What airlines fly to Cayman Islands?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Cayman Islands from Wisconsin according to our data. American Airlines is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 3 different airlines that fly to Cayman Islands on a routine basis, so you have a few additional options to choose from.

How long is the flight from Wisconsin to Cayman Islands?

Flight times vary depending on what airport in Wisconsin you fly out of and what airport in Cayman Islands you fly into. For example, flying from Milwaukee to George Town takes 5h 25m on average. On the other hand, flying from Madison to George Town takes 5h 51m on average. Keep in mind that it’s always quicker to opt for a non-stop flight, so be sure to check momondo if there are any available for your route.

What is the cheapest airline that flies from Wisconsin to Cayman Islands?

Spirit Airlines, Delta, and United Airlines are the most popular carriers operating from Wisconsin to Cayman Islands

When did momondo last update prices for flights from Wisconsin to Cayman Islands?

Prices for flights from Wisconsin to Cayman Islands are refreshed on a daily basis.

How many operators does momondo search for flights from Wisconsin to Cayman Islands?

As of December 2025, there are 4 operators available to choose from for flights from Wisconsin to Cayman Islands.

How old do you have to be to fly from Wisconsin to Cayman Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Cayman Islands.

What documentation or ID do you need to fly to Cayman Islands?

The travel and health documents required for your trip to Cayman Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Cayman Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$72 Cheap Flights from Wisconsin to the Cayman Islands in 2025/26

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Find the cheapest flights from Wisconsin to the Cayman Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:15 am - 1:38 pm

