Find cheap flights from Madison to the Cayman Islands

Find cheap flights from Madison to the Cayman Islands

Search hundreds of travel sites at once for deals on flights to the Cayman Islands. Bundle your flight + hotel and save!

Round-trip
Economy
Madison (MSN)
Cayman Islands
Wed 10/20
Wed 10/27
Any month
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Top tips for finding cheap flights to the Cayman Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to the Cayman Islands is March.

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Top airlines flying Madison Truax Field to Cayman Islands

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,965 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Excellent crew."
Cons: "Gate agents were a little snippy."

Pros: "Fue un vuelo muy tranquilo y todos muy amables gracias!!"
Cons: "Muy cómodo el avión y el personal"

Pros: "Crew was great, comfort+ definitely has more leg room."
Cons: "Beer not guaranteed on flight for Delta comfort plus."

Pros: "Everyone was great."
Cons: "Nothing"

Pros: "Boarding was a fast and smooth process. Flight attendants were there to help with carry on luggage if needed. Always nice and do their best."

Pros: "Entertainment selection was nice."

Pros: "Good service great aircraft"
Cons: "Takes along time to get off airplane with everyone getting their bags from the overhead bins"

Pros: "Nobody was amazing. First Class Crew didn’t really care and there were only 6 of us up there."
Cons: "I was offered one during. They didn’t have spicy Bloody Mary mix. Tired to pass off a drink with plain tomato juice which was horrible. When my wife sent it back they didn’t offer her anything else."

Pros: "We got home safely! The crew was great and generally cheerful despite less than great conditions."
Cons: "Lots of delays due to weather, which I get. The plane was small and old and stuffy with too close seats."

Cons: "Seem that they turned off the air conditioning once we landed in the cabin got on the warm side."

Pros: "The flight attendant from IAD to MSP called Bernadette was wonderful!"

Cons: "There was barely any room on my seat and in front. It was the worst flight experience I’ve ever had, and I’ve flown on a fair bit of airlines from 3rd world countries."

Cons: "Change the movies more ofti"

Pros: "Attendant was friendly and efficient."
Cons: "No beverages or snacks."

Pros: "The service on plane was great and so was the opportunity to check luggage, although I was happy I didn't have to."
Cons: "Boarding from DTW to LAX, we had to stand for a long time on the jetway and it was really cold. It was the holding place after they checked my ticket. Otherwise, it was a great experience flying Delta."

Pros: "Flight was very late- about 45 minutes because of some problem with the "paperwork" they said. It was a beautiful day and the crew was ready to go, but we all sat for a long time before being allowed to leave Madison. It's especially bad when we've all made ourselves arrive at 5am for a 6am flight"
Cons: "on time departure"

Cons: "No room to move very cramped"

Pros: "Overall good experience"
Cons: "Plane 1hr late taking off"

Pros: "Friendly crew"
Cons: "Not enough leg room in seat"

Pros: "I did get home eventually"
Cons: "Flight was delayed. Seats are cramped."

Pros: "All the movie choices. Wish TVs came in all aircraft and/or flights 2+ hours. :-)"

Pros: "The flight itself was fine, boarded on time and arrived on time."
Cons: "A pet peeve of mine is having to check my carry on. They said the overhead bins were all completely full, so I checked my bag at the gate. Come to find out, there were a few spaces left and it wasn't necessary. Really annoying."

Pros: "Everything went as planned!"

Pros: "Enjoyed the ease of check in the spacious gate and the cleanliness of the planes cabin"
Cons: "No complaints"

Pros: "On time"
Cons: "Take a long time to taxi to the gate & getting off the plane."

Pros: "Plane was on time."
Cons: "My seat assignment was in the last row of the plan when the plane was not full"

Pros: "Nice crew, no delays"

Pros: "I love Delta, especially their newer planes that have screens in the backs of headrests and free movies."
Cons: "Leg room is never enough. I'm 6'1"."

Cons: "Seats are so tight so uncomfortable"

Cons: "3.5 hours late."

