Find a great deal and save up to 50% by booking at least 34 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Cayman Islands within the next two weeks, with the cheapest ticket starting at $655.
January is one of the best times of the year to fly to Cayman Islands from Chicago. Prices for January average $629 per person but you can even find prices for as low as $230. The most expensive prices can be found in the month of December. Opting for a January flight can save you 41% on your journey compared to booking in December
When flying from Chicago to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$419 - $603
Route
Depart
Return
Price
Chicago MidwayGeorge Town Owen Roberts Intl
MDW - GCM
MDWGCM
Chicago Midway
Wed 5/15
1 stop26h 03m
George Town Owen Roberts Intl
Wed 5/22
1 stop6h 57m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 5/15
1 stop24h 05m
George Town Owen Roberts Intl
Wed 5/22
1 stop7h 07m
Chicago MidwayGeorge Town Owen Roberts Intl
MDW - GCM
MDWGCM
Chicago Midway
Mon 4/29
2 stops33h 15m
George Town Owen Roberts Intl
Wed 5/1
1 stop6h 57m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 5/15
2 stops23h 55m
George Town Owen Roberts Intl
Wed 5/22
1 stop7h 07m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 5/9
1 stop8h 35m
George Town Owen Roberts Intl
Sun 5/12
1 stop18h 09m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 5/9
1 stop8h 35m
George Town Owen Roberts Intl
Sun 5/12
2 stops18h 21m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 6/12
1 stop6h 09m
George Town Owen Roberts Intl
Tue 6/18
1 stop6h 50m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 6/11
1 stop15h 50m
George Town Owen Roberts Intl
Sun 6/16
Nonstop4h 10m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 5/13
1 stop14h 41m
George Town Owen Roberts Intl
Sun 5/26
1 stop11h 04m
No data available for this route at this time. Please check back soon.
Food
Overall
Boarding
Crew
Comfort
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Food
Overall
Boarding
Crew
Comfort
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Food
Overall
Boarding
Crew
Comfort
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Food
Overall
Boarding
Crew
Comfort
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Food
Overall
Boarding
Crew
Comfort
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Food
Overall
Boarding
Crew
Comfort
Entertainment
Reviews
I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!
Cheapflights makes it easy to find Chicago to Cayman Islands flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Cayman Islands from Chicago.
Certainly. Search results for flights to Cayman Islands from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Yes, Cheapflights offers price alerts on Chicago to Cayman Islands flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.