
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $245 (Expedia) |
One-way from | $95 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $803 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Mon 1/12
3:01 pm-4:05 pm
1 stop24h 04m
George Town Owen Roberts Intl
Sat 1/17
2:34 pm-8:03 am
2 stops18h 29m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Thu 3/5
6:30 am-9:15 pm
1 stop13h 45m
George Town Owen Roberts Intl
Mon 3/9
7:00 am-3:33 pm
1 stop8h 33m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 3/13
8:00 am-10:05 pm
1 stop14h 05m
George Town Owen Roberts Intl
Thu 3/19
7:00 am-3:33 pm
1 stop8h 33m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Wed 12/31
5:05 am-12:35 pm
1 stop6h 30m
George Town Owen Roberts Intl
Thu 1/8
1:50 pm-10:05 pm
2 stops9h 15m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 12/31
8:45 am-1:45 pm
Nonstop4h 00m
George Town Owen Roberts Intl
Thu 1/8
2:50 pm-6:04 pm
Nonstop4h 14m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 3/25
7:35 am-3:30 pm
1 stop7h 55m
George Town Owen Roberts Intl
Wed 4/1
1:50 pm-6:13 pm
Nonstop4h 23m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Fri 1/30
5:00 am-12:55 pm
1 stop6h 55m
George Town Owen Roberts Intl
Mon 2/2
1:50 pm-9:00 pm
1 stop8h 10m
ChicagoGeorge Town
MDW - GCM
MDWGCM
Chicago Midway
Sun 5/3
5:05 am-11:55 am
1 stop6h 50m
George Town Owen Roberts Intl
Sat 5/9
1:15 pm-8:25 pm
1 stop7h 10m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 12/24
5:30 am-2:27 pm
1 stop7h 57m
George Town Owen Roberts Intl
Wed 12/31
1:52 pm-12:02 am
1 stop11h 10m
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 4/26
6:00 am-11:24 am
1 stop5h 24m
George Town Owen Roberts Intl
Wed 4/29
12:45 pm-11:55 pm
1 stop11h 10m
Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $339). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $650). 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.
A simple way to save on the total cost of your ticket is to fly from Chicago to Grand Cayman at noon. If you’re flexible enough to do this you can expect to save up to 40% on your trip compared to booking a flight in the morning.
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
Crew
Food
Comfort
Overall
Boarding
Entertainment
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$697 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$467 | Average$720 | FlexibilityNo cancel fee | On-time71% |