What is the cheapest airline that flies from Milwaukee-Mitchell to Caribbean?

American Airlines, Delta, and Southwest are the most popular carriers operating from Milwaukee-Mitchell to Caribbean

What airlines fly to Caribbean?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Caribbean from Milwaukee according to our data. American Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 13 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Caribbean?

Prices for flights from Milwaukee-Mitchell Airport to Caribbean are updated daily.

How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Caribbean?

As of May 2026, there are 7 operators available to choose from for flights from Milwaukee-Mitchell Airport to Caribbean.

How old do you have to be to fly from Milwaukee-Mitchell Airport to Caribbean?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milwaukee-Mitchell Airport to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The travel and health documents required for your trip to Caribbean 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 Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$138 Cheap Flights from Milwaukee to Caribbean in 2026

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Find the cheapest flights from Milwaukee to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:22 pm - 11:50 pm

MKE

SJU

8h 28m

1 stop

3:25 pm - 9:18 pm

SJU

MKE

6h 53m

1 stop

$333American Airlines

Mon, Oct 5 - Fri, Oct 30

8:16 pm - 1:45 pm

MKE

SJU

16h 29m

1 stop

8:35 am - 12:11 am

SJU

MKE

16h 36m

1 stop

$335American Airlines

Mon, Oct 5 - Fri, Oct 30

8:43 am - 2:11 am

MKE

SJU

16h 28m

1 stop

4:05 pm - 7:58 am

SJU

MKE

16h 53m

1 stop

$361Frontier

Thu, Jul 16 - Mon, Jul 20

11:00 am - 11:05 pm

MKE

SJU

11h 05m

1 stop

8:55 pm - 8:55 am

SJU

MKE

13h 00m

1 stop

$365Southwest

Mon, Aug 10 - Thu, Aug 13

12:10 pm - 2:29 pm

MKE

PUJ

25h 19m

1 stop

3:39 pm - 11:13 am

PUJ

MKE

20h 34m

1 stop

$420Frontier

Mon, Aug 17 - Thu, Aug 20

5:45 am - 3:34 pm

MKE

MBJ

9h 49m

1 stop

1:32 pm - 11:24 pm

MBJ

MKE

9h 52m

1 stop

$422Delta

Sun, Oct 18 - Wed, Oct 28

5:55 pm - 11:25 am

MKE

MBJ

17h 30m

1 stop

12:50 pm - 9:22 am

MBJ

MKE

20h 32m

2 stops

$427Delta

Mon, Oct 19 - Tue, Oct 27

7:00 pm - 12:33 pm

MKE

SXM

16h 33m

2 stops

3:50 pm - 7:40 pm

SXM

MKE

28h 50m

2 stops

$608United Airlines

Sat, Jun 6 - Fri, Jun 12

7:00 pm - 3:12 pm

MKE

STI

19h 12m

2 stops

6:00 am - 12:09 am

STI

MKE

19h 09m

2 stops

$613United Airlines

Sat, Oct 3 - Tue, Oct 6

6:25 pm - 12:45 pm

MKE

AUA

17h 20m

2 stops

1:45 pm - 8:45 pm

AUA

MKE

8h 00m

1 stop

$686Southwest

Mon, Aug 24 - Mon, Aug 31

American Airlines flights from Milwaukee to Caribbean

Our best American Airlines deals on Milwaukee to Caribbean flight tickets

American Airlines

Oct 5

MKE2:22 pmMilwaukee-Mitchell

8h 28m

1 stop

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Oct 30

SJU3:25 pmSan Juan Luis Munoz Marin Intl

6h 53m

1 stop

MKE9:18 pmMilwaukee-Mitchell

$333

American Airlines

Oct 5

MKE8:16 pmMilwaukee-Mitchell

16h 29m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

Oct 30

SJU8:35 amSan Juan Luis Munoz Marin Intl

16h 36m

1 stop

MKE12:11 amMilwaukee-Mitchell

$335

American Airlines

Aug 17

MKE6:16 amMilwaukee-Mitchell

15h 08m

1 stop

SJU10:24 pmSan Juan Luis Munoz Marin Intl

Aug 21

SJU6:51 amSan Juan Luis Munoz Marin Intl

17h 32m

1 stop

MKE11:23 pmMilwaukee-Mitchell

$336

United Airlines flights from Milwaukee to Caribbean

Our best United Airlines deals on Milwaukee to Caribbean flight tickets

United Airlines

Oct 5

MKE5:10 amMilwaukee-Mitchell

8h 34m

1 stop

SJU2:44 pmSan Juan Luis Munoz Marin Intl

Oct 30

SJU7:30 amSan Juan Luis Munoz Marin Intl

12h 09m

2 stops

MKE6:39 pmMilwaukee-Mitchell

$379

United Airlines

Oct 10

MKE6:00 amMilwaukee-Mitchell

13h 38m

2 stops

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Oct 15

SJU3:56 pmSan Juan Luis Munoz Marin Intl

7h 28m

1 stop

MKE10:24 pmMilwaukee-Mitchell

$405

United Airlines

Sep 22

MKE10:30 amMilwaukee-Mitchell

9h 08m

1 stop

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Sep 22

SJU1:00 amSan Juan Luis Munoz Marin Intl

10h 00m

2 stops

MKE10:00 amMilwaukee-Mitchell

$411

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 10/5

2:22 pm-11:50 pm

1 stop8h 28m

San Juan Luis Munoz Marin Intl

Fri 10/30

3:25 pm-9:18 pm

1 stop6h 53m

$333

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 10/5

8:16 pm-1:45 pm

1 stop16h 29m

San Juan Luis Munoz Marin Intl

Fri 10/30

8:35 am-12:11 am

1 stop16h 36m

$335

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Thu 7/16

8:43 am-2:11 am

1 stop16h 28m

San Juan Luis Munoz Marin Intl

Mon 7/20

4:05 pm-7:58 am

1 stop16h 53m

$361

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 8/10

11:00 am-11:05 pm

1 stop11h 05m

San Juan Luis Munoz Marin Intl

Thu 8/13

8:55 pm-8:55 am

1 stop13h 00m

$365

