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

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

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 Madison to George Town takes 5h 39m on average. On the other hand, flying from Milwaukee to George Town takes 5h 50m 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 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 60% of people opting to fly with this airline when traveling to Cayman Islands. Keep in mind that there are 4 different airlines that fly to Cayman Islands on a routine basis, so you have a few additional options to choose from.

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 October 2025, there are 5 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.

$113 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

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One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

5:05 am - 1:40 pmORD-GCM

7h 35m1 stop

2:35 pm - 11:42 pmGCM-ORD

10h 07m1 stop

$305Spirit Airlines

Find Deal

Thu, Jan 22 - Thu, Jan 29

7:00 am - 4:55 pmORD-GCM

8h 55m1 stop

5:56 pm - 12:19 amGCM-ORD

7h 23m1 stop

$306Spirit Airlines

Find Deal

Sat, Dec 6 - Sat, Dec 13

8:45 am - 1:45 pmORD-GCM

4h 00mnonstop

2:50 pm - 6:04 pmGCM-ORD

4h 14mnonstop

$338United Airlines

Find Deal

Wed, Dec 24 - Wed, Dec 31

5:00 am - 12:05 pmORD-GCM

6h 05m1 stop

3:50 pm - 7:00 pmGCM-ORD

4h 10mnonstop

$342American Airlines

Find Deal

Wed, Nov 19 - Sat, Nov 22

9:50 am - 2:49 pmORD-GCM

3h 59mnonstop

1:01 pm - 8:26 pmGCM-ORD

8h 25m1 stop

$343American Airlines

Find Deal

Sat, Nov 29 - Sat, Dec 6

8:45 am - 1:45 pmORD-GCM

4h 00mnonstop

2:25 pm - 11:33 pmGCM-ORD

10h 08m1 stop

$348United Airlines

Find Deal

Sat, Dec 6 - Sat, Dec 13

5:20 am - 12:44 pmORD-GCM

6h 24m1 stop

1:50 pm - 9:56 pmGCM-ORD

9h 06m1 stop

$354Delta

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Thu, Nov 6 - Mon, Nov 10

5:50 am - 12:35 pmORD-GCM

5h 45m1 stop

2:00 pm - 11:54 pmGCM-ORD

10h 54m1 stop

$356Delta

Find Deal

Wed, Jan 21 - Tue, Jan 27

4:22 pm - 4:05 pmORD-GCM

22h 43m2 stops

5:56 pm - 12:19 amGCM-ORD

7h 23m1 stop

$412Multiple Airlines

Find Deal

Tue, Dec 2 - Sat, Dec 6

11:40 am - 9:15 pmORD-GCM

8h 35m1 stop

5:56 pm - 12:19 amGCM-ORD

7h 23m1 stop

$414Multiple Airlines

Find Deal

Mon, Dec 1 - Sat, Dec 6

Southwest flights from Wisconsin to Cayman Islands

Our best Southwest deals on Wisconsin to Cayman Islands flight tickets

Southwest

Dec 31

ORD6:05 amChicago O'Hare Intl

5h 30m

1 stop

GCM12:35 pmGeorge Town Owen Roberts Intl

Jan 7

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 00m

1 stop

ORD9:50 pmChicago O'Hare Intl

$413

Find similar

Southwest

Jan 9

MKE4:50 pmMilwaukee-Mitchell

18h 40m

2 stops

GCM12:30 pmGeorge Town Owen Roberts Intl

Jan 16

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 45m

2 stops

MKE10:35 pmMilwaukee-Mitchell

$483

Find similar

Southwest

Feb 8

MSP6:15 pmMinneapolis St Paul

17h 40m

2 stops

GCM12:55 pmGeorge Town Owen Roberts Intl

Feb 13

GCM1:50 pmGeorge Town Owen Roberts Intl

10h 50m

2 stops

MSP11:40 pmMinneapolis St Paul

$489

Find similar

Delta flights from Wisconsin to Cayman Islands

Our best Delta deals on Wisconsin to Cayman Islands flight tickets

Delta

Nov 6

ORD5:20 amChicago O'Hare Intl

6h 24m

1 stop

GCM12:44 pmGeorge Town Owen Roberts Intl

Nov 10

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 06m

1 stop

ORD9:56 pmChicago O'Hare Intl

$354

Find similar

Delta

Jan 21

ORD5:50 amChicago O'Hare Intl

5h 45m

1 stop

GCM12:35 pmGeorge Town Owen Roberts Intl

