Travelers have found it’s best to book a flight 22 days in advance to save up to 81% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 22 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago O'Hare Intl Airport to Cayman Islands 1-2 weeks in advance for as low as $671, or $671 for flights within the next 24 hours.
October is one of the best times of the year to fly to Cayman Islands from Chicago O'Hare Intl Airport. Prices for October average $578 per person but you can even find prices for as low as $380. The most expensive prices can be found in the month of December. Opting for a October flight can save you 22% on your journey compared to booking in December
When flying from Chicago O'Hare Intl Airport 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
$418 - $614
Route
Depart
Return
Price
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
Tue 6/18
1 stop19h 20m
George Town Owen Roberts Intl
Mon 6/24
1 stop22h 51m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 5/29
1 stop24h 20m
George Town Owen Roberts Intl
Sat 6/1
1 stop11h 22m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 6/13
1 stop10h 53m
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 stop22h 35m
George Town Owen Roberts Intl
Sun 6/2
2 stops16h 15m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 7/25
1 stop8h 35m
George Town Owen Roberts Intl
Thu 8/8
2 stops16h 07m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 8/31
2 stops14h 29m
George Town Owen Roberts Intl
Sat 9/7
2 stops10h 16m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 6/15
2 stops17h 50m
George Town Owen Roberts Intl
Tue 6/18
2 stops18h 37m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 6/29
Nonstop4h 02m
George Town Owen Roberts Intl
Sat 7/6
Nonstop4h 12m
No data available for this route at this time. Please check back soon.
Entertainment
Overall
Food
Comfort
Boarding
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
Overall
Food
Comfort
Boarding
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
Overall
Food
Comfort
Boarding
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
Overall
Food
Comfort
Boarding
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
Overall
Food
Comfort
Boarding
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
Overall
Food
Comfort
Boarding
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.
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