How to travel from Milwaukee to San Juan on the cheap

How to travel from Milwaukee to San Juan on the cheap
Photo: iStock
By Hoodline - Published on November 11, 2019.

If you're looking to escape to the tropics, head to San Juan, Puerto Rico, the destination with the top spot on the New York Times' list of places to visit in 2019. The island's capital and largest city faces the Atlantic Ocean, and it has plenty to offer. Plan to visit both the Isla Verde resort strip, known for its bars, nightclubs and casinos and Old San Juan, which features colorful Spanish colonial buildings, cobble-stoned streets and 16th-century landmarks. There is also the Paseo de la Princesa bayside promenade, a number of imposing fortresses and the close proximity to El Yunque National Forest, all of which are worth visiting.

Whether you’re trying to escape ASAP or you’re looking to plan ahead based on the cheapest fares, take a look at these forthcoming flights between Milwaukee and San Juan, which we pulled from travel site Skyscanner.

We've also included popular hotels, restaurants and attractions in San Juan to get you excited about your next excursion. (Prices and availability are current as of publication and subject to change.)

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Flight deals to San Juan

Currently, the cheapest flights between Milwaukee and San Juan are if you leave on Dec. 11 and return from Puerto Rico on Dec. 14. Frontier Airlines currently has tickets for $273, roundtrip.

There are also deals to be had in February. If you fly out of Milwaukee on Feb. 7 and return from San Juan on Feb. 10, Frontier Airlines can get you there and back for $308 roundtrip.

Top San Juan hotels

To help plan your stay, here are some of San Juan's top-rated hotels, according to Skyscanner, that we selected based on price, proximity to things to do and customer satisfaction.

Hotel El Convento (100 Cristo St. Old, San Juan)

Photo: Trip by Skyscanner

If you're looking to treat yourself, consider Hotel El Convento. The hotel has a 4.9-star rating on Skyscanner, and rooms are currently available for $280/night.

This boutique hotel offers convenient access to several noteworthy attractions, including the San Juan Bautista Cathedral, Puerta de San Juan and La Fortaleza Palacio de Santa Catalina.

The Marriott San Juan Resort & Stellaris Casino (1309 Ashford Ave.)

Photo: Trip by Skyscanner

There's also the 4.7-star rated The Marriott San Juan Resort & Stellaris Casino, which has rooms for $261/night.

This beachfront resort is within close proximity of Plaza del Mercado, Condado Beach and the Puerto Rico Convention Center.

La Concha Resort: A Renaissance Hotel (1077 Ashford Ave.)

Photo: Trip by Skyscanner

A third option is La Concha Resort: A Renaissance Hotel, which has a 4.6-star rating on Skyscanner and rooms going for $209/night.

"As soon as you step into La Concha, it's breathtaking. The food, beach and pools are great! Family friendly, and it has a great nightlife," wrote reviewer Sofia. 

Featured San Juan restaurants

If you're looking to snag a bite at one of San Juan's many quality eateries, here are a few popular culinary destinations from Skyscanner's listings that will help keep you satiated.

Santaella (219 Calle Canals)

Photo: Trip by Skyscanner

If you're looking for a local favorite, head to Santaella, which has an average of five stars out of 10 reviews on Skyscanner.

"Santaella celebrates the roots of the island's comida criolla, and incorporates techniques, flavors and fusions from around the world into its food," wrote "Santaella will elevate and redefine your Puerto Rican dining experience."

Acapulco Taqueria Mexicana (2021 Calle Loíza)

Another popular dining destination is Acapulco Taqueria Mexicana, with five stars from six reviews.

"Started out with [the] fried cheese and it was delicious," wrote reviewer Dani. "The tacos are to die for, especially la cochinita."

Jose Enrique (176 Calle Duffaut)

Photo: Trip by Skyscanner

Also worth considering is Jose Enrique.

"Awesome local food," wrote Jasey. "BYOB, and you sometimes have to wait for a table."

Featured San Juan attractions

Not sure what to do in San Juan, besides eat and drink? Here are a couple of recommendations, provided by Skyscanner.

Old San Juan (San Juan)

Photo: Trip by Skyscanner

First up is Old San Juan.

"Old San Juan was beautiful," wrote visitor Sofia. "So much history, and great restaurants! ... I highly recommend coming here if you're interested in learning history, local food, museums and much more."

Castillo San Felipe del Morro (501 Calle Norzagaray)

Photo: Trip by Skyscanner

Castillo San Felipe del Morro is another popular destination.

Constructed in 1540 and now listed in the National Historic Register, this six-story fort hides a warren of prison cells, barracks and hallways, attacked on many occasions throughout history by both English and Dutch forces.

This story was created automatically using flight, hotel, and local attractions data, then reviewed by an editor. Click here for more about what we're doing. Got thoughts? Go here to share your feedback.