Pros: "Got me where I needed to go at the price I wanted to pay. - The gals at the ticketing desk were extremely helpful and cheerful."
Cons: "Not my typical Delta experience: -Boarding for special needs was a joke. A literal ‘run-on-sentence’. No more did I get up and they went to the next group. I was almost knocked over in the rush. -The onboard staff was nice enough. However, between the two of them, one of them had a thick accent. Maybe that one shouldn’t be the one making all on board announcements… and please fix the horrendous crackles too!!! -It seemed our pilot was in training… during our short flight a series of right and left turns were made, no effort to avoid turbulence, and the landing was surprisingly hard. It felt as if my spine took a quick jab to my brain as a result! What’s up?"

Pros: "Got me where I needed to go at the price I wanted to pay. - The gals at the ticketing desk were extremely helpful and cheerful."
Cons: "Not my typical Delta experience: -Boarding for special needs was a joke. A literal ‘run-on-sentence’. No more did I get up and they went to the next group. I was almost knocked over in the rush. -The onboard staff was nice enough. However, between the two of them, one of them had a thick accent. Maybe that one shouldn’t be the one making all on board announcements… and please fix the horrendous crackles too!!! -It seemed our pilot was in training… during our short flight a series of right and left turns were made, no effort to avoid turbulence, and the landing was surprisingly hard. It felt as if my spine took a quick jab to my brain as a result! What’s up?"

Cons: "They charged $300 for 3 bags"

Pros: "Flight was on time, boarded quickly and efficiently. Staff were nice enough but all business."

Pros: "On time flight"
Cons: "Cramped seating in coach. Think comfort not profit"

Pros: "So many movies to watch. Keep it up!"
Cons: "The food was too sweet and salty."

Cons: "Wifi didn't work (network wouldn't show up)."

Pros: "None"
Cons: "Delays"

Pros: "I always feel that the flight attendants on Delta truly care about your flight experience. The smile, the attentiveness, the thoroughness and giving you the attention you desire."
Cons: "Ran out of bananas before they got to me, no big deal and it looks like Delta is getting healthier options every year."

Pros: "Who could ask for more?"
Cons: "N/A"

Pros: "Got us there on time. not much more can ask for on a short flight"
Cons: "Wish Delta offers more reasonable and available business class awards"

Pros: "For the first time in a ling time I felt if I dropped something I didn't have to kiss it goodbye. My knees and back didn't hurt by the end of the fight. I know longer felt like a sardines in a tin."

Pros: "Delta flight attendants ultimately removing the passenger."
Cons: "The man that called the mother and her son a "F***** b****"."

Pros: "Got lucky, and got an upgrade!"
Cons: "Good staff on the plane very sweet like. Actually arrived early. Thought we would get breakfast on the flight from Madison Wisconsin to New York City."

Cons: "Late taking off, and then unable to get to gate on arrival"

Cons: "delayed 2+ hours due to runway maintenance. You'd think those things would be better planned..."

Pros: "Turbulence didn't allow the beverage cart to serve passengers"

Pros: "Our stewardess in the economy cabin was probably one of the best we have ever encountered. She was very courteous and personable."

Pros: "Nice flight attendant."
Cons: "Both legs of the flight were delayed, requiring long stays on the tarmac."

"My flight was delayed over 30 minutes and almost missed next flight the staffing was so short"

"American Airlines customer service was extremely poor. They canceled our flights multiple times. Then put us on standby trying to get on flights instead of booking us on a confirmed flight to get us home. So flight after flight we kept our hopes up just to be disappointed and stuck from a connecting flight. We had never been to Dallas so we were sleeping on the floor at the airport waiting to get home."

"Communication and updates and leaving on time."

Pros: "The flight wasn't crowded so I had a whole row of seats to myself."
Cons: "A less starchy/high carbohydrate meal. More green veg."

Pros: "The crew members are friendly and efficient in getting people on and taking off. Even with flights being full in all segments, it was smooth and fast to get people on and sit down."

Pros: "All 4 legs of our flight were right on time, and the planes appeared to be clean."
Cons: "Paying first class fare buys a couple of additional inches of space, but nothing more. There's nothing really first class about it."

Pros: "Crew members were okay"
Cons: "Wifi could be better"

Cons: "I’m tall. And there is no room to put my legs or my arms."

Pros: "Very friendly and accommodating."
Cons: "tv screens on the back of seats"

Cons: "Faster baggage pickup at DFW"

Cons: "Maintenance issues which led to a flight delay- understandable But we have been on the plane waiting to taxi. The person talking said it will take “3-4 minutes” to deplane...it’s taken about 45 min... Don’t overpromise and under deliver"

Pros: "Crew, seats, and smoothness of ride."
Cons: "You have to pay for seats to sit with your travel partner."

Cons: "Entertainment didn't work neither did the flight attendants. They sat in the back and quite literally did nothing, no juice and water. Worst service ever. I'll fly Delta from now on. American what happened to you?"

Pros: "The crew on the plane were great but even better was the women at the counter in terminal. She was amazing at getting everyone rerouted to their destinations"
Cons: "The WiFi was broken. the plane needed to be inspected and it took 2 attempts to get paperwork right and there was no inspector on the ground. 3 hours later after sitting on the plane for an hour with no food or drinks. If people have waited that long for one of your flights, give them a little food"

Pros: "The crew was fantastic and very nicely got us into an earlier flight and allowed my wife and I to sit together for our 10th anniversary"
Cons: "The entertainment apps were difficult to use"

Pros: "Everything was good!"

Pros: "WiFi entertainment system."
Cons: "Hard seats, no arm padding. No power to recharge phone and iPad."

Pros: "The flight attendant gave me a whole can of Diet Coke (I didn’t ask for it)"
Cons: "Seat number is crazy. ACDF. How about ABCD..."

Pros: "I paid for 2 seats and they took my seat and did not reimburse me"
Cons: "They should of reimbursed me for my seat that they took"

Cons: "Seats are small but I understand why just dont like it."

Pros: "Price for a very short notice trip, ease of online booking, very informative staff. Also, able to readjust my seating assignment."
Cons: "Unfortunately, the pilot assigned had a car wreck coming to work that morning. The delay was not bad, but my timeline was tight. Still, very grateful that a suitable replacement was found. The delay could have been much worse."

Pros: "Very nice crew!"

Pros: "The entertainment system is pretty cool and complete. There seems to be more room on coach."
Cons: "The usb charger for my seat didn't work. The power cord kept falling off."

Pros: "Nothing"
Cons: "My flight from Madison to Chicago got cancelled and I had to drive for three hors to get to o’ Hare."

Cons: "Get the plane to terminal bridge and not buss the passengers to and from to plane."

Pros: "Starters, the flight was co coached with American airlines which is one of the worst airlines I've traveled so far. They lost my bad, and so far no one can help me locate it. Changed my flight without noticing me, made me run around the airport like crazy trying to catch the connecting flight just to find out that AA airlines already changed my itinerary."
Cons: "Everything. Poor service, rude flight attendants, unhelpful staff."

Pros: "The food and the snack was pretty good"
Cons: "I paid $20 for the 24 hours of Wi-Fi and it never worked On either flight. The guy sitting in the seat behind me kept putting his knees into the back of the seat to prevent me from reclining so that his girlfriend could sleep with her head in his lap, so I could not recline in sleep on the long flight from Munich to Philadelphia. I don't have any of these issues when I fly on United. If you want me to fly on American more than I suggest you fixed them."

Cons: "This was a connecting flight, and I arrived at the gate from American Airlines flight 2656 in plenty of time to make the connection. However 15 minutes after arriving at my designated gate it was announced that American Airline flight 4874 would be delayed for 15 minutes for maintenance, which was fine, I want the plane I am flying in to be in perfect working order. So the departure time went from 2:32 to 3:00, then it went from 3:00 to 4:01. Next, it was announced that there had been a gate change. Once we all arrived and the passengers had deplaned and it was announced we could board it was closing in on 4:30. Now once we were on the plane we sat for one and a half hours with no food or water. Finally, they announced that the flight attendant would be coming around with water which was poured from bottles into cups and cookies or pretzels, what, did the plane crash on a deserted island and I not know it? After more sitting, we finally took off, I arrived at my destination 4 hours later than planned. I think this could have been handled more efficiently, and with more aplomb than the standard "we apologize", that does nothing for me and my trip went from 1 hour to 4 with me finally arriving at the Roanoke airport at 6:45."

Pros: "Flight was okay"
Cons: "That I ended up having to deal with AA for everything"

Pros: "We got to our destination aver 12 hours late."
Cons: "In addition to being rebooked approximately 12 hours after our original flight, this flight left about 40 minutes late."

Pros: "The staff was impressive with how friendly and welcoming they were! Everything went smoothly and I am a happy passenger!"

Pros: "Arrived slightly early. The crew was efficient and friendly. The interior and seats looked new."
Cons: "Nothing was negative."

Pros: "I took American's first direct flight between Philadelphia and San Antonio. It was a nice plane, good service, and amenities for a cost. Love that the plane had plugs!"

Cons: "Coach seating is too tight"

Cons: "Boarding chaos at Miami airport."

Pros: "I didn't make the flight due to a delay/cancellation."
Cons: "I missed this flight."

Pros: "Flight was moved from Philadelphia to Dalllas...no problem"
Cons: "scanty food from Dallas to Porltand"

Pros: "Nothing, even boarded front to back how idiotic have thet ever heard of back to front so you aren't waiting on everyone"
Cons: "Entertainment awful thought I was back in the 90's only overhead movies. Couldn't INDEPENDENTLY choose movies on a transatlantic flight are you kidding me. Sat behind huge guy who reclined his seat all the way back. When meal was served the my lap tray was hitting my knees and couldn't fit a can on tray without hitting his seat when I mentioned to flight attendants they did absolutely nothing"

Pros: "Left and arrived on time. Crew was friendly and professional."
Cons: "Passengers are packed in like sardines. All carry on bags must be checked at the gate as the overhead bins are too small to accommodate anything except a small personal bag or jacket."

Cons: "That fact that on both ways they changed our flights which either we got to the destination late or we had to run across the airport so we don't miss our flights"

Pros: "Boarding was simple"
Cons: "For my whole three hour flight a child kicked my chair, i asked the mother politely if she could get her to stop. the woman didn't even apologize and the kicking continued for three hours."

Cons: "The crew really seemed like they didn't like their job, and didn't want to be there. I felt kind of bad for them, nobody should be stuck in a job they hate."

Pros: "Fabulous crew and service, absolutely fantastic."
Cons: "Having to get off!"

Cons: "Ticketing agent was rude"

Cons: "Almost did NOT make it home to Salisbury airport. 3 hr layover in Philadelphia. Tried to obtain seat assignment 1 1/2 hrs prior to departure and was only told it was too soon and they would call my name. 5 minutes prior to boarding, checked again and told by another airport helper that the flight was OVERBOOKED and now I was on STANDBY. Purchased tickets over a month and a half ago. No problems getting to Orlando but to return to this- UNACCEPTABLE. DO NOT OVERBOOK a flight!!!!!!!! People make plans, have to work the following day and face the chance of not making it home-POOR CUSTOMER SERVICE!!!!!!! Thankfully 5 people did not show for the flight, should NOT gamble with that!!!!!!!"

Pros: "Almost always on time, captain keeps us updated, friendly airline staff"
Cons: "Nothing"

Pros: "Entertainment was free."
Cons: "Had to wait for mechanical issues so we were delayed."

Pros: "The flight was on time. It was serviced well by very friendly flight attendants. I enjoyed it very much."

Pros: "Boarding was smooth. Flight was on time. Some weather en route but pilot was able to avoid the turbulence. Overall a good flight."
Cons: "Unrelated to the flight- but immigration and customs in Grand Cayman was slow. 200+ people arrived on this plane and there ware 4 immigration agents although they had more stations. We spent about a half hour in line in each- immigration and then customs. Rental cars is another situation to be aware of regarding insurance."

Pros: "The flight was smooth and the service was great. Clean plane wonderful crew. We left our gate 10 early, and landed 30 minutes before our estimated time."
Cons: "It was not AA fault, but since we arrived so early we waited more than an hour for a new gate. Ours was occupied by a cancelled flight because something was wrong with the plane and couldn't move it."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Madison to the Cayman Islands

Airlines flying from Madison to the Cayman Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Madison to the Cayman Islands

Mandatory masks

Masks required on board, masks provided on flights from Madison to the Cayman Islands

Social distancing seating

Middle seats unavailable to book on flights from Madison to the Cayman Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Madison to the Cayman Islands

Book cheap flights from Madison to Cayman Islands

Recent round-trip flight deals

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