App
Customer Support
EUR
Find Bookings
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Cheap flight deals from Madison to Grand Cayman Starting at €292

Discover our range of affordable one-way and round-trip flights from Madison to Grand Cayman and kick-start your next adventure today!

  • One way
  • Round-trip
      • MSN05:45
        5h 53m
        1 stop
        GCM11:38
        Mon, Mar 17|Madison - Grand Cayman|Delta Air Lines
        €292€1,001
        71% OFF
        71% OFF
        €1,001€292

        Choose Delta Air Lines flights from Madison to Grand Cayman. The one-way connecting flight with Delta Air Lines departs from Dane County Regional Airport on Mon, Mar 17, arriving at Owen Roberts International Airport. One-way Prices start from €292 including taxes and charges.

      • MSN05:45
        5h 53m
        1 stop
        GCM11:38
        Sun, Mar 16|Madison - Grand Cayman|Delta Air Lines
        €401€1,001
        60% OFF
        60% OFF
        €1,001€401

        Choose Delta Air Lines flights from Madison to Grand Cayman. The one-way connecting flight with Delta Air Lines departs from Dane County Regional Airport on Sun, Mar 16, arriving at Owen Roberts International Airport. One-way Prices start from €401 including taxes and charges.

      • MSN16:15
        21h 45m
        1 stop
        GCM14:00
        Sat, Mar 22|Madison - Grand Cayman|American Airlines
        €525€1,001
        48% OFF
        48% OFF
        €1,001€525

        Choose American Airlines flights from Madison to Grand Cayman. The one-way connecting flight with American Airlines departs from Dane County Regional Airport on Sat, Mar 22, arriving at Owen Roberts International Airport. One-way Prices start from €525 including taxes and charges.

      • MSN05:45
        5h 53m
        1 stop
        GCM11:38
        Fri, Mar 21|Madison - Grand Cayman|Delta Air Lines
        €841
        €841

        Choose Delta Air Lines flights from Madison to Grand Cayman. The one-way connecting flight with Delta Air Lines departs from Dane County Regional Airport on Fri, Mar 21, arriving at Owen Roberts International Airport. One-way Prices start from €841 including taxes and charges.

      • MSN01:00 pm
        3h 5m
        Nonstop
        GCM02:00 pm
        Fri, Feb 21|Madison - Grand Cayman|Delta Air Lines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Madison to Grand Cayman flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL1160

    Delta Air Lines

    05:45

    MSN

    2.2h

    08:57

    ATL

    SMTWTFS
    Search

  2. DL600

    Delta Air Lines

    09:55

    ATL

    2.7h

    12:38

    GCM

    SMTWTFS

  3. AA1002

    American Airlines

    06:13

    MSN

    2.2h

    09:25

    CLT

    SMTWTFS
    Search

  4. AA3057

    American Airlines

    11:00

    CLT

    2.4h

    13:21

    MIA

    SMTWTFS

  5. AA956

    American Airlines

    12:05

    MIA

    1.8h

    13:55

    GCM

    SMTWTFS

  6. AA1002

    American Airlines

    06:13

    MSN

    2.2h

    09:25

    CLT

    SMTWTFS
    Search

  7. AA350

    American Airlines

    11:25

    CLT

    2.8h

    13:15

    GCM

    SMTWTFS

  8. UA4437

    United Airlines

    13:04

    MSN

    1.3h

    14:20

    ORD

    SMTWTFS
    Search

  9. UA1633

    United Airlines

    21:40

    ORD

    2.1h

    00:45

    EWR

    SMTWTFS

  10. UA2119

    United Airlines

    09:34

    EWR

    4.0h

    12:35

    GCM

    SMTWTFS

  11. UA5732

    United Airlines

    13:05

    MSN

    1.1h

    14:13

    ORD

    SMTWT-S
    Search

  12. UA1633

    United Airlines

    21:40

    ORD

    2.1h

    00:45

    EWR

    SMTWTFS

  13. UA2119

    United Airlines

    09:34

    EWR

    4.0h

    12:35

    GCM

    SMTWTFS

  14. UA5299

    United Airlines

    15:42

    MSN

    1.1h

    16:48

    ORD

    -----FS
    Search

  15. UA1633

    United Airlines

    21:40

    ORD

    2.1h

    00:45

    EWR

    SMTWTFS

  16. UA2119

    United Airlines

    09:34

    EWR

    4.0h

    12:35

    GCM

    SMTWTFS

  17. UA5299

    United Airlines

    15:42

    MSN

    1.1h

    16:48

    ORD

    -----FS
    Search

  18. UA534

    United Airlines

    18:11

    ORD

    2.3h

    21:28

    EWR

    SMTWTFS

  19. UA2119

    United Airlines

    09:34

    EWR

    4.0h

    12:35

    GCM

    SMTWTFS

  20. UA4574

    United Airlines

    17:16

    MSN

    1.1h

    18:25

    ORD

    SMTWTF-
    Search

  21. UA1023

    United Airlines

    21:05

    ORD

    1.9h

    23:57

    DCA

    SMTWTFS

  22. UA220

    United Airlines

    12:35

    IAD

    3.4h

    15:00

    GCM

    -----F-

  23. UA4574

    United Airlines

    17:16

    MSN

    1.1h

    18:25

    ORD

    SMTWTF-
    Search

  24. UA483

    United Airlines

    19:55

    ORD

    3.1h

    22:59

    IAH

    SMTWTFS

  25. UA753

    United Airlines

    12:40

    IAH

    2.9h

    15:35

    GCM

    -----F-

  26. UA4574

    United Airlines

    17:16

    MSN

    1.1h

    18:25

    ORD

    SMTWTF-
    Search

  27. UA1633

    United Airlines

    21:40

    ORD

    2.1h

    00:45

    EWR

    SMTWTFS

  28. UA2119

    United Airlines

    09:34

    EWR

    4.0h

    12:35

    GCM

    SMTWTFS
Find more flights and airlines

When is the cheapest time to fly from Madison to Grand Cayman?

These price trend charts carefully monitor and predict how flight prices from Madison to Grand Cayman will change. Keep a close eye on them to understand when the best time to buy your tickets is.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Madison (MSN) to Grand Cayman (GCM) the cheapest?

    Airlines adjust prices for flights from Madison to Grand Cayman based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Madison (MSN) to Grand Cayman (GCM) cost?

    According to Trip.com's data, the lowest price is around €942.

  • What is the transportation method from the main airport to downtown in Grand Cayman?

    • The distance from Owen Roberts International Airport to downtown is about 11 km, by taxi about 30 minutes.

  • How many airports are there in Grand Cayman (GCM)?

    There are 1 airport(s) near Grand Cayman (GCM): Owen Roberts International Airport.

How to find a cheap flight from Madison to Grand Cayman

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Madison to Grand Cayman

Cheapest direct flight price€292
Off-season for travelMarch
Peak season for travelFebruary
Flight distance2,754.86 km
Popular airlineAmerican Airlines

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.