Fly from
Fly to
Route
Depart
Return
Price
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Wed 2/19
7:25 am-4:10 pm
1 stop7h 45m
George Town Owen Roberts Intl
Fri 2/28
4:45 pm-8:44 am
1 stop16h 59m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 1/10
1:34 pm-9:20 pm
1 stop6h 46m
George Town Owen Roberts Intl
Fri 1/17
4:45 pm-12:29 pm
1 stop20h 44m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Tue 2/25
5:45 am-12:55 pm
1 stop6h 10m
George Town Owen Roberts Intl
Sat 3/1
2:10 pm-11:15 pm
2 stops10h 05m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 3/18
8:48 am-12:45 pm
Nonstop3h 57m
George Town Owen Roberts Intl
Tue 3/25
1:50 pm-6:06 pm
Nonstop4h 16m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 2/23
6:00 am-12:44 pm
1 stop5h 44m
George Town Owen Roberts Intl
Fri 2/28
2:09 pm-10:20 pm
1 stop9h 11m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 2/1
6:30 pm-12:35 pm
1 stop17h 05m
George Town Owen Roberts Intl
Wed 2/5
3:15 pm-9:53 pm
1 stop7h 38m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 2/22
7:05 am-2:04 pm
1 stop5h 59m
George Town Owen Roberts Intl
Wed 2/26
2:09 pm-11:59 pm
1 stop10h 50m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 12/5
7:19 am-1:40 pm
1 stop29h 21m
George Town Owen Roberts Intl
Sun 12/8
4:00 pm-7:32 pm
1 stop28h 32m
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
Sun 12/22
8:25 pm-5:50 pm
2 stops20h 25m
Cayman Brac Gerrard-Smith
Sat 12/28
3:40 pm-8:57 am
2 stops42h 17m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 1/5
11:48 am-1:49 pm
2 stops25h 01m
George Town Owen Roberts Intl
Sun 1/12
2:50 pm-5:47 pm
2 stops27h 57m
Currently, January is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $467). Flying from Chicago to Cayman Islands in June is currently the most expensive (average of $560). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
When flying from Chicago 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.
Entertainment
Crew
Food
Boarding
Overall
Comfort
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Entertainment
Crew
Food
Boarding
Overall
Comfort
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Entertainment
Crew
Food
Boarding
Overall
Comfort
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Entertainment
Crew
Food
Boarding
Overall
Comfort
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Entertainment
Crew
Food
Boarding
Overall
Comfort
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Entertainment
Crew
Food
Boarding
Overall
Comfort
Reviews
Great service throughout our flight. Easy boarding with early bird check in
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Delta | Cheapest$348 | Average$476 | FlexibilityNo cancel fee | On-timeN/A |
American Airlines | Cheapest$368 | Average$606 | FlexibilityNo cancel fee | On-time71% |
United Airlines | Cheapest$420 | Average$671 | FlexibilityNo cancel fee | On-time69% |