Travel watch: Chicago to San Juan, and back again

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 get away ASAP or you're looking to plan your trip around the future's cheapest fares, take a look at these forthcoming flights between Chicago and San Juan, which we pulled from travel site Skyscanner.

We've also included top-rated hotels, restaurants and attractions in San Juan to get you excited about your next excursion.

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Cheapest San Juan flights

The cheapest flights between Chicago and San Juan are if you leave on May 4 and return from Puerto Rico on May 8. Spirit Airlines currently has tickets for $255, roundtrip.

There are also deals to be had in April. If you fly out of Chicago on April 1 and return from San Juan on April 4, Spirit Airlines can get you there and back for $258 roundtrip.

Top San Juan hotels

To plan your accommodations, here are some of San Juan's top-rated hotels, that we selected from Skyscanner's listings based on price and customer satisfaction.

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

Photo: Trip by Skyscanner

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

This San Juan boutique hotel is located in the historical district, near the Museo del Nino's, San Juan Cathedral and the Puerta de San Juan.

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 close to the Plaza del Mercado and Condado Beach. Additional attractions include the Puerto Rico Convention Center.

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

Photo: Trip by Skyscanner

A third option is The La Concha Resort: A Renaissance Hotel. The 4.9-star hotel has rooms for $209/night.

Located in San Juan, this beachfront hotel is near Condado Beach. Other attractions include the San Juan Cathedral.

Featured San Juan food and drink

Don't miss San Juan's food scene, with plenty of popular spots to get your fill of local cuisine. Here are a few of the top-rated eateries from Skyscanner's listings.

Kasalta (1966 Mc Leary)

Photo: Trip by Skyscanner

If you're looking for a local favorite, head to Kasalta, which has an average of 4.6 stars out of 29 reviews on Skyscanner.

"It is great for breakfast even though we saw a bar and deli here as well," wrote visitor Dani.

Santaella (219 Calle Canals)

Photo: Trip by Skyscanner

Another popular dining destination is Santaella, with five stars from 10 reviews.

El Jibarito (280 Calle Sol)

Photo: Trip by Skyscanner

Finally, there's El Jibarito, with 4.9 stars from 12 reviews.

"This is San Juan dining at its best. The beans, rice and veal were highlights and the cassava sides were a particularly pleasant surprise along with the flounder," wrote Aaron.

What to see and do in San Juan

San Juan is also full of sites to visit and explore. Here are a few popular attractions to round out your trip, again from Skyscanner's listings.

Old San Juan (San Juan)

Photo: Trip by Skyscanner

First up is Old San Juan. It checks in with 4.9 stars from 152 reviews on Skyscanner.

"Old San Juan is beautiful. I highly recommend coming here if you're interested in learning about history, local food and much more," wrote visitor Sofia.

Castillo San Felipe del Morro (501 Calle Norzagaray)

Photo: Trip by Skyscanner

The Castillo San Felipe del Morro is another popular destination. It has 4.7 stars from 123 reviews.

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

The Bacardi Rum Factory (Catano)

Photo: Trip by Skyscanner

Lastly, spend some time at The Bacardi Rum Factory. It has 4.6 stars from 89 reviews on Skyscanner.

See how Bacardi is made and sample it on a tour of the Bacardi Rum Factory.

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.