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Cheap flights from Wisconsin to the Cayman Islands from $127

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 1/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Wisconsin to the Cayman Islands

Cheap round-trip flights

Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 11:42 pmGCM-ORD
12h 47m1 stop
$357Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Spirit Airlines Logo
5:59 pm - 11:00 amORD-GCM
16h 01m1 stop
Spirit Airlines Logo
11:55 am - 11:42 pmGCM-ORD
12h 47m1 stop
$377Spirit Airlines
Find Deal
Sat, Jan 24 - Sat, Jan 31
Delta Logo
5:45 am - 12:35 pmMKE-GCM
5h 50m1 stop
Delta Logo
2:00 pm - 11:27 pmGCM-MKE
10h 27m1 stop
$396Delta
Find Deal
Tue, Jan 20 - Fri, Jan 30
Air Canada Logo
3:35 pm - 11:20 amORD-GCM
19h 45m2 stops
Air Canada Logo
1:30 pm - 9:13 amGCM-ORD
20h 43m1 stop
$449Air Canada
Find Deal
Thu, Oct 30 - Sun, Nov 2
Air Canada Logo
8:25 pm - 11:55 amORD-GCM
15h 30m1 stop
Air Canada Logo
12:50 pm - 1:14 pmGCM-ORD
24h 24m1 stop
$462Air Canada
Find Deal
Sun, Oct 12 - Mon, Oct 20
Delta Logo
5:45 am - 12:35 pmMKE-GCM
5h 50m1 stop
Delta Logo
2:00 pm - 11:27 pmGCM-MKE
10h 27m1 stop
$467Delta
Find Deal
Thu, Jan 22 - Fri, Jan 30
Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
Logo
4:45 pm - 9:22 amGCM-ORD
16h 37m1 stop
$467
Find Deal
Thu, Oct 2 - Thu, Oct 9
Logo
10:27 am - 9:20 pmORD-GCM
10h 53m1 stop
Logo
4:45 pm - 9:18 amGCM-ORD
16h 33m1 stop
$474
Find Deal
Fri, Sep 19 - Sun, Sep 21
Southwest Logo
6:15 pm - 12:55 pmMSP-GCM
17h 40m2 stops
Southwest Logo
1:50 pm - 9:50 pmGCM-MSP
9h 00m2 stops
$481Southwest
Find Deal
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
6:05 am - 12:55 pmORD-GCM
5h 50m1 stop
Southwest Logo
1:50 pm - 9:50 pmGCM-ORD
9h 00m1 stop
$485Southwest
Find Deal
Fri, Feb 6 - Fri, Feb 13

Spirit Airlines flights from Wisconsin to Cayman Islands

Our best Spirit Airlines deals on Wisconsin to Cayman Islands flight tickets
Spirit Airlines
Jan 24
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Jan 31
GCM11:55 amGeorge Town Owen Roberts Intl
12h 47m
1 stop
ORD11:42 pmChicago O'Hare Intl
$357
Find similar
Spirit Airlines
Jan 24
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Jan 31
GCM11:55 amGeorge Town Owen Roberts Intl
12h 47m
1 stop
ORD11:42 pmChicago O'Hare Intl
$377
Find similar
Spirit Airlines
Jan 24
ORD5:59 pmChicago O'Hare Intl
16h 01m
1 stop
GCM11:00 amGeorge Town Owen Roberts Intl
Jan 31
GCM11:55 amGeorge Town Owen Roberts Intl
10h 05m
1 stop
ORD9:00 pmChicago O'Hare Intl
$379
Find similar

Sun Country Air flights from Wisconsin to Cayman Islands

Our best Sun Country Air deals on Wisconsin to Cayman Islands flight tickets
Sun Country Air
Jan 10
MSP1:24 pmMinneapolis St Paul
4h 15m
GCM6:39 pmGeorge Town Owen Roberts Intl
Jan 17
GCM7:40 pmGeorge Town Owen Roberts Intl
4h 38m
MSP11:18 pmMinneapolis St Paul
$497
Find similar
Sun Country Air
Dec 20
MSP1:36 pmMinneapolis St Paul
4h 20m
GCM6:56 pmGeorge Town Owen Roberts Intl
Dec 27
GCM8:00 pmGeorge Town Owen Roberts Intl
4h 45m
MSP11:45 pmMinneapolis St Paul
$506
Find similar
Sun Country Air
Feb 14
MSP1:24 pmMinneapolis St Paul
4h 15m
GCM6:39 pmGeorge Town Owen Roberts Intl
Feb 21
GCM7:41 pmGeorge Town Owen Roberts Intl
4h 43m
MSP11:24 pmMinneapolis St Paul
$516
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 20, 2025.
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

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 1/31

11:55 am-11:42 pm

1 stop12h 47m

$357

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/24

5:59 pm-11:00 am

1 stop16h 01m

George Town Owen Roberts Intl

Sat 1/31

11:55 am-11:42 pm

1 stop12h 47m

$377

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Tue 1/20

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Fri 1/30

2:00 pm-11:27 pm

1 stop10h 27m

$396

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 10/30

3:35 pm-11:20 am

2 stops19h 45m

George Town Owen Roberts Intl

Sun 11/2

1:30 pm-9:13 am

1 stop20h 43m

$449

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 10/12

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

Mon 10/20

12:50 pm-1:14 pm

1 stop24h 24m

$462

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

Thu 1/22

5:45 am-12:35 pm

1 stop5h 50m

George Town Owen Roberts Intl

Fri 1/30

2:00 pm-11:27 pm

1 stop10h 27m

$467

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 10/2

10:27 am-9:20 pm

1 stop10h 53m

George Town Owen Roberts Intl

Thu 10/9

4:45 pm-9:22 am

1 stop16h 37m

$467

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 9/19

10:27 am-9:20 pm

1 stop10h 53m

George Town Owen Roberts Intl

Sun 9/21

4:45 pm-9:18 am

1 stop16h 33m

$474

MinneapolisGeorge Town

MSP - GCM

MSPGCM

Minneapolis St Paul

Wed 1/14

6:15 pm-12:55 pm

2 stops17h 40m

George Town Owen Roberts Intl

Wed 1/21

1:50 pm-9:50 pm

2 stops9h 00m

$481

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 2/6

6:05 am-12:55 pm

1 stop5h 50m

George Town Owen Roberts Intl

Fri 2/13

1:50 pm-9:50 pm

1 stop9h 00m

$485

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

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.

How far in advance should I book a flight to Cayman Islands?

You are more likely to see cheaper flights to Cayman Islands from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $612 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Wisconsin for as low as $529 on momondo.

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

You could potentially save up to 17% 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

Mon, Tue, Thu, Fri, Sat and Sun

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 on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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?

  • 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 AirlinesPriceFrom $273Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
DeltaPriceFrom $310Free CancellationRating
7.9
7,982 reviews
Search Delta flights
American AirlinesPriceFrom $497Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $526Free CancellationRating
8.0
4,246 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.

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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
Flights to George Townfrom $267
Flights to Cayman Bracfrom $335
Flights to Little Caymanfrom $468