ORD

GCM

7h 23m1 stop

2:34 pm - 10:03 pm

GCM

ORD

8h 29m1 stop

$247Spirit Airlines

Sat, Jan 24 - Sat, Jan 31

5:15 am - 1:38 pm

ORD

GCM

7h 23m1 stop

2:40 pm - 8:54 pm

GCM

ORD

7h 14m1 stop

$269Spirit Airlines

Sat, Feb 7 - Thu, Feb 12

12:00 pm - 1:53 pm

ORD

GCM

24h 53m1 stop

2:49 pm - 10:36 pm

GCM

ORD

8h 47m1 stop

$278Multiple Airlines

Sat, Jan 24 - Thu, Jan 29

12:00 pm - 1:53 pm

ORD

GCM

24h 53m1 stop

2:49 pm - 11:22 am

GCM

ORD

21h 33m1 stop

$286Multiple Airlines

Sat, Jan 24 - Sun, Feb 1

6:30 am - 12:45 pm

MSN

GCM

6h 15m1 stop

1:50 pm - 10:40 pm

GCM

MSN

8h 50m1 stop

$376United Airlines

Tue, Mar 24 - Mon, Mar 30

7:32 am - 8:20 pm

MKE

GCM

11h 48m2 stops

8:50 am - 10:49 pm

GCM

MKE

14h 59m1 stop

$381American Airlines

Tue, Jan 20 - Tue, Jan 27

9:30 am - 2:35 pm

MKE

GCM

28h 05m1 stop

8:50 am - 10:49 pm

GCM

MKE

14h 59m1 stop

$382American Airlines

Tue, Jan 20 - Tue, Jan 27

6:15 pm - 12:55 pm

MSP

GCM

17h 40m2 stops

1:50 pm - 9:50 pm

GCM

MSP

9h 00m2 stops

$451Southwest

Wed, Jan 21 - Wed, Jan 28

8:00 am - 4:00 pm

MKE

GCM

7h 00m1 stop

2:50 pm - 8:48 pm

GCM

MKE

6h 58m1 stop

$486United Airlines

Mon, Jan 5 - Thu, Jan 8

6:20 pm - 12:30 pm

MSP

GCM

17h 10m2 stops

1:50 pm - 9:50 pm

GCM

MSP

9h 00m2 stops

$487Southwest

Fri, Feb 6 - Tue, Feb 10

Spirit Airlines flights from Wisconsin to Cayman Islands

Our best Spirit Airlines deals on Wisconsin to Cayman Islands flight tickets

Spirit Airlines

Jan 24

ORD5:15 amChicago O'Hare Intl

7h 23m

1 stop

GCM1:38 pmGeorge Town Owen Roberts Intl

Jan 31

GCM2:34 pmGeorge Town Owen Roberts Intl

8h 29m

1 stop

ORD10:03 pmChicago O'Hare Intl

$247

Find similar

Spirit Airlines

Feb 7

ORD5:15 amChicago O'Hare Intl

7h 23m

1 stop

GCM1:38 pmGeorge Town Owen Roberts Intl

Feb 12

GCM2:40 pmGeorge Town Owen Roberts Intl

7h 14m

1 stop

ORD8:54 pmChicago O'Hare Intl

$269

Find similar

Spirit Airlines

Jan 24

ORD5:15 amChicago O'Hare Intl

7h 23m

1 stop

GCM1:38 pmGeorge Town Owen Roberts Intl

Jan 31

GCM2:34 pmGeorge Town Owen Roberts Intl

7h 29m

1 stop

ORD9:03 pmChicago O'Hare Intl

$289

Find similar

Southwest flights from Wisconsin to Cayman Islands

Our best Southwest deals on Wisconsin to Cayman Islands flight tickets

Southwest

Jan 21

MSP6:15 pmMinneapolis St Paul

17h 40m

2 stops

GCM12:55 pmGeorge Town Owen Roberts Intl

Jan 28

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 00m

2 stops

MSP9:50 pmMinneapolis St Paul

$451

Find similar

Southwest

Feb 6

MSP6:20 pmMinneapolis St Paul

17h 10m

2 stops

GCM12:30 pmGeorge Town Owen Roberts Intl

Feb 10

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 00m

2 stops

MSP9:50 pmMinneapolis St Paul

$487

Find similar

Southwest

Jan 9

MSP6:15 pmMinneapolis St Paul

17h 15m

2 stops

GCM12:30 pmGeorge Town Owen Roberts Intl

Jan 16

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 30m

2 stops

MSP10:20 pmMinneapolis St Paul

$507

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

5:15 am-1:38 pm

1 stop7h 23m

George Town Owen Roberts Intl

Sat 1/31

2:34 pm-10:03 pm

1 stop8h 29m

$247

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/7

5:15 am-1:38 pm

1 stop7h 23m

George Town Owen Roberts Intl

Thu 2/12

2:40 pm-8:54 pm

1 stop7h 14m

$269

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

12:00 pm-1:53 pm

1 stop24h 53m

George Town Owen Roberts Intl

Thu 1/29

2:49 pm-10:36 pm

1 stop8h 47m

$278

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

12:00 pm-1:53 pm

1 stop24h 53m

George Town Owen Roberts Intl

Sun 2/1

2:49 pm-11:22 am

1 stop21h 33m

$286

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Tue 3/24

6:30 am-12:45 pm

1 stop6h 15m

George Town Owen Roberts Intl

Mon 3/30

1:50 pm-10:40 pm

1 stop8h 50m

$376

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Tue 1/20

7:32 am-8:20 pm

2 stops11h 48m

George Town Owen Roberts Intl

Tue 1/27

8:50 am-10:49 pm

1 stop14h 59m

$381

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Tue 1/20

9:30 am-2:35 pm

1 stop28h 05m

George Town Owen Roberts Intl

Tue 1/27

8:50 am-10:49 pm

1 stop14h 59m

$382

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Wed 1/21

6:15 pm-12:55 pm

2 stops17h 40m

George Town Owen Roberts Intl

Wed 1/28

1:50 pm-9:50 pm

2 stops9h 00m

$451

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Mon 1/5

8:00 am-4:00 pm

1 stop7h 00m

George Town Owen Roberts Intl

Thu 1/8

2:50 pm-8:48 pm

1 stop6h 58m

$486

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Fri 2/6

6:20 pm-12:30 pm

2 stops17h 10m

George Town Owen Roberts Intl

Tue 2/10

1:50 pm-9:50 pm

2 stops9h 00m

$487

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Wisconsin to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of August, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $535.

What is the cheapest day to depart on your flight to Cayman Islands?

Our data shows that Tuesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $526. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Sunday is $742.

What is the cheapest time of day to depart on your flight to Cayman Islands?

According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Wisconsin to Cayman Islands in the afternoon for as low as $558. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $612 on average. Flights to Cayman Islands from Wisconsin in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

Can stopping save me money on Wisconsin to Cayman Islands flights?

You could potentially save up to 34% on your flight if you consider stops on a Wisconsin to Cayman Islands flight.

Cheap Wisconsin to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Cayman Islands

Fastest flight time	4h 00m
Direct flights	Every day
Airports in Cayman Islands	6 airports

The fastest flight from Wisconsin to Cayman Islands takes 4h 00m

Direct flights go from Wisconsin to Cayman Islands every day.

There are 6 airports in Cayman Islands. From Wisconsin there are direct flights to George Town Owen Roberts Intl (GCM).

Search flight deals

When did momondo last update prices for flights from Wisconsin to Cayman Islands?
Prices for flights from Wisconsin to Cayman Islands are refreshed on a daily basis.
How many operators does momondo search for flights from Wisconsin to Cayman Islands?
As of December 2025, there are 4 operators available to choose from for flights from Wisconsin to Cayman Islands.
How old do you have to be to fly from Wisconsin to Cayman Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Cayman Islands.
What documentation or ID do you need to fly to Cayman Islands?
The travel and health documents required for your trip to Cayman Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Cayman Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Wisconsin to Cayman Islands

Compare and see reviews for airlines that fly from Wisconsin to Cayman Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $212	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights
United Airlines	PriceFrom $315	Free Cancellation	Rating 7.4 9,095 reviews	Search United Airlines flights
American Airlines	PriceFrom $470	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Cayman Islands?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Cayman Islands from Wisconsin.

Can I find flights from Wisconsin to Cayman Islands with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Wisconsin to Cayman Islands flights to just show those with flexible booking policies.

How can momondo help me find flights from Wisconsin to Cayman Islands?

Once you have performed a search for Wisconsin to Cayman Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Wisconsin to Cayman Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Wisconsin to Cayman Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Popular cities in the Cayman Islands

Flights to George Townfrom $191

Flights to Cayman Bracfrom $304

Flights to Little Caymanfrom $328

Cheap flights from Wisconsin to the Cayman Islands from $72

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to the Cayman Islands departing on 2/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Wisconsin to the Cayman Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Wisconsin to Cayman Islands

Our best Spirit Airlines deals on Wisconsin to Cayman Islands flight tickets

Southwest flights from Wisconsin to Cayman Islands

Our best Southwest deals on Wisconsin to Cayman Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to the Cayman Islands that are best for you.

See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Wisconsin to Cayman Islands

What is the cheapest month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of August, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $535.

What is the cheapest day to depart on your flight to Cayman Islands?

What is the cheapest time of day to depart on your flight to Cayman Islands?

Can stopping save me money on Wisconsin to Cayman Islands flights?

You could potentially save up to 34% on your flight if you consider stops on a Wisconsin to Cayman Islands flight.

What is the cheapest airline that flies from Wisconsin to Cayman Islands?

Spirit Airlines, Delta, and United Airlines are the most popular carriers operating from Wisconsin to Cayman Islands

What airlines fly to Cayman Islands?

How long is the flight from Wisconsin to Cayman Islands?

Cheap Wisconsin to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Cayman Islands

Fastest flight time

Direct flights

Airports in Cayman Islands

When did momondo last update prices for flights from Wisconsin to Cayman Islands?

How many operators does momondo search for flights from Wisconsin to Cayman Islands?

How old do you have to be to fly from Wisconsin to Cayman Islands?

What documentation or ID do you need to fly to Cayman Islands?

Best airlines flying from Wisconsin to Cayman Islands

Compare and see reviews for airlines that fly from Wisconsin to Cayman Islands with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Cayman Islands?

Can I find flights from Wisconsin to Cayman Islands with flexible booking policies on momondo?

How can momondo help me find flights from Wisconsin to Cayman Islands?

I’m not ready to book a flight from Wisconsin to Cayman Islands right now. Can momondo alert me if prices change?

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo