How many flights depart from Wisconsin to Cayman Islands on average per week?

The number of flights available between Wisconsin and Cayman Islands is 11 per week as of February 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.

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 59% 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.

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

Southwest, American Airlines, 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 51m on average. On the other hand, flying from Milwaukee to George Town takes 5h 55m 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.

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 February 2026, 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.

$75 Cheap Flights from Wisconsin to the Cayman Islands in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

6:40 pm - 10:10 am

ORD

GCM

15h 30m

1 stop

11:30 am - 6:54 pm

GCM

ORD

31h 24m

3 stops

$458Multiple Airlines

Thu, Apr 9 - Wed, Apr 15

8:00 am - 10:25 am

ORD

GCM

26h 25m

1 stop

5:05 pm - 8:25 am

GCM

ORD

15h 20m

1 stop

$459Multiple Airlines

Sun, Mar 15 - Sun, Mar 22

6:22 pm - 11:30 am

ORD

GCM

41h 08m

2 stops

2:05 pm - 10:17 am

GCM

ORD

20h 12m

2 stops

$460Multiple Airlines

Tue, May 26 - Tue, Jun 2

3:45 pm - 10:10 am

ORD

GCM

18h 25m

2 stops

11:55 am - 7:58 am

GCM

ORD

20h 03m

2 stops

$464Air Canada

Thu, Apr 9 - Thu, Apr 16

6:40 pm - 10:10 am

ORD

GCM

15h 30m

1 stop

11:55 am - 7:58 am

GCM

ORD

20h 03m

2 stops

$465Air Canada

Thu, Apr 9 - Thu, Apr 16

9:18 am - 12:43 pm

ORD

GCM

26h 25m

3 stops

1:15 pm - 7:51 pm

GCM

ORD

6h 36m

1 stop

$468Spirit Airlines

Sat, Mar 7 - Sat, Mar 14

6:10 pm - 12:10 pm

MSP

GCM

18h 00m

2 stops

1:05 pm - 9:40 am

GCM

MSP

20h 35m

2 stops

$507Southwest

Thu, Apr 9 - Thu, Apr 16

8:24 pm - 11:00 am

MSN

GCM

14h 36m

2 stops

12:35 pm - 11:01 pm

GCM

MSN

10h 26m

1 stop

$526American Airlines

Thu, Apr 9 - Tue, Apr 14

5:08 pm - 11:33 am

MSN

GCM

18h 25m

1 stop

12:35 pm - 11:01 pm

GCM

MSN

10h 26m

1 stop

$532American Airlines

Thu, Apr 9 - Tue, Apr 14

2:40 pm - 12:10 pm

MKE

GCM

21h 30m

2 stops

12:50 pm - 11:10 pm

GCM

MKE

10h 20m

2 stops

$578Southwest

Wed, May 13 - Sun, May 17

Spirit Airlines flights from Wisconsin to Cayman Islands

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

Spirit Airlines

Feb 25

ORD8:16 pmChicago O'Hare Intl

16h 27m

1 stop

GCM1:43 pmGeorge Town Owen Roberts Intl

Mar 1

GCM2:49 pmGeorge Town Owen Roberts Intl

9h 58m

1 stop

ORD11:47 pmChicago O'Hare Intl

$458

Spirit Airlines

Mar 7

ORD9:18 amChicago O'Hare Intl

26h 25m

3 stops

GCM12:43 pmGeorge Town Owen Roberts Intl

Mar 14

GCM1:15 pmGeorge Town Owen Roberts Intl

6h 36m

1 stop

ORD7:51 pmChicago O'Hare Intl

$468

Spirit Airlines

Mar 15

ORD5:05 amChicago O'Hare Intl

7h 52m

1 stop

GCM12:57 pmGeorge Town Owen Roberts Intl

Mar 19

GCM1:52 pmGeorge Town Owen Roberts Intl

34h 30m

3 stops

ORD12:22 amChicago O'Hare Intl

$481

Delta flights from Wisconsin to Cayman Islands

Our best Delta deals on Wisconsin to Cayman Islands flight tickets

Delta

Apr 6

ORD7:59 pmChicago O'Hare Intl

15h 48m

1 stop

GCM11:47 amGeorge Town Owen Roberts Intl

Apr 15

GCM1:25 pmGeorge Town Owen Roberts Intl

10h 34m

1 stop

ORD11:59 pmChicago O'Hare Intl

$499

Delta

Apr 6

ORD5:40 pmChicago O'Hare Intl

18h 07m

2 stops

GCM11:47 amGeorge Town Owen Roberts Intl

Apr 14

GCM1:25 pmGeorge Town Owen Roberts Intl

20h 54m

2 stops

ORD10:19 amChicago O'Hare Intl

$504

Delta

May 18

MSN6:19 pmMadison Truax Field

17h 35m

2 stops

GCM11:54 amGeorge Town Owen Roberts Intl

May 28

GCM1:19 pmGeorge Town Owen Roberts Intl

19h 30m

2 stops

MSN8:49 amMadison Truax Field

$564

