What is the cheapest airline that flies from Puerto Rico to Wisconsin?

Southwest, Sun Country Air, and Frontier are the most popular carriers operating from Puerto Rico to Wisconsin

What airlines fly to Wisconsin?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Wisconsin from Puerto Rico according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Wisconsin. Keep in mind that there are 4 different airlines that fly to Wisconsin on a routine basis, so you have a few additional options to choose from.

How many flights depart from Puerto Rico to Wisconsin on average per week?

The number of flights available between Puerto Rico and Wisconsin is 40 per week as of September 2026. The most frequent departure day is Mon, with 15% of weekly flights leaving on this day.

How long is the flight from Puerto Rico to Wisconsin?

Average flight duration from Puerto Rico to Wisconsin depends on which airport you fly into and out of. Flying from San Juan to Milwaukee is 7h 19m on average, while flying from Culebra to Milwaukee is 12h 51m on average. Milwaukee is the most popular airport in Wisconsin.

When did momondo last update prices for flights from Puerto Rico to Wisconsin?

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

How many operators does momondo search for flights from Puerto Rico to Wisconsin?

The number of operators available for flights from Puerto Rico to Wisconsin is 7 as of September 2026.

How old do you have to be to fly from Puerto Rico to Wisconsin?

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 Puerto Rico to Wisconsin.

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

The travel and health documents you'll need for your trip to Wisconsin may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Wisconsin. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$115 Cheap Flights from Puerto Rico to Wisconsin in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Puerto Rico to Wisconsin

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Recent round-trip flight deals from Puerto Rico to Wisconsin

Enter your travel dates to find the best prices.

7:00 am - 2:45 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

8h 45m1 stop Fort Lauderdale

7:11 am - 1:34 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

29h 23m1 stop Fort Lauderdale

$198Frontier

Thu, Sep 24 - Sat, Oct 3

7:00 am - 2:45 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

8h 45m1 stop Fort Lauderdale

7:11 am - 1:31 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

29h 20m1 stop Fort Lauderdale

$201Frontier

Thu, Sep 24 - Wed, Oct 7

2:53 pm - 7:29 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 36mnonstop

8:13 am - 2:03 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 50mnonstop

$217American Airlines

Wed, Oct 14 - Sat, Oct 17

2:53 pm - 7:29 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 36mnonstop

8:13 am - 2:03 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 50mnonstop

$217American Airlines

Sat, Oct 10 - Sat, Oct 24

3:56 pm - 8:05 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 09mnonstop

2:16 pm - 8:00 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 44mnonstop

$232United Airlines

Sat, Sep 26 - Thu, Oct 29

4:55 pm - 11:31 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

7h 36m1 stop Washington, D.C. Dulles Intl

2:16 pm - 8:00 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 44mnonstop

$237United Airlines

Sat, Sep 26 - Thu, Oct 29

2:59 pm - 9:49 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell

7h 50m1 stop Atlanta Hartsfield-Jackson

5:30 am - 4:49 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl

10h 19m1 stop Atlanta Hartsfield-Jackson

$238Delta

Thu, Oct 1 - Mon, Oct 5

4:15 pm - 8:46 pmSJU San Juan Luis Munoz Marin Intl-MSP Minneapolis St Paul

5h 31mnonstop

9:00 am - 3:15 pmMSP Minneapolis St Paul-SJU San Juan Luis Munoz Marin Intl

5h 15mnonstop

$265Sun Country Air

Sat, Oct 10 - Sat, Oct 17

4:15 pm - 8:46 pmSJU San Juan Luis Munoz Marin Intl-MSP Minneapolis St Paul

5h 31mnonstop

9:00 am - 4:14 pmMSP Minneapolis St Paul-SJU San Juan Luis Munoz Marin Intl

5h 14mnonstop

$319Sun Country Air

Sat, Oct 10 - Sat, Nov 14

2:30 pm - 8:05 pmSJU San Juan Luis Munoz Marin Intl-MKE Milwaukee-Mitchell

6h 35m1 stop Detroit Metropolitan Wayne County

5:30 am - 4:49 pmMKE Milwaukee-Mitchell-SJU San Juan Luis Munoz Marin Intl

10h 19m1 stop Atlanta Hartsfield-Jackson

$366Delta

Sat, Sep 26 - Mon, Sep 28

Recent last minute flight deals from Puerto Rico to Wisconsin

Enter your travel dates to find the best prices.

7:14 pm - 11:27 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 13mnonstop

12:44 am - 6:44 amORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

5h 00mnonstop

$171Frontier

Wed, Sep 2 - Sat, Sep 5

7:14 pm - 11:27 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 13mnonstop

12:44 am - 6:44 amORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

5h 00mnonstop

$172Frontier

Wed, Sep 2 - Sun, Sep 6

2:55 pm - 12:59 amSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

11h 04m1 stop Houston George Bush Intcntl

8:55 am - 2:44 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 49mnonstop

$256United Airlines

Sat, Sep 5 - Sun, Sep 6

12:55 am - 5:00 amSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 05mnonstop

5:20 pm - 11:15 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 55mnonstop

$257American Airlines

Fri, Sep 4 - Sun, Sep 6

12:55 am - 5:00 amSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 05mnonstop

5:20 pm - 11:15 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 55mnonstop

$257American Airlines

Wed, Sep 2 - Sun, Sep 6

3:56 pm - 8:05 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 09mnonstop

5:30 am - 3:42 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

9h 12m1 stop Houston George Bush Intcntl

$287United Airlines

Fri, Sep 4 - Mon, Sep 7

9:42 am - 2:24 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

29h 42m1 stop Fort Lauderdale

12:44 am - 6:44 amORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

5h 00mnonstop

$394Multiple Airlines

Fri, Sep 4 - Sun, Sep 6

6:35 am - 12:50 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

7h 15m1 stop Fort Lauderdale

2:35 pm - 11:22 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

7h 47m1 stop Fort Lauderdale

$404Multiple Airlines

Tue, Sep 1 - Fri, Sep 4

7:00 am - 2:09 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

8h 09m1 stop Atlanta Hartsfield-Jackson

5:30 am - 1:42 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

7h 12m1 stop Atlanta Hartsfield-Jackson

$416Delta

Wed, Sep 2 - Sun, Sep 6

7:00 am - 2:09 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

8h 09m1 stop Atlanta Hartsfield-Jackson

5:30 am - 1:42 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

7h 12m1 stop Atlanta Hartsfield-Jackson

$416Delta

Wed, Sep 2 - Sun, Sep 6

Recent direct flight deals from Puerto Rico to Wisconsin

Enter your travel dates to find the best prices.

2:53 pm - 7:29 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 36mnonstop

8:13 am - 2:03 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 50mnonstop

$217American Airlines

Sat, Oct 10 - Sat, Oct 24

2:53 pm - 7:29 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 36mnonstop

8:13 am - 2:03 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 50mnonstop

$217American Airlines

Wed, Oct 14 - Sat, Oct 17

3:56 pm - 8:05 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 09mnonstop

2:16 pm - 8:00 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 44mnonstop

$232United Airlines

Sat, Sep 26 - Thu, Oct 29

7:00 pm - 10:28 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 28mnonstop

11:50 pm - 6:36 amORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 46mnonstop

$249Frontier

Fri, Dec 25 - Fri, Jan 1

3:55 am - 7:16 amSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 21mnonstop

7:53 pm - 2:35 amORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 42mnonstop

$253Frontier

Sun, Nov 22 - Fri, Nov 27

4:15 pm - 8:46 pmSJU San Juan Luis Munoz Marin Intl-MSP Minneapolis St Paul

5h 31mnonstop

9:00 am - 3:15 pmMSP Minneapolis St Paul-SJU San Juan Luis Munoz Marin Intl

5h 15mnonstop

$265Sun Country Air

Sat, Oct 10 - Sat, Oct 17

3:56 pm - 8:05 pmSJU San Juan Luis Munoz Marin Intl-ORD Chicago O'Hare Intl

5h 09mnonstop

8:55 am - 2:44 pmORD Chicago O'Hare Intl-SJU San Juan Luis Munoz Marin Intl

4h 49mnonstop

$292United Airlines

Fri, Sep 18 - Mon, Oct 5

4:15 pm - 8:46 pmSJU San Juan Luis Munoz Marin Intl-MSP Minneapolis St Paul

5h 31mnonstop

9:00 am - 4:14 pmMSP Minneapolis St Paul-SJU San Juan Luis Munoz Marin Intl

5h 14mnonstop

$319Sun Country Air

Sat, Oct 10 - Sat, Nov 14

5:15 pm - 9:10 pmSJU San Juan Luis Munoz Marin Intl-MSP Minneapolis St Paul

5h 55mnonstop

9:00 am - 4:10 pmMSP Minneapolis St Paul-SJU San Juan Luis Munoz Marin Intl

5h 10mnonstop

$444Delta

Tue, Jan 12 - Thu, Jan 21

3:20 pm - 7:15 pmSJU San Juan Luis Munoz Marin Intl-MSP Minneapolis St Paul

5h 55mnonstop

7:00 am - 2:15 pmMSP Minneapolis St Paul-SJU San Juan Luis Munoz Marin Intl

5h 15mnonstop

$444Delta

Tue, Jan 12 - Mon, Jan 25

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American Airlines flights from Puerto Rico to Wisconsin

Our best American Airlines deals on Puerto Rico to Wisconsin flight tickets

American Airlines

Oct 10

SJU2:53 pmSan Juan Luis Munoz Marin Intl

5h 36m

ORD7:29 pmChicago O'Hare Intl

Oct 24

ORD8:13 amChicago O'Hare Intl

4h 50m

SJU2:03 pmSan Juan Luis Munoz Marin Intl

$217

American Airlines

Oct 10

SJU2:53 pmSan Juan Luis Munoz Marin Intl

5h 36m

ORD7:29 pmChicago O'Hare Intl

Oct 11

ORD6:29 amChicago O'Hare Intl

15h 28m

1 stop

SJU10:57 pmSan Juan Luis Munoz Marin Intl

$220

American Airlines

Nov 5

SJU3:52 pmSan Juan Luis Munoz Marin Intl

5h 38m

ORD7:30 pmChicago O'Hare Intl

Nov 9

ORD7:50 pmChicago O'Hare Intl

12h 55m

1 stop

SJU10:45 amSan Juan Luis Munoz Marin Intl

$222

United Airlines flights from Puerto Rico to Wisconsin

Our best United Airlines deals on Puerto Rico to Wisconsin flight tickets

United Airlines

Sep 26

SJU3:56 pmSan Juan Luis Munoz Marin Intl

5h 09m

ORD8:05 pmChicago O'Hare Intl

Oct 29

ORD2:16 pmChicago O'Hare Intl

4h 44m

SJU8:00 pmSan Juan Luis Munoz Marin Intl

$232

United Airlines

Sep 24

SJU3:56 pmSan Juan Luis Munoz Marin Intl

5h 09m

ORD8:05 pmChicago O'Hare Intl

Sep 28

ORD5:00 amChicago O'Hare Intl

7h 45m

1 stop

SJU1:45 pmSan Juan Luis Munoz Marin Intl

$282

United Airlines

Jan 21

BQN1:09 amAguadilla Borinquen

9h 53m

1 stop

ORD9:02 amChicago O'Hare Intl

Jan 22

ORD12:40 pmChicago O'Hare Intl

9h 17m

1 stop

BQN11:57 pmAguadilla Borinquen

$431

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/24

7:00 am-2:45 pm

1 stop8h 45m

Chicago O'Hare Intl

Sat 10/3

7:11 am-1:34 pm

1 stop29h 23m

$198

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl

SJUORD

San Juan Luis Munoz Marin Intl

Thu 9/24

7:00 am-2:45 pm

1 stop8h 45m

Chicago O'Hare Intl

Wed 10/7

7:11 am-1:31 pm

1 stop29h 20m

$201

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl

SJUORD

San Juan Luis Munoz Marin Intl

Wed 10/14

2:53 pm-7:29 pm

Nonstop5h 36m

Chicago O'Hare Intl

Sat 10/17

8:13 am-2:03 pm

Nonstop4h 50m

$217

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl

SJUORD

San Juan Luis Munoz Marin Intl

Sat 10/10

2:53 pm-7:29 pm

Nonstop5h 36m

Chicago O'Hare Intl

Sat 10/24

8:13 am-2:03 pm

Nonstop4h 50m

$217

Quickest round-trip

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl

SJUORD

San Juan Luis Munoz Marin Intl

Sat 9/26

3:56 pm-8:05 pm

Nonstop5h 09m

Chicago O'Hare Intl

Thu 10/29

2:16 pm-8:00 pm

Nonstop4h 44m

$232

San JuanChicago

SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl

SJUORD

San Juan Luis Munoz Marin Intl

Sat 9/26

4:55 pm-11:31 pm

1 stop7h 36m

Chicago O'Hare Intl

Thu 10/29

2:16 pm-8:00 pm

Nonstop4h 44m

$237

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 10/1

2:59 pm-9:49 pm

1 stop7h 50m

Milwaukee-Mitchell

Mon 10/5

5:30 am-4:49 pm

1 stop10h 19m

$238

San JuanMinneapolis

SJU San Juan Luis Munoz Marin Intl - MSP Minneapolis St Paul

SJUMSP

San Juan Luis Munoz Marin Intl

Sat 10/10

4:15 pm-8:46 pm

Nonstop5h 31m

Minneapolis St Paul

Sat 10/17

9:00 am-3:15 pm

Nonstop5h 15m

$265

San JuanMinneapolis

SJU San Juan Luis Munoz Marin Intl - MSP Minneapolis St Paul

SJUMSP

San Juan Luis Munoz Marin Intl

Sat 10/10

4:15 pm-8:46 pm

Nonstop5h 31m

Minneapolis St Paul

Sat 11/14

9:00 am-4:14 pm

Nonstop5h 14m

$319

San JuanMilwaukee

SJU San Juan Luis Munoz Marin Intl - MKE Milwaukee-Mitchell

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 9/26

2:30 pm-8:05 pm

1 stop6h 35m

Milwaukee-Mitchell

Mon 9/28

5:30 am-4:49 pm

1 stop10h 19m

$366

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 Puerto Rico 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

Prices

Airlines

Other information

What is the cheapest month to fly to Wisconsin?

If you aren’t able to travel during the month of January, then book flights to Wisconsin from Puerto Rico during February instead. Flights to Wisconsin in February, while not as cheap as those in January, still average around $294.

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

You are more likely to see cheaper flights to Wisconsin from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Wisconsin for around $383 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Wisconsin from Puerto Rico for as low as $215 on momondo.

Can stopping save me money on Puerto Rico to Wisconsin flights?

You could potentially save up to 14% on your flight if you consider stops on a Puerto Rico to Wisconsin flight.

Cheap Puerto Rico to Wisconsin flight deals and tips

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

Best Price Found	$115
Fastest flight time	5h 09m
Direct flights	Every day
Airports in Wisconsin	80 airports

The best one-way flight to Wisconsin from Puerto Rico in the past 72 hours is $115. The best round-trip flight deal from Puerto Rico to Wisconsin found on momondo in the last 72 hours is $198.

The fastest flight from Puerto Rico to Wisconsin takes 5h 09m

Direct flights go from Puerto Rico to Wisconsin every day.

There are 80 airports in Wisconsin. From Puerto Rico there are direct flights to Chicago O'Hare Intl (ORD), Minneapolis St Paul (MSP).

Search flight deals

Frequently asked questions about flying from Puerto Rico to Wisconsin

When did momondo last update prices for flights from Puerto Rico to Wisconsin?
Prices for flights from Puerto Rico to Wisconsin are refreshed on a daily basis.
How many operators does momondo search for flights from Puerto Rico to Wisconsin?
The number of operators available for flights from Puerto Rico to Wisconsin is 7 as of September 2026.
How old do you have to be to fly from Puerto Rico to Wisconsin?
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 Puerto Rico to Wisconsin.
What documentation or ID do you need to fly to Wisconsin?
The travel and health documents you'll need for your trip to Wisconsin may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Wisconsin. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Puerto Rico to Wisconsin

Compare and see reviews for airlines that fly from Puerto Rico to Wisconsin with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $118	Free Cancellation	Rating 7.8 8,538 reviews	Search Delta flights
United Airlines	PriceFrom $235	Free Cancellation	Rating 7.4 10,157 reviews	Search United Airlines flights
American Airlines	PriceFrom $235	Free Cancellation	Rating 7.1 12,023 reviews	Search American Airlines flights
Southwest	PriceFrom $256	Free Cancellation	Rating 8.0 4,191 reviews	Search Southwest flights

Why use momondo?

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

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 Wisconsin from Puerto Rico.

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

Yes. momondo enables you to select and highlight flights to Wisconsin from Puerto Rico with this policy.

How can momondo help me find flights from Puerto Rico to Wisconsin?

Once you have performed a search for Puerto Rico to Wisconsin 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 Puerto Rico to Wisconsin right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Wisconsin, momondo offers a useful price alert feature which will track prices for flights to Wisconsin from Puerto Rico and alert you when they change.