Travel watch: Chicago to San Diego, and back again

Have you been craving a California getaway, without the congestion of LA? San Diego offers plenty of sandy beaches and sunny days, with an even more laid-back vibe and the best border town tacos you can find.

The city's top-rated local craft brewing industry is a major draw, along with the famous San Diego Zoo, other amusement parks, and many historic sites from the city's Spanish and Mexican heritage. And San Diego's deep-water harbor supports a wide range of coastal activities, including sight-seeing cruises, whale-watching, and Southern California's largest sport fishing fleet.

Thankfully, there are plenty of regular, relatively inexpensive flights between Chicago and San Diego. We pulled from travel site Skyscanner to provide you with a short list of flights and hotels handpicked with the trendy adventurer in mind.

(Hoodline offers data-driven analysis of local happenings and trends across cities. Links included in the articles may earn Hoodline a commission on clicks and transactions. Prices and availability are subject to change.)

Flight deals to San Diego




Currently, the cheapest flights between Chicago and San Diego are if you leave on April 29 and return from California on May 2. Spirit Airlines currently has roundtrip tickets for $155.

There are also deals to be had in May. If you fly out of Chicago on May 1 and return from San Diego on May 4, Spirit Airlines can get you there and back for $156 roundtrip.

Top San Diego hotels




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

The Hotel del Coronado (1500 Orange Ave.)

Photo: Trip by Skyscanner

If you're looking to splurge on top quality, consider The Hotel del Coronado. The hotel has a 4.6-star rating on Skyscanner, and rooms are currently available for $290.

The Omni La Costa Resort and Spa (2100 Costa Del Mar Road)

Photo: Trip by Skyscanner

There's also the 4.7-star rated The Omni La Costa Resort and Spa, which has rooms for $249/night.

The U.S. Grant (326 Broadway)


Photo: Trip by Skyscanner

A third option is The U.S. Grant. The 4.7-star hotel has rooms for $159/night.

Set in the heart of San Diego, this hotel is close to the Westfield Horton Plaza, Petco Park, as well as the San Diego Convention Center. Other attractions include the San Diego Zoo.

Featured San Diego food and drink




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

Extraordinary Desserts (2929 Fifth Ave.)

Photo: Trip by Skyscanner

First things first: dessert. For a popular option, check out Extraordinary Desserts, which has an average of 4.7 stars out of 160 reviews on Skyscanner.

"This is a very nice place to hang out with friends and share some beautifully decorated treats. I love the fresh fruit tarts," wrote visitor Roque.

The Prado at Balboa Park (1549 El Prado)

Photo: Trip by Skyscanner

One of San Diego's most popular restaurants is The Prado at Balboa Park, with 4.6 stars from 133 reviews.

"There is a breeze blowing even on the hottest days, and you might even get to watch a wedding take place in the garden below if you sit outside," wrote reviewer Sandra.

Featured local attractions




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

The San Diego Zoo (2920 Zoo Drive)

Photo: Trip by Skyscanner

First up is The San Diego Zoo, with 4.8 stars from 1,036 reviews.

The San Diego Zoo houses more than 4,000 animals from roughly 800 species. At more than 100 acres, the zoo offers exhibits that run the gamut of the world's ecosystems: rain forest, savanna, desert and more.

Balboa Park (1549 El Prado)

Photo: Trip by Skyscanner

Balboa Park is another popular destination, with 4.8 stars from 815 reviews.

Along with countless green spaces and gardens, the park is home to multiple museums, shops, restaurants and, most famously, the San Diego Zoo.

The Gaslamp Quarter (614 Fifth Ave.)

Photo: Trip by Skyscanner

Finally, spend some