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$208 Cheap Flights from Chicago to Cayman Islands

Compare flights from Chicago to Cayman Islands

Find the cheapest month or even day of the year to fly

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Where in Cayman Islands would you like to go?

There are lots of destinations to choose from when you're planning your trip from Chicago to Cayman Islands.
George Town
1+ stopsFrom $565
Cayman Brac
1+ stopsFrom $907
Little Cayman
1+ stopsFrom $1,701
See more destinations

Flying from Chicago to Cayman Islands

The things to know before you go.
Cheapest flight ticket found$565
Cheapest month to flyJanuary
Average flight time4 hrs, 2 mins
Places to go3
Most popular airlineAmerican Airlines
Average flights per week8

Cheapest time to fly from Chicago to Cayman Islands

Looking for the cheapest ticket prices to Cayman Islands from Chicago? We can help you pick the cheapest month to fly.
Jul
Find prices
Aug
from $767
Sep
from $600
Oct
from $684
Nov
from $622
Dec
from $724
Jan
from $565
Feb
from $666
Mar
from $727
Apr
from $726
May
from $2,619
Jun
from $815

Chicago to Cayman Islands flight deals

Looking for a cheap last-minute deal or the best return flight from Chicago to Cayman Islands? If you want to travel next month, return fares start from $767. Find the lowest prices on one-way and return flight tickets right here.
George Town.$565 per passenger.Departing Wed, 6 Jan, returning Wed, 20 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 6 Jan, arriving in Owen Roberts International.Inbound indirect flight with Southwest Airlines, departs from Owen Roberts International on Wed, 20 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $565, select.
Cayman Brac.$907 per passenger.Departing Sat, 12 Sep, returning Sat, 19 Sep.Return flight with Frontier Airlines and Cayman Airways.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 12 Sep, arriving in Charles Kirkconnell International.Inbound indirect flight with Cayman Airways, departs from Charles Kirkconnell International on Sat, 19 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $907, select.
Little Cayman.$1,701 per passenger.Departing Sat, 12 Sep, returning Sat, 19 Sep.Return flight with jetBlue and Cayman Airways.Outbound indirect flight with jetBlue, departs from Chicago O'Hare International on Sat, 12 Sep, arriving in Edward Bodden.Inbound indirect flight with Cayman Airways, departs from Edward Bodden on Sat, 19 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $1,701, select.
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Flights from Chicago to Cayman Islands FAQs

The cheapest month to fly from Chicago to Cayman Islands is January. See if any of these flights in January suit you.
We've taken a look at the year ahead using our flights calendar. The cheapest flight route from Chicago to Cayman Islands is Chicago to Owen Roberts International. You can buy a ticket to fly this route from $565.

Take a look at Chicago to Owen Roberts International flights.
The average flight time from Chicago to Cayman Islands is 4 hours and 2 minutes.
Looking at the year ahead, the cheapest airline flying to Cayman Islands from Chicago is Southwest Airlines.

Explore Southwest Airlines flight ticket options today. 

If this airline doesn't suit you, the second cheapest airline is United.

How to find cheap flights from Chicago to Cayman Islands

  • $565 is currently the cheapest price for a return flight from Chicago to Cayman Islands.

  • That fare gets you from Chicago to Owen Roberts International in George Town.

  • $208 is the lowest price for a one-way journey.

  • Open to where you land? Enter 'Cayman Islands' in the 'To' field to compare fares to different cities.

  • Choose 'Add nearby airports' to broaden your search and compare prices across all airports close to both your departure and destination cities.

  • Early booking can pay off. Fares tend to rise as your departure date gets closer, not drop.

  • Know the moment fares change. Download the Skyscanner app, create a Price Alert, and we'll keep you updated when prices rise or drop.

Best time to fly from Chicago to Cayman Islands

  • January is usually the cheapest month to catch a flight from Chicago to Cayman Islands.

  • Flying midweek can often work in your favor. Fares are generally lower on Tuesdays and Wednesdays compared to the rest of the week.

  • The height of the travel season in Cayman Islands runs through January, May and October. May is the most popular month and a good time to visit if you want more to see and do.

  • March, June and September are the quietest months. March sees the lowest overall travel demand and is a good option if you want to keep things more relaxed.

Flights from Chicago to Cayman Islands: what to expect

  • When flying from Chicago, you can depart from Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW).

  • From Chicago, you can fly nonstop to at least one airport in Cayman Islands.

  • Roughly four direct flights connect Chicago with destinations around Cayman Islands every week.

  • The leading airlines operating this route include United and American Airlines.

  • George Town is one of the most popular routes from Chicago to Cayman Islands.

  • The average journey on this route comes in at around 4 hours 5 minutes.

Popular places to visit in Cayman Islands

George Town

  • One of the top destinations for Chicago to Cayman Islands flights, George Town heads up the list of places to visit. Kick off your sightseeing at standout attractions like Rum Point, Pedro St. James National Historic Site and The National Gallery of the Cayman Islands.

  • Owen Roberts International Airport (GCM) is George Town's main airport.

  • Explore the lineup of hotels in George Town and round out your trip with a stay that fits how you travel.

Cayman Brac

  • The biggest highlights in Cayman Brac include Skull Cave, The Bat's Cave and The Bluff.

  • Charles Kirkconnell International Airport (CYB) is the city's main airport.

  • The same magic behind our flight search can also help you find the best room rates online. Use it to compare prices and availability across hotels in Cayman Brac.

Little Cayman

  • East End lighthouse is a popular attraction to add to your plans in Little Cayman.

  • You can arrive in the city through its main airport, Edward Bodden Airport (LYB).

  • From short stays to longer trips, hotels in Little Cayman cover a wide range of travel styles and budgets.

Visiting Cayman Islands for the first time? Here's what you need to know

  • Entry rules can vary, so check whether you'll need a visa or any other types of documentation before you travel. Your travel agent, airline or the local consulate or embassy will have the most up-to-date information.

  • George Town is the capital of Cayman Islands, which has a population of roughly 75,000.

  • The same time is used throughout this destination, with one standard time zone fixed at UTC-5.

  • For a warmer trip to Cayman Islands, consider August.

  • Plan your trip for sometime around January if you prefer to be there when it's cooler.

  • October is usually the wettest time of year, while February is the driest.

  • Hoping to time your Chicago to Cayman Islands flight with a big occasion? Well-known events worth planning around include the Pirates Week Festival, Cayman Carnival Batabano and the Cayman Islands International Film Festival (CayFilm).

Complete your trip with hotels and a car rental

More travel options

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.