When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 22 days in advance, which can save you up to 81% on flights from Illinois to Cayman Islands compared to booking the week you need them. Waiting 22 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $671. For sooner than that we have options available in the next 3 days from $671.
Due to multiple factors, expect to potentially pay more when booking in December. For low rates, October can be a great choice for travel to Cayman Islands. Flights to Cayman Islands from Illinois in October are about $577 on average during October, but can be found for as low as $380.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Cayman Islands as you normally would.
Fly from
Fly to
Budget
$418 - $593
Route
Depart
Return
Price
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 5/28
1 stop18h 55m
George Town Owen Roberts Intl
Fri 5/31
1 stop26h 48m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 6/11
1 stop19h 20m
George Town Owen Roberts Intl
Tue 6/18
1 stop20h 51m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 5/29
1 stop24h 05m
George Town Owen Roberts Intl
Sun 6/2
1 stop18h 55m
Lambert-St LouisGeorge Town Owen Roberts Intl
STL - GCM
STLGCM
Lambert-St Louis
Sat 9/28
2 stops20h 23m
George Town Owen Roberts Intl
Sat 10/12
2 stops18h 46m
Lambert-St LouisGeorge Town Owen Roberts Intl
STL - GCM
STLGCM
Lambert-St Louis
Sat 9/28
2 stops20h 23m
George Town Owen Roberts Intl
Sat 10/12
1 stop17h 15m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 6/9
1 stop8h 35m
George Town Owen Roberts Intl
Sun 6/16
1 stop18h 09m
Lambert-St LouisGeorge Town Owen Roberts Intl
STL - GCM
STLGCM
Lambert-St Louis
Fri 5/17
1 stop5h 26m
George Town Owen Roberts Intl
Fri 5/24
1 stop10h 49m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 6/13
1 stop8h 35m
George Town Owen Roberts Intl
Sun 6/16
1 stop18h 09m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 6/11
1 stop16h 45m
George Town Owen Roberts Intl
Sun 6/16
Nonstop4h 10m
No data available for this route at this time. Please check back soon.
Overall
Boarding
Comfort
Food
Crew
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Boarding
Comfort
Food
Crew
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Boarding
Comfort
Food
Crew
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Boarding
Comfort
Food
Crew
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Boarding
Comfort
Food
Crew
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Overall
Boarding
Comfort
Food
Crew
Entertainment
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
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Certainly. Search results for flights to Cayman Islands from Illinois shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
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