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 38% 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.

How many flights depart from Milwaukee to Caribbean on average per week?

As of March 2026, there are 5 flights per week flying from Milwaukee to Caribbean. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.

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

United Airlines, American Airlines, and Delta are the most popular carriers operating from Milwaukee-Mitchell 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 March 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.

$88 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

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:23 pm - 2:24 pm

MKE

PUJ

19h 01m

1 stop

3:35 pm - 11:14 am

PUJ

MKE

20h 39m

1 stop

$273Frontier

lun., may. 4 - mar., may. 12

5:59 pm - 1:29 pm

MKE

SJU

18h 30m

1 stop

3:16 am - 12:52 pm

SJU

MKE

10h 36m

1 stop

$288Frontier

lun., abr. 6 - vie., abr. 10

7:01 am - 8:51 pm

MKE

SJU

12h 50m

2 stops

6:00 am - 9:41 pm

SJU

MKE

16h 41m

1 stop

$309American Airlines

mar., abr. 28 - mar., may. 5

6:00 am - 1:50 pm

MKE

SJU

6h 50m

1 stop

6:00 am - 9:41 pm

SJU

MKE

16h 41m

1 stop

$314American Airlines

mié., abr. 22 - sáb., may. 2

6:50 am - 3:31 pm

MKE

STT

7h 41m

1 stop

2:10 pm - 8:48 pm

STT

MKE

7h 38m

1 stop

$324United Airlines

mar., abr. 14 - mié., abr. 22

5:56 pm - 1:30 pm

MKE

MBJ

19h 34m

2 stops

2:40 pm - 10:59 pm

MBJ

MKE

8h 19m

1 stop

$352United Airlines

mar., may. 5 - mar., may. 12

1:55 pm - 11:27 am

MKE

MBJ

21h 32m

2 stops

4:32 pm - 9:05 am

MBJ

MKE

16h 33m

1 stop

$367Delta

sáb., abr. 25 - jue., abr. 30

5:23 am - 11:54 am

MKE

GCM

6h 31m

1 stop

1:19 pm - 11:53 pm

GCM

MKE

10h 34m

1 stop

$370Delta

lun., may. 11 - lun., may. 18

5:30 am - 1:30 pm

MKE

SXM

7h 00m

1 stop

2:25 pm - 10:50 pm

SXM

MKE

9h 25m

1 stop

$463Southwest

lun., may. 4 - mié., may. 13

5:40 am - 1:30 pm

MKE

SXM

6h 50m

1 stop

2:25 pm - 10:50 pm

SXM

MKE

9h 25m

1 stop

$498Southwest

mié., abr. 22 - mié., abr. 29

Frontier flights from Milwaukee to Caribbean

Our best Frontier deals on Milwaukee to Caribbean flight tickets

Frontier

May 4

MKE6:23 pmMilwaukee-Mitchell

19h 01m

1 stop

PUJ2:24 pmPunta Cana

May 12

PUJ3:35 pmPunta Cana

20h 39m

1 stop

MKE11:14 amMilwaukee-Mitchell

$273

Frontier

Mar 29

MKE9:01 pmMilwaukee-Mitchell

27h 57m

1 stop

SJU1:58 amSan Juan Luis Munoz Marin Intl

Apr 15

SJU6:30 amSan Juan Luis Munoz Marin Intl

29h 56m

1 stop

MKE11:26 amMilwaukee-Mitchell

$285

Frontier

Mar 31

MKE5:44 pmMilwaukee-Mitchell

7h 19m

1 stop

SJU2:03 amSan Juan Luis Munoz Marin Intl

Apr 3

SJU6:00 amSan Juan Luis Munoz Marin Intl

10h 41m

1 stop

MKE3:41 pmMilwaukee-Mitchell

$288

American Airlines flights from Milwaukee to Caribbean

Our best American Airlines deals on Milwaukee to Caribbean flight tickets

American Airlines

Apr 28

MKE7:01 amMilwaukee-Mitchell

12h 50m

2 stops

SJU8:51 pmSan Juan Luis Munoz Marin Intl

May 5

SJU6:00 amSan Juan Luis Munoz Marin Intl

16h 41m

1 stop

MKE9:41 pmMilwaukee-Mitchell

$309

American Airlines

Apr 22

MKE6:00 amMilwaukee-Mitchell

6h 50m

1 stop

SJU1:50 pmSan Juan Luis Munoz Marin Intl

May 2

SJU6:00 amSan Juan Luis Munoz Marin Intl

16h 41m

1 stop

MKE9:41 pmMilwaukee-Mitchell

$314

American Airlines

Apr 22

MKE7:00 amMilwaukee-Mitchell

6h 49m

1 stop

STT2:49 pmSaint Thomas Island Cyril E King

Apr 28

STT5:05 pmSaint Thomas Island Cyril E King

19h 25m

2 stops

MKE11:30 amMilwaukee-Mitchell

$329

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeePunta Cana

MKE - PUJ

MKEPUJ

Milwaukee-Mitchell

lun. 5/4

6:23 pm-2:24 pm

1 stop19h 01m

Punta Cana

mar. 5/12

3:35 pm-11:14 am

1 stop20h 39m

$273

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

lun. 4/6

5:59 pm-1:29 pm

1 stop18h 30m

San Juan Luis Munoz Marin Intl

vie. 4/10

3:16 am-12:52 pm

1 stop10h 36m

$288

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mar. 4/28

7:01 am-8:51 pm

2 stops12h 50m

San Juan Luis Munoz Marin Intl

mar. 5/5

6:00 am-9:41 pm

1 stop16h 41m

$309

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

mié. 4/22

6:00 am-1:50 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

sáb. 5/2

6:00 am-9:41 pm

1 stop16h 41m

$314

Quickest round-trip

MilwaukeeSaint Thomas Island

MKE - STT

MKESTT

Milwaukee-Mitchell

mar. 4/14

6:50 am-3:31 pm

1 stop7h 41m

Saint Thomas Island Cyril E King

mié. 4/22

2:10 pm-8:48 pm

1 stop7h 38m

$324

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

mar. 5/5

5:56 pm-1:30 pm

2 stops19h 34m

Montego Bay Sangster Intl

mar. 5/12

2:40 pm-10:59 pm

1 stop8h 19m

$352

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

sáb. 4/25

1:55 pm-11:27 am

2 stops21h 32m

Montego Bay Sangster Intl

jue. 4/30

4:32 pm-9:05 am

1 stop16h 33m

$367

MilwaukeeGeorge Town

MKE - GCM

MKEGCM

Milwaukee-Mitchell

lun. 5/11

5:23 am-11:54 am

1 stop6h 31m

George Town Owen Roberts Intl

lun. 5/18

1:19 pm-11:53 pm

1 stop10h 34m

$370

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

lun. 5/4

5:30 am-1:30 pm

1 stop7h 00m

Simpson Bay Princess Juliana

mié. 5/13

2:25 pm-10:50 pm

1 stop9h 25m

$463

MilwaukeeSimpson Bay

MKE - SXM

MKESXM

Milwaukee-Mitchell

mié. 4/22

5:40 am-1:30 pm

1 stop6h 50m

Simpson Bay Princess Juliana

mié. 4/29

2:25 pm-10:50 pm

1 stop9h 25m

$498

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

Other information

What is the cheapest month to fly to Caribbean?

In general, September 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 $315. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Milwaukee, when ticket prices are also cheap, with an average price of $317.

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 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 $444 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 $334 on momondo.

What cabin class options are available on Milwaukee-Mitchell to Caribbean flights?

There is only 1 cabin class available to choose from on Milwaukee-Mitchell to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Milwaukee to Caribbean flights?

No. A direct flight is the cheapest option for a flight between Milwaukee to Caribbean.

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	4h 35m
Direct flights	Mon and Fri
Airports in Caribbean	195 airports

The fastest flight from Milwaukee to Caribbean takes 4h 35m

Direct flights go from Milwaukee to Caribbean on Monday and Friday. There are no airlines offering direct flights.

There are 195 airports in Caribbean. From Milwaukee there are direct flights to Punta Cana (PUJ).

Search flight deals

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 March 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 (69.23% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (7.69%), Boeing 737 MAX 9 (7.69%), and Boeing 737 (5.77%).

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 8,353 reviews	Search Delta flights
Frontier	PriceFrom $156	Free Cancellation	Rating 5.7 3,013 reviews	Search Frontier flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 9,500 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $219	Free Cancellation	Rating 6.3 8,552 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,519 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,334 reviews	Search Southwest flights
Sun Country Air	PriceFrom $547	Free Cancellation	Rating 6.8 339 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.