), 3 to 4 months ($ 676) |
| May | Best time: 1 to 2 months before departure (average price: 519 $) Other interesting period(s): 3 to 4 months ($ 526) |
| June | Best time: 1 to 2 months before departure (average price: 540 $) Other interesting period(s): 2 to 3 months ($ 567), 4 to 5 months ($ 564) |
| July | Best time: 1 to 2 months before departure (average price: 557 $) Other interesting period(s): 2 to 3 months ($ 593) |
| August | Best time: 2 to 3 months before departure (average price: 487 $) Other interesting period(s): 1 to 2 months ($ 488) |
| September | Best time: 2 to 3 months before departure (average price: 461 $) Other interesting period(s): 1 to 2 months ($ 490), 3 to 4 months ($ 472) |
| October | Best time: 3 to 4 months before departure (average price: 455 $) Other interesting period(s): 1 to 2 months ($ 496), 2 to 3 months ($ 503) |
| November | Best time: 1 to 2 months before departure (average price: 574 $) Other interesting period(s): 2 to 3 months ($ 600), 6 to 7 months ($ 658) |
| December | Best time: 1 to 2 months before departure (average price: 547 $) Other interesting period(s): 0 to 1 month ($ 633), 2 to 3 months ($ 614), 5 to 6 months ($ 623) |
What day of the week should I book my flight ticket?
Data analysis:
Statistically, sunday is the day when plane tickets for Chicago->Cayman Islands are the cheapest. So, by buying your plane ticket on a sunday, you will save $14. Conversely, by buying it on a monday, you may end up paying $20 more.
Chicago to the Cayman Islands (Georgetown (Grand Cayman)): flight price when booking today
Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.
| Month | Current price | Our opinion | |
|---|---|---|---|
| April 2025 | $ 764 $500 to $1435 | high price | Find a flight |
| May 2025 | $ 566 $496 to $728 | high price | Find a flight |
| June 2025 | $ 615 $615 to $615 | high price | Find a flight |
| July 2025 | $ 622 $585 to $653 | high price | Find a flight |
| September 2025 | $ 564 $564 to $564 | high price | Find a flight |
| October 2025 | $ 573 $567 to $578 | high price | Find a flight |
| December 2025 | $ 755 $619 to $823 | high price | Find a flight |
| January 2026 | $ 635 $610 to $659 | high price | Find a flight |
| February 2026 | $ 634 $634 to $634 | high price | Find a flight |
Data analysis:
Compared to the average price, no month is currently cheaper. We therefore advise you to wait for prices to drop before booking your flight to the Cayman Islands (Georgetown (Grand Cayman)).