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 $579 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
$343 - $669
Route
Depart
Return
Price
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 9/21
1 stop16h 46m
George Town Owen Roberts Intl
Wed 9/25
1 stop8h 43m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 8/23
1 stop17h 55m
George Town Owen Roberts Intl
Wed 8/28
1 stop11h 11m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 9/19
1 stop15h 35m
George Town Owen Roberts Intl
Thu 9/26
1 stop11h 09m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 9/21
1 stop16h 46m
George Town Owen Roberts Intl
Wed 9/25
2 stops10h 16m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 9/19
2 stops26h 35m
George Town Owen Roberts Intl
Sun 9/29
1 stop8h 14m
Chicago MidwayGeorge Town Owen Roberts Intl
MDW - GCM
MDWGCM
Chicago Midway
Sat 9/28
2 stops25h 55m
George Town Owen Roberts Intl
Mon 10/7
1 stop8h 54m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 9/24
1 stop8h 43m
George Town Owen Roberts Intl
Sat 9/28
1 stop6h 44m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 6/6
1 stop8h 35m
George Town Owen Roberts Intl
Thu 6/13
1 stop21h 09m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 7/14
Nonstop4h 02m
George Town Owen Roberts Intl
Sat 7/20
Nonstop4h 12m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Food
Boarding
Overall
Crew
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.
Entertainment
Comfort
Food
Boarding
Overall
Crew
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.
Entertainment
Comfort
Food
Boarding
Overall
Crew
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.
Entertainment
Comfort
Food
Boarding
Overall
Crew
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.
Entertainment
Comfort
Food
Boarding
Overall
Crew
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.
Entertainment
Comfort
Food
Boarding
Overall
Crew
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.
0%of flight departures | Early morningMidnight to 6 am |
---|---|
100%of flight departures | Morning6 am to noon |
0%of flight departures | AfternoonNoon to 6 pm |
0%of flight departures | Evening6 pm to midnight |
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