$154 Cheap flight deals from Madison (MSN) to Grand Cayman (GCM)

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This Weekend's Flight Deals from Madison to Grand Cayman

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 2 - Wed, Jan 21
MSN
Dane County Regional
GCM
Owen Roberts Intl.
$579 Roundtrip, found 1 hour ago
$579
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Jan 2 from Dane County Regional to Owen Roberts Intl., returning Wed, Jan 21, priced at $579 found 1 hour ago

Airfares from $154 One Way, $412 Round Trip from Madison to Grand Cayman

Prices starting at $412 for return flights and $154 for one-way flights to Grand Cayman were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Feb 5 - Fri, Feb 6
MSN
Madison
GCM
Grand Cayman
$412 Roundtrip, found 13 hours ago
$412
Roundtrip
found 13 hours ago
Select United flight, departing Thu, Feb 5 from Madison to Grand Cayman, returning Fri, Feb 6, priced at $412 found 13 hours ago
Sat, Jan 31 - Fri, Feb 6
MSN
Madison
GCM
Grand Cayman
$414 Roundtrip, found 14 hours ago
$414
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Jan 31 from Madison to Grand Cayman, returning Fri, Feb 6, priced at $414 found 14 hours ago
Sun, Feb 1 - Fri, Feb 13
MSN
Madison
GCM
Grand Cayman
$417 Roundtrip, found 1 hour ago
$417
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, Feb 1 from Madison to Grand Cayman, returning Fri, Feb 13, priced at $417 found 1 hour ago
Wed, Feb 4 - Mon, Feb 9
MSN
Madison
GCM
Grand Cayman
$418 Roundtrip, found 1 day ago
$418
Roundtrip
found 1 day ago
Select United flight, departing Wed, Feb 4 from Madison to Grand Cayman, returning Mon, Feb 9, priced at $418 found 1 day ago
Tue, Feb 3 - Mon, Feb 9
MSN
Madison
GCM
Grand Cayman
$420 Roundtrip, found 13 hours ago
$420
Roundtrip
found 13 hours ago
Select United flight, departing Tue, Feb 3 from Madison to Grand Cayman, returning Mon, Feb 9, priced at $420 found 13 hours ago

Grand Cayman economy flight packages

Price found within the past 48 hours. Click for updated prices.
Point West
4.0-star property

Point West

No reviews

Jan 31 - Feb 7

7 night stay

Madison (MSN) to George Town (GCM)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,069, price is now $2,118 per person
$2,118
per person
found 23 hours ago
Hotel Indigo Grand Cayman by IHG
4.5-star property

Hotel Indigo Grand Cayman by IHG

9.8/10 Exceptional! (432 reviews)

Jan 31 - Feb 7

7 night stay

Madison (MSN) to George Town (GCM)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,478, price is now $2,660 per person
$2,660
per person
found 23 hours ago
The staff is excellent, especially Tarren who was truly amazing with resolving a few issues regarding our room. Tarren ungraded us to the one bedroom oceanfront suite (room #412) which we absolutely loved. It felt more like an apartment and had best view of the stunning grounds, the gorgeous pool and the ocean. We also enjoyed having the different choices of restaurants within the hotel itself. The beach bar is really special and the had one the best views of the seven mile beach. We visited the bar twice on stay. The things we did not like about our stay is the location of our original premium king ocean room. It is located on the left side of the building closer to the main road and across from the parking lot. We felt it was too noisy and couldn’t enjoy the sitting on the balcony. We also didn’t like that there was no grand lobby/common area. There is a receptionist area with wall partition and a small sitting area behind and separated area in the adjacent building for the guest elevators. We felt it was a little disjointed.

Reviewed on Aug 2, 2025

Club Suites at Rum Point
4.0-star property

Club Suites at Rum Point

9.6/10 Exceptional! (25 reviews)

Jan 31 - Feb 7

7 night stay

Madison (MSN) to George Town (GCM)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $6,514, price is now $5,011 per person
$5,011
per person
found 23 hours ago
Very relaxing property. Clean and comfortable. The unit was well stocked. Tons of towels and all the essential kitchen tools. Nice appliances and comfy beds. Staff was very friendly and helpful. We would definitely stay here again.

Reviewed on Jan 7, 2024

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More About Flying To Grand Cayman from Madison

Route Information for Flights from Madison to Grand Cayman

Origin Airport IATA Code
MSN
Destination Airport IATA Code
GCM
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Madison to Grand Cayman

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.