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
$415 - $599
Route
Depart
Return
Price
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 8/7
1 stop6h 18m
George Town Owen Roberts Intl
Wed 8/14
1 stop8h 39m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 8/7
1 stop6h 18m
George Town Owen Roberts Intl
Wed 8/14
2 stops9h 51m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 8/23
1 stop15h 19m
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
Fri 8/30
1 stop5h 30m
George Town Owen Roberts Intl
Thu 9/5
1 stop11h 09m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 8/30
2 stops15h 55m
George Town Owen Roberts Intl
Thu 9/5
2 stops18h 32m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 9/10
2 stops39h 55m
George Town Owen Roberts Intl
Sun 9/15
1 stop11h 09m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 6/15
1 stop20h 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
Thu 5/30
1 stop8h 35m
George Town Owen Roberts Intl
Thu 6/6
1 stop17h 06m
Chicago O'Hare IntlGeorge Town Owen Roberts Intl
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 6/15
Nonstop4h 02m
George Town Owen Roberts Intl
Tue 6/18
1 stop10h 33m
No data available for this route at this time. Please check back soon.
Boarding
Overall
Entertainment
Crew
Comfort
Food
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.
Boarding
Overall
Entertainment
Crew
Comfort
Food
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.
Boarding
Overall
Entertainment
Crew
Comfort
Food
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.
Boarding
Overall
Entertainment
Crew
Comfort
Food
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.
Boarding
Overall
Entertainment
Crew
Comfort
Food
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.
Boarding
Overall
Entertainment
Crew
Comfort
Food
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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