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Cheap flights from Caribbean to Wisconsin from $79

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Wisconsin departing on 8/22. 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 Caribbean to Wisconsin

Cheap round-trip flights

Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Spirit Airlines Logo
5:05 am - 9:48 pmORD-SJU
15h 43m1 stop
$148Spirit Airlines
Find Deal
Fri, Aug 22 - Mon, Aug 25
Spirit Airlines Logo
10:16 pm - 9:22 amSJU-ORD
12h 06m1 stop
Spirit Airlines Logo
5:05 am - 9:48 pmORD-SJU
15h 43m1 stop
$172Spirit Airlines
Find Deal
Fri, Aug 22 - Sun, Aug 24
Southwest Logo
4:05 pm - 11:00 pmSJU-MKE
7h 55m1 stop
Southwest Logo
12:20 pm - 11:30 pmMKE-SJU
10h 10m1 stop
$175Southwest
Find Deal
Fri, Sep 12 - Fri, Sep 26
American Airlines Logo
2:35 pm - 11:30 pmSJU-MKE
9h 55m2 stops
American Airlines Logo
5:00 am - 5:05 pmMKE-SJU
10h 05m2 stops
$225American Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
American Airlines Logo
3:50 pm - 12:09 amSJU-MKE
9h 19m1 stop
American Airlines Logo
6:23 pm - 12:47 pmMKE-SJU
17h 24m2 stops
$232American Airlines
Find Deal
Thu, Sep 25 - Mon, Sep 29
Southwest Logo
5:50 am - 3:45 pmSJU-MKE
10h 55m1 stop
Southwest Logo
6:00 am - 8:45 pmMKE-SJU
13h 45m2 stops
$245Southwest
Find Deal
Fri, Sep 12 - Fri, Sep 26
Delta Logo
1:50 pm - 7:03 pmSJU-MKE
7h 13m1 stop
Delta Logo
7:00 am - 5:10 pmMKE-SJU
8h 10m1 stop
$255Delta
Find Deal
Thu, Dec 4 - Wed, Dec 10
Delta Logo
5:41 pm - 11:48 pmSJU-MKE
7h 07m1 stop
Delta Logo
5:40 am - 4:31 pmMKE-SJU
9h 51m1 stop
$295Delta
Find Deal
Sat, Sep 20 - Sun, Sep 28
United Airlines Logo
1:05 am - 11:24 amSJU-MKE
11h 19m2 stops
United Airlines Logo
6:05 am - 3:40 pmMKE-SJU
7h 35m1 stop
$345United Airlines
Find Deal
Wed, Oct 29 - Mon, Nov 3
United Airlines Logo
4:35 pm - 11:15 pmPUJ-ORD
7h 40m1 stop
United Airlines Logo
9:28 am - 3:05 pmORD-PUJ
4h 37mnonstop
$365United Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 28

JetBlue flights from Caribbean to Wisconsin

Our best JetBlue deals on Caribbean to Wisconsin flight tickets
JetBlue
Sep 24
BQN5:01 amAguadilla Borinquen
8h 41m
1 stop
ORD12:42 pmChicago O'Hare Intl
Oct 15
ORD9:42 amChicago O'Hare Intl
15h 49m
2 stops
BQN2:31 amAguadilla Borinquen
$406
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JetBlue
Aug 12
NAS3:50 pmNassau Intl
7h 38m
1 stop
ORD10:28 pmChicago O'Hare Intl
Aug 17
ORD6:15 amChicago O'Hare Intl
7h 30m
1 stop
NAS2:45 pmNassau Intl
$778
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Frontier flights from Caribbean to Wisconsin

Our best Frontier deals on Caribbean to Wisconsin flight tickets
Frontier
Aug 12
SJU3:40 amSan Juan Luis Munoz Marin Intl
7h 34m
1 stop
ORD10:14 amChicago O'Hare Intl
Sep 13
ORD8:00 amChicago O'Hare Intl
17h 34m
1 stop
SJU2:34 amSan Juan Luis Munoz Marin Intl
$248
Find similar
Frontier
Aug 28
SJU3:21 pmSan Juan Luis Munoz Marin Intl
9h 33m
1 stop
ORD11:54 pmChicago O'Hare Intl
Aug 30
ORD7:46 pmChicago O'Hare Intl
12h 13m
1 stop
SJU8:59 amSan Juan Luis Munoz Marin Intl
$258
Find similar
Frontier
Sep 3
BQN3:32 amAguadilla Borinquen
17h 12m
1 stop
ORD7:44 pmChicago O'Hare Intl
Sep 20
ORD8:00 amChicago O'Hare Intl
17h 27m
1 stop
BQN2:27 amAguadilla Borinquen
$265
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to Wisconsin 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 7, 2025.
Use the filters below to find and compare flights from Caribbean to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/22

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Mon 8/25

5:05 am-9:48 pm

1 stop15h 43m

$148

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 8/22

10:16 pm-9:22 am

1 stop12h 06m

Chicago O'Hare Intl

Sun 8/24

5:05 am-9:48 pm

1 stop15h 43m

$172

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 9/12

4:05 pm-11:00 pm

1 stop7h 55m

Milwaukee-Mitchell

Fri 9/26

12:20 pm-11:30 pm

1 stop10h 10m

$175

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 10/30

2:35 pm-11:30 pm

2 stops9h 55m

Milwaukee-Mitchell

Mon 11/3

5:00 am-5:05 pm

2 stops10h 05m

$225

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 9/25

3:50 pm-12:09 am

1 stop9h 19m

Milwaukee-Mitchell

Mon 9/29

6:23 pm-12:47 pm

2 stops17h 24m

$232

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 9/12

5:50 am-3:45 pm

1 stop10h 55m

Milwaukee-Mitchell

Fri 9/26

6:00 am-8:45 pm

2 stops13h 45m

$245

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 12/4

1:50 pm-7:03 pm

1 stop7h 13m

Milwaukee-Mitchell

Wed 12/10

7:00 am-5:10 pm

1 stop8h 10m

$255

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 9/20

5:41 pm-11:48 pm

1 stop7h 07m

Milwaukee-Mitchell

Sun 9/28

5:40 am-4:31 pm

1 stop9h 51m

$295

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 10/29

1:05 am-11:24 am

2 stops11h 19m

Milwaukee-Mitchell

Mon 11/3

6:05 am-3:40 pm

1 stop7h 35m

$345

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Thu 9/18

4:35 pm-11:15 pm

1 stop7h 40m

Chicago O'Hare Intl

Sun 9/28

9:28 am-3:05 pm

Nonstop4h 37m

$365

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 Wisconsin from

How to get the cheapest flight ticket from Caribbean to Wisconsin

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 Wisconsin?

If you aren’t able to travel during the month of February, then book flights to Wisconsin from Caribbean during January instead. Flights to Wisconsin in January, while not as cheap as those in February, still average around $321.

What is the cheapest day to depart on your flight to Wisconsin?

The cheapest day to depart from Caribbean to Wisconsin is on a Thursday. Travelers who choose to depart for Wisconsin on a Thursday will often find tickets for as low as $331. The most expensive day to fly to Wisconsin is Sunday, with ticket prices averaging around $624.

What is the cheapest time of day to depart on your flight to Wisconsin?

Our most recent data shows that the best time of day to fly to Wisconsin is in the evening. Flights from Caribbean to Wisconsin during this time can be as low as $404. Flights at noon are often more expensive with an average ticket price of $429.

What is the cheapest Caribbean to Wisconsin flight route?

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

How far in advance should I book a flight to Wisconsin?

You are more likely to see cheaper flights to Wisconsin from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Wisconsin for around $381 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Wisconsin from Caribbean for as low as $270 on momondo.

What cabin class options are available on Caribbean to Wisconsin flights?

There are 1 cabin classes available to choose from on Caribbean to Wisconsin 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 Caribbean to Wisconsin flights?

You could potentially save up to 58% on your flight if you consider stops on a Caribbean to Wisconsin flight.

Cheap Caribbean to Wisconsin flight deals and tips

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

Best Price Found

$79

Fastest flight time

3h 56m

Direct flights

Every day

Airports in Wisconsin

3 airports
The best one-way flight to Wisconsin from Caribbean in the past 72 hours is $79. The best round-trip flight deal from Caribbean to Wisconsin found on momondo in the last 72 hours is $148.
The fastest flight from Caribbean to Wisconsin takes 3h 56m
Direct flights go from Caribbean to Wisconsin every day.
There are 3 airports near Wisconsin: Chicago O'Hare Intl (ORD), Milwaukee-Mitchell (MKE), Minneapolis St Paul (MSP)
Search flight deals

  • When did momondo last update prices for flights from Caribbean to Wisconsin?

    Prices for flights from Caribbean to Wisconsin are refreshed on a daily basis.

  • How many operators does momondo search for flights from Caribbean to Wisconsin?

  • How old do you have to be to fly from Caribbean to Wisconsin?

    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 Caribbean to Wisconsin.

  • What documentation or ID do you need to fly to Wisconsin?

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

Best airlines flying from Caribbean to Wisconsin

Compare and see reviews for airlines that fly from Caribbean to Wisconsin with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $215Free CancellationRating
7.4
8,917 reviews
Search United Airlines flights
DeltaPriceFrom $265Free CancellationRating
8.0
7,985 reviews
Search Delta flights
American AirlinesPriceFrom $265Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $323Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Caribbean to Wisconsin for you.

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

momondo does allow users to show only those flights to Wisconsin from Caribbean which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Caribbean and Wisconsin by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Caribbean to Wisconsin right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Wisconsin from Caribbean. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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