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Cheap flights from Caribbean to Wisconsin from $92

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 2/11. 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

Enter your travel dates to find the best prices.
JetBlue Logo
11:15 am - 7:45 pm
SJU
-
ORD
10h 30m1 stop
JetBlue Logo
12:41 pm - 11:44 pm
ORD
-
SJU
9h 03m1 stop
$169JetBlue
Wed, Feb 11 - Wed, Mar 4
JetBlue Logo
5:22 pm - 11:10 pm
SJU
-
ORD
7h 48m1 stop
JetBlue Logo
12:41 pm - 11:44 pm
ORD
-
SJU
9h 03m1 stop
$171JetBlue
Thu, Feb 12 - Fri, Feb 27
JetBlue Logo
11:06 am - 7:36 pm
SJU
-
ORD
10h 30m1 stop
JetBlue Logo
7:45 am - 6:02 pm
ORD
-
SJU
8h 17m1 stop
$173JetBlue
Wed, Feb 4 - Sun, Feb 8
Frontier Logo
8:00 am - 10:41 am
SJU
-
ORD
28h 41m1 stop
Frontier Logo
6:03 am - 5:00 pm
ORD
-
SJU
8h 57m1 stop
$176Frontier
Wed, Jan 21 - Sat, Jan 24
Spirit Airlines Logo
4:40 pm - 11:46 pm
AUA
-
ORD
9h 06m1 stop
Spirit Airlines Logo
5:15 am - 3:35 pm
ORD
-
AUA
8h 20m1 stop
$219Spirit Airlines
Thu, Jan 22 - Sat, Jan 31
American Airlines Logo
2:47 pm - 10:53 pm
SJU
-
MKE
10h 06m1 stop
American Airlines Logo
6:37 pm - 10:40 am
MKE
-
SJU
15h 03m1 stop
$235American Airlines
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
6:00 am - 3:57 pm
SJU
-
MKE
11h 57m2 stops
American Airlines Logo
9:30 am - 9:39 pm
MKE
-
SJU
10h 09m1 stop
$240American Airlines
Thu, Jan 29 - Mon, Feb 2
Spirit Airlines Logo
5:47 pm - 11:46 pm
PUJ
-
ORD
7h 59m1 stop
Spirit Airlines Logo
7:20 am - 4:36 pm
ORD
-
PUJ
7h 16m1 stop
$243Spirit Airlines
Tue, Feb 3 - Tue, Feb 10
United Airlines Logo
2:05 am - 12:09 pm
SJU
-
MKE
12h 04m2 stops
United Airlines Logo
11:30 am - 9:00 pm
MKE
-
SJU
7h 30m1 stop
$253United Airlines
Wed, Jan 28 - Wed, Feb 4
Delta Logo
9:00 am - 6:45 pm
KIN
-
ORD
10h 45m2 stops
Delta Logo
6:50 am - 8:00 pm
ORD
-
KIN
12h 10m2 stops
$400Delta
Fri, Jan 30 - Fri, Feb 6

United Airlines flights from Caribbean to Wisconsin

Our best United Airlines deals on Caribbean to Wisconsin flight tickets
United Airlines
Jan 28
SJU2:05 amSan Juan Luis Munoz Marin Intl
12h 04m
2 stops
MKE12:09 pmMilwaukee-Mitchell
Feb 4
MKE11:30 amMilwaukee-Mitchell
7h 30m
1 stop
SJU9:00 pmSan Juan Luis Munoz Marin Intl
$253
Find similar
United Airlines
Dec 23
SJU4:52 pmSan Juan Luis Munoz Marin Intl
5h 28m
ORD8:20 pmChicago O'Hare Intl
Jan 14
ORD2:20 pmChicago O'Hare Intl
4h 40m
SJU9:00 pmSan Juan Luis Munoz Marin Intl
$256
Find similar
United Airlines
Feb 14
NAS4:05 pmNassau Intl
3h 57m
ORD7:02 pmChicago O'Hare Intl
Feb 18
ORD10:45 amChicago O'Hare Intl
3h 37m
NAS3:22 pmNassau Intl
$464
Find similar