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 4/9

6:40 pm-10:10 am

1 stop15h 30m

George Town Owen Roberts Intl

Wed 4/15

11:30 am-6:54 pm

3 stops31h 24m

$458

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/15

8:00 am-10:25 am

1 stop26h 25m

George Town Owen Roberts Intl

Sun 3/22

5:05 pm-8:25 am

1 stop15h 20m

$459

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/26

6:22 pm-11:30 am

2 stops41h 08m

George Town Owen Roberts Intl

Tue 6/2

2:05 pm-10:17 am

2 stops20h 12m

$460

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/9

3:45 pm-10:10 am

2 stops18h 25m

George Town Owen Roberts Intl

Thu 4/16

11:55 am-7:58 am

2 stops20h 03m

$464

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/9

6:40 pm-10:10 am

1 stop15h 30m

George Town Owen Roberts Intl

Thu 4/16

11:55 am-7:58 am

2 stops20h 03m

$465

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 3/7

9:18 am-12:43 pm

3 stops26h 25m

George Town Owen Roberts Intl

Sat 3/14

1:15 pm-7:51 pm

1 stop6h 36m

$468

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Thu 4/9

6:10 pm-12:10 pm

2 stops18h 00m

George Town Owen Roberts Intl

Thu 4/16

1:05 pm-9:40 am

2 stops20h 35m

$507

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 4/9

8:24 pm-11:00 am

2 stops14h 36m

George Town Owen Roberts Intl

Tue 4/14

12:35 pm-11:01 pm

1 stop10h 26m

$526

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 4/9

5:08 pm-11:33 am

1 stop18h 25m

George Town Owen Roberts Intl

Tue 4/14

12:35 pm-11:01 pm

1 stop10h 26m

$532

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Wed 5/13

2:40 pm-12:10 pm

2 stops21h 30m

George Town Owen Roberts Intl

Sun 5/17

12:50 pm-11:10 pm

2 stops10h 20m

$578

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.

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 February 2026, 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 $359	Free Cancellation	Rating 7.9 8,239 reviews	Search Delta flights
United Airlines	PriceFrom $383	Free Cancellation	Rating 7.4 9,344 reviews	Search United Airlines flights
American Airlines	PriceFrom $435	Free Cancellation	Rating 7.2 11,344 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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Thu 3/26

Thu 4/2

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the Cayman Islands

Popular cities

Other flights from Wisconsin

Other flights to the Cayman Islands

Airlines

Cabin classes

Complete your trip

Feeling lucky

Popular cities in the Cayman Islands

Flights to George Townfrom $223

Flights to Cayman Bracfrom $335

Flights to Little Caymanfrom $342

Cheap flights from Wisconsin to the Cayman Islands from $75

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 4/4. 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

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

What is the cheapest month to fly to Cayman Islands?

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

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

What airlines fly to Cayman Islands?

How many flights depart from Wisconsin to Cayman Islands on average per week?

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

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

Wisconsin flight routes

According to popular flight searches on momondo this year

Cayman Islands flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to the Cayman Islands

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to the Cayman Islands

List of cabin classes available on flights landing in the Cayman Islands. Availability may vary depending on flight origin and airline.

Complete your trip to the Cayman Islands

Explore popular destinations other users love

According to popular flight searches on momondo this year