Jan 27

GCM2:00 pmGeorge Town Owen Roberts Intl

10h 54m

1 stop

ORD11:54 pmChicago O'Hare Intl

$356

Find similar

Delta

Nov 26

ORD5:08 pmChicago O'Hare Intl

18h 27m

2 stops

GCM12:35 pmGeorge Town Owen Roberts Intl

Dec 4

GCM1:50 pmGeorge Town Owen Roberts Intl

11h 11m

1 stop

ORD12:01 amChicago O'Hare Intl

$357

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

Thu 1/22

5:05 am-1:40 pm

1 stop7h 35m

George Town Owen Roberts Intl

Thu 1/29

2:35 pm-11:42 pm

1 stop10h 07m

$305

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

7:00 am-4:55 pm

1 stop8h 55m

George Town Owen Roberts Intl

Sat 12/13

5:56 pm-12:19 am

1 stop7h 23m

$306

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Wed 12/31

2:50 pm-6:04 pm

Nonstop4h 14m

$338

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 11/19

5:00 am-12:05 pm

1 stop6h 05m

George Town Owen Roberts Intl

Sat 11/22

3:50 pm-7:00 pm

Nonstop4h 10m

$342

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 11/29

9:50 am-2:49 pm

Nonstop3h 59m

George Town Owen Roberts Intl

Sat 12/6

1:01 pm-8:26 pm

1 stop8h 25m

$343

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 12/6

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Sat 12/13

2:25 pm-11:33 pm

1 stop10h 08m

$348

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 11/6

5:20 am-12:44 pm

1 stop6h 24m

George Town Owen Roberts Intl

Mon 11/10

1:50 pm-9:56 pm

1 stop9h 06m

$354

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/21

5:50 am-12:35 pm

1 stop5h 45m

George Town Owen Roberts Intl

Tue 1/27

2:00 pm-11:54 pm

1 stop10h 54m

$356

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 12/2

4:22 pm-4:05 pm

2 stops22h 43m

George Town Owen Roberts Intl

Sat 12/6

5:56 pm-12:19 am

1 stop7h 23m

$412

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 12/1

11:40 am-9:15 pm

1 stop8h 35m

George Town Owen Roberts Intl

Sat 12/6

5:56 pm-12:19 am

1 stop7h 23m

$414

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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 20% 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	3h 46m
Direct flights	Every day
Airports in Cayman Islands	1 airport

The fastest flight from Wisconsin to Cayman Islands takes 3h 46m

Direct flights go from Wisconsin to Cayman Islands every day.

There is 1 airport near Cayman Islands: 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 October 2025, there are 5 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 7,982 reviews	Search Delta flights
United Airlines	PriceFrom $273	Free Cancellation	Rating 7.4 8,995 reviews	Search United Airlines flights
American Airlines	PriceFrom $513	Free Cancellation	Rating 7.2 11,032 reviews	Search American Airlines flights
Southwest	PriceFrom $526	Free Cancellation	Rating 8.0 4,236 reviews	Search Southwest 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 $205

Flights to Cayman Bracfrom $333

Flights to Little Caymanfrom $403

Cheap flights from Wisconsin to the Cayman Islands from $113

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 1/22. 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

Southwest flights from Wisconsin to Cayman Islands

Our best Southwest deals on Wisconsin to Cayman Islands flight tickets

Delta flights from Wisconsin to Cayman Islands

Our best Delta 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

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

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 20% 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, Southwest, 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