JetBlue flights from Caribbean to Wisconsin

Our best JetBlue deals on Caribbean to Wisconsin flight tickets
JetBlue
Feb 11
SJU11:15 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:45 pmChicago O'Hare Intl
Mar 4
ORD12:41 pmChicago O'Hare Intl
9h 03m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
$169
Find similar
JetBlue
Feb 12
SJU5:22 pmSan Juan Luis Munoz Marin Intl
7h 48m
1 stop
ORD11:10 pmChicago O'Hare Intl
Feb 27
ORD12:41 pmChicago O'Hare Intl
9h 03m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
$171
Find similar
JetBlue
Feb 4
SJU11:06 amSan Juan Luis Munoz Marin Intl
10h 30m
1 stop
ORD7:36 pmChicago O'Hare Intl
Feb 8
ORD7:45 amChicago O'Hare Intl
8h 17m
1 stop
SJU6:02 pmSan Juan Luis Munoz Marin Intl
$173
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 December 18, 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

Wed 2/11

11:15 am-7:45 pm

1 stop10h 30m

Chicago O'Hare Intl

Wed 3/4

12:41 pm-11:44 pm

1 stop9h 03m

$169

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/12

5:22 pm-11:10 pm

1 stop7h 48m

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

$171

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 2/4

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Sun 2/8

7:45 am-6:02 pm

1 stop8h 17m

$173

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Wed 1/21

8:00 am-10:41 am

1 stop28h 41m

Chicago O'Hare Intl

Sat 1/24

6:03 am-5:00 pm

1 stop8h 57m

$176

OranjestadChicago

AUA - ORD

AUAORD

Oranjestad Reina Beatrix

Thu 1/22

4:40 pm-11:46 pm

1 stop9h 06m

Chicago O'Hare Intl

Sat 1/31

5:15 am-3:35 pm

1 stop8h 20m

$219

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 3/5

2:47 pm-10:53 pm

1 stop10h 06m

Milwaukee-Mitchell

Sun 3/8

6:37 pm-10:40 am

1 stop15h 03m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/29

6:00 am-3:57 pm

2 stops11h 57m

Milwaukee-Mitchell

Mon 2/2

9:30 am-9:39 pm

1 stop10h 09m

$240

Punta CanaChicago

PUJ - ORD

PUJORD

Punta Cana

Tue 2/3

5:47 pm-11:46 pm

1 stop7h 59m

Chicago O'Hare Intl

Tue 2/10

7:20 am-4:36 pm

1 stop7h 16m

$243

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-12:09 pm

2 stops12h 04m

Milwaukee-Mitchell

Wed 2/4

11:30 am-9:00 pm

1 stop7h 30m

$253

KingstonChicago

KIN - ORD

KINORD

Kingston Norman Manley

Fri 1/30

9:00 am-6:45 pm

2 stops10h 45m

Chicago O'Hare Intl

Fri 2/6

6:50 am-8:00 pm

2 stops12h 10m

$400

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 September instead. Flights to Wisconsin in September, while not as cheap as those in February, still average around $298.

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 $382 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 $286 on momondo.

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

There is only 1 cabin class 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 62% 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

Fastest flight time

3h 56m

Direct flights

Every day

Airports in Wisconsin

80 airports
The fastest flight from Caribbean to Wisconsin takes 3h 56m
Direct flights go from Caribbean to Wisconsin every day.
There are 80 airports in Wisconsin. From Caribbean there are direct flights to Chicago O'Hare Intl (ORD).
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
DeltaPriceFrom $118Free CancellationRating
7.9
8,005 reviews
Search Delta flights
Spirit AirlinesPriceFrom $182Free CancellationRating
6.3
8,190 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $215Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
American AirlinesPriceFrom $235Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
SouthwestPriceFrom $305Free CancellationRating
7.9
4,250 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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