Our data shows that November tends to be the cheapest month to fly to Chicago from Grand Cayman. Users have commonly found prices around $586 for the month, but tickets can be as low as $373. Due to multiple factors, prepare for potentially higher prices in March.
When flying from Grand Cayman to Chicago, 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
$409 - $674
Route
Depart
Return
Price
George Town Owen Roberts IntlChicago O'Hare Intl
GCM - ORD
GCMORD
George Town Owen Roberts Intl
vie. 8/2
1 stop8h 22m
Chicago O'Hare Intl
lun. 8/5
1 stop5h 30m
George Town Owen Roberts IntlChicago O'Hare Intl
GCM - ORD
GCMORD
George Town Owen Roberts Intl
vie. 8/2
2 stops20h 42m
Chicago O'Hare Intl
lun. 8/5
2 stops27h 20m
George Town Owen Roberts IntlChicago O'Hare Intl
GCM - ORD
GCMORD
George Town Owen Roberts Intl
vie. 8/2
1 stop28h 49m
Chicago O'Hare Intl
lun. 8/5
1 stop28h 45m
George Town Owen Roberts IntlChicago Midway
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
vie. 8/2
2 stops19h 48m
Chicago Midway
lun. 8/5
1 stop5h 30m
George Town Owen Roberts IntlChicago Midway
GCM - MDW
GCMMDW
George Town Owen Roberts Intl
vie. 8/2
2 stops19h 48m
Chicago Midway
lun. 8/5
1 stop5h 30m
No data available for this route at this time. Please check back soon.
Food
Crew
Entertainment
Overall
Comfort
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Crew
Entertainment
Overall
Comfort
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Crew
Entertainment
Overall
Comfort
Boarding
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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