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

The number of flights available between Wisconsin and Cayman Islands is 8 per week as of April 2026. The most frequent departure day is Sat, with 25% of weekly flights leaving on this day.

What airlines fly to Cayman Islands?

American Airlines, United Airlines and Delta 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.

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 46m on average. On the other hand, flying from Madison to George Town takes 6h 11m 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?

Air Canada and Delta 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 April 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.

$128 Cheap Flights from Wisconsin to the Cayman Islands in 2026

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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.

1:55 pm - 11:25 am

ORD

GCM

21h 30m

2 stops

10:55 am - 9:00 am

GCM

ORD

22h 05m

1 stop

$350Air Canada

Wed, Jun 10 - Sat, Jun 13

6:22 pm - 11:25 am

ORD

GCM

41h 03m

2 stops

10:55 am - 9:00 am

GCM

ORD

22h 05m

1 stop

$355Air Canada

Sat, Jun 6 - Sat, Jun 13

8:55 pm - 12:30 pm

MSN

GCM

15h 35m

2 stops

1:35 pm - 8:56 am

GCM

MSN

19h 21m

2 stops

$466United Airlines

Thu, May 7 - Thu, May 14

7:37 pm - 1:10 pm

MKE

GCM

17h 33m

2 stops

1:20 pm - 8:58 am

GCM

MKE

19h 38m

2 stops

$501American Airlines

Sat, Sep 5 - Sat, Sep 12

4:24 pm - 11:25 am

MKE

GCM

19h 01m

1 stop

12:35 pm - 12:10 am

GCM

MKE

11h 35m

1 stop

$505American Airlines

Sat, Sep 5 - Sat, Sep 12

5:23 am - 11:54 am

MKE

GCM

6h 31m

1 stop

1:19 pm - 9:02 pm

GCM

MKE

7h 43m

1 stop

$520Delta

Fri, May 8 - Tue, May 12

5:55 am - 11:41 am

MKE

GCM

5h 46m

1 stop

12:55 pm - 9:59 pm

GCM

MKE

9h 04m

1 stop

$531Delta

Sat, Sep 5 - Sat, Sep 12

7:10 pm - 12:10 pm

MSP

GCM

17h 00m

2 stops

1:05 pm - 10:35 pm

GCM

MSP

9h 30m

2 stops

$535Southwest

Sun, May 3 - Sat, May 9

8:15 am - 12:30 pm

MKE

GCM

28h 15m

1 stop

1:35 pm - 10:45 pm

GCM

MKE

9h 10m

1 stop

$551United Airlines

Mon, May 18 - Fri, May 22

6:10 pm - 12:10 pm

MSP

GCM

18h 00m

2 stops

1:05 pm - 11:00 pm

GCM

MSP

9h 55m

2 stops

$570Southwest

Mon, May 18 - Thu, May 21

American Airlines flights from Wisconsin to Cayman Islands

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

American Airlines

Sep 5

MKE7:37 pmMilwaukee-Mitchell

17h 33m

2 stops

GCM1:10 pmGeorge Town Owen Roberts Intl

Sep 12

GCM1:20 pmGeorge Town Owen Roberts Intl

19h 38m

2 stops

MKE8:58 amMilwaukee-Mitchell

$501

American Airlines

Sep 5

MKE4:24 pmMilwaukee-Mitchell

19h 01m

1 stop

GCM11:25 amGeorge Town Owen Roberts Intl

Sep 12

GCM12:35 pmGeorge Town Owen Roberts Intl

11h 35m

1 stop

MKE12:10 amMilwaukee-Mitchell

$505

American Airlines

Sep 5

MKE2:36 pmMilwaukee-Mitchell

20h 49m

1 stop

GCM11:25 amGeorge Town Owen Roberts Intl

Sep 12

GCM1:20 pmGeorge Town Owen Roberts Intl

19h 38m

2 stops

MKE8:58 amMilwaukee-Mitchell

$510

Air Canada flights from Wisconsin to Cayman Islands

Our best Air Canada deals on Wisconsin to Cayman Islands flight tickets

Air Canada

Jun 10

ORD1:55 pmChicago O'Hare Intl

21h 30m

2 stops

GCM11:25 amGeorge Town Owen Roberts Intl

Jun 13

GCM10:55 amGeorge Town Owen Roberts Intl

22h 05m

1 stop

ORD9:00 amChicago O'Hare Intl

$350

Air Canada

Jun 6

ORD6:22 pmChicago O'Hare Intl

41h 03m

2 stops

GCM11:25 amGeorge Town Owen Roberts Intl

Jun 13

GCM10:55 amGeorge Town Owen Roberts Intl

22h 05m

1 stop

ORD9:00 amChicago O'Hare Intl

$355

Air Canada

Jun 5

ORD8:20 pmChicago O'Hare Intl

13h 40m

1 stop

GCM10:00 amGeorge Town Owen Roberts Intl

Jun 8

GCM12:25 pmGeorge Town Owen Roberts Intl

25h 00m

1 stop

ORD1:25 pmChicago O'Hare Intl

$365

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

Cheapest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 6/10

1:55 pm-11:25 am

2 stops21h 30m

George Town Owen Roberts Intl

Sat 6/13

10:55 am-9:00 am

1 stop22h 05m

$350

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 6/6

6:22 pm-11:25 am

2 stops41h 03m

George Town Owen Roberts Intl

Sat 6/13

10:55 am-9:00 am

1 stop22h 05m

$355

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Thu 5/7

8:55 pm-12:30 pm

2 stops15h 35m

George Town Owen Roberts Intl

Thu 5/14

1:35 pm-8:56 am

2 stops19h 21m

$466

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 9/5

7:37 pm-1:10 pm

2 stops17h 33m

George Town Owen Roberts Intl

Sat 9/12

1:20 pm-8:58 am

2 stops19h 38m

$501

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 9/5

4:24 pm-11:25 am

1 stop19h 01m

George Town Owen Roberts Intl

Sat 9/12

12:35 pm-12:10 am

1 stop11h 35m

$505

Quickest round-trip

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Fri 5/8

5:23 am-11:54 am

1 stop6h 31m

George Town Owen Roberts Intl

Tue 5/12

1:19 pm-9:02 pm

1 stop7h 43m

$520

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Sat 9/5

5:55 am-11:41 am

1 stop5h 46m

George Town Owen Roberts Intl

Sat 9/12

12:55 pm-9:59 pm

1 stop9h 04m

$531

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Sun 5/3

7:10 pm-12:10 pm

2 stops17h 00m

George Town Owen Roberts Intl

Sat 5/9

1:05 pm-10:35 pm

2 stops9h 30m

$535

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Mon 5/18

8:15 am-12:30 pm

1 stop28h 15m

George Town Owen Roberts Intl

Fri 5/22

1:35 pm-10:45 pm

1 stop9h 10m

$551

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Mon 5/18

6:10 pm-12:10 pm

2 stops18h 00m

George Town Owen Roberts Intl

Thu 5/21

1:05 pm-11:00 pm

2 stops9h 55m

$570

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 September is also cheap. Prices for this month can be found on momondo for an average of $531.

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	Mon, Thu, Fri, Sat and Sun
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 on Monday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.

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

Search flight deals

Frequently asked questions about flying from Wisconsin to the 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 April 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
United Airlines	PriceFrom $383	Free Cancellation	Rating 7.4 9,569 reviews	Search United Airlines flights
Delta	PriceFrom $406	Free Cancellation	Rating 7.9 8,406 reviews	Search Delta flights
American Airlines	PriceFrom $484	Free Cancellation	Rating 7.1 11,572 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.

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Popular cities in the Cayman Islands

Flights to George Townfrom $269

Flights to Cayman Bracfrom $344

Flights to Little Caymanfrom $399

Cheap flights from Wisconsin to the Cayman Islands from $128

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 6/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Filter for what you want

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American Airlines flights from Wisconsin to Cayman Islands

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

Air Canada flights from Wisconsin to Cayman Islands

Our best Air Canada deals on Wisconsin to Cayman Islands flight tickets

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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

Frequently asked questions about flying from Wisconsin to the 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?

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

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