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

Mon 8/17

12:10 pm-2:29 pm

1 stop25h 19m

Punta Cana

Thu 8/20

3:39 pm-11:13 am

1 stop20h 34m

$420

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sun 10/18

5:45 am-3:34 pm

1 stop9h 49m

Montego Bay Sangster Intl

Wed 10/28

1:32 pm-11:24 pm

1 stop9h 52m

$422

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 10/19

5:55 pm-11:25 am

1 stop17h 30m

Montego Bay Sangster Intl

Tue 10/27

12:50 pm-9:22 am

2 stops20h 32m

$427

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

Sat 6/6

7:00 pm-12:33 pm

2 stops16h 33m

Simpson Bay Princess Juliana

Fri 6/12

3:50 pm-7:40 pm

2 stops28h 50m

$608

MilwaukeeSantiago de los Caballeros

MKE - STI

MKESTI

Milwaukee-Mitchell

Sat 10/3

7:00 pm-3:12 pm

2 stops19h 12m

Santiago de los Caballeros

Tue 10/6

6:00 am-12:09 am

2 stops19h 09m

$613

MilwaukeeOranjestad

MKE - AUA

MKEAUA

Milwaukee-Mitchell

Mon 8/24

6:25 pm-12:45 pm

2 stops17h 20m

Oranjestad Reina Beatrix

Mon 8/31

1:45 pm-8:45 pm

1 stop8h 00m

$686

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 Milwaukee to Caribbean

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

What is the cheapest month to fly to Caribbean?

In general, October is the cheapest month to fly from Milwaukee to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $108. If you don’t want to visit Caribbean in October, then you should wait until November to fly from Milwaukee, when ticket prices are also cheap, with an average price of $113.

What is the cheapest Milwaukee-Mitchell to Caribbean flight route?

Fly from Milwaukee-Mitchell to Punta Cana for the best Milwaukee-Mitchell - Caribbean flight prices

How far in advance should I book a flight from Milwaukee to Caribbean?

You are more likely to see cheaper flights to Caribbean from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $450 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Milwaukee for as low as $369 on momondo.

Can stopping save me money on Milwaukee to Caribbean flights?

You could potentially save up to 6% on your flight if you consider stops on a Milwaukee to Caribbean flight.

Cheap Milwaukee to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milwaukee to Caribbean

Fastest flight time	5h 40m
Direct flights	None

The fastest flight from Milwaukee to Caribbean takes 5h 40m

There are no direct flights from Milwaukee to Caribbean. There are no popular flight routes from Milwaukee to Caribbean.

Search flight deals

Frequently asked questions about flying from Milwaukee to Caribbean

When did momondo last update prices for flights from Milwaukee-Mitchell Airport to Caribbean?
Prices for flights from Milwaukee-Mitchell Airport to Caribbean are updated daily.
How many operators does momondo search for flights from Milwaukee-Mitchell Airport to Caribbean?
As of May 2026, there are 7 operators available to choose from for flights from Milwaukee-Mitchell Airport to Caribbean.
How old do you have to be to fly from Milwaukee-Mitchell Airport to Caribbean?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milwaukee-Mitchell Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents required for your trip to Caribbean 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 Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Milwaukee to Caribbean?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Milwaukee to Caribbean is Boeing 737-800 (60.87% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (13.04%), Airbus A321neo (8.70%), and Boeing 737 (8.70%).

Best airlines flying from Milwaukee to Caribbean

Compare and see reviews for airlines that fly from Milwaukee to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $112	Free Cancellation	Rating 7.9 8,453 reviews	Search Delta flights
Frontier	PriceFrom $156	Free Cancellation	Rating 5.6 2,951 reviews	Search Frontier flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 9,718 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $219	Free Cancellation	Rating 6.2 8,625 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,663 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,299 reviews	Search Southwest flights
Sun Country Air	PriceFrom $547	Free Cancellation	Rating 6.8 334 reviews	Search Sun Country Air flights

Why use momondo?

Why should I use momondo to find a flight deal from Milwaukee to Caribbean?

It is quick and easy to find Milwaukee to Caribbean flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean that suits you.

Can I find flights from Milwaukee to Caribbean with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean from Milwaukee with this policy.

How can momondo help me find flights from Milwaukee to Caribbean?

Once you have performed a search for Milwaukee to Caribbean 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 Milwaukee to Caribbean right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Milwaukee to Caribbean now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean and let you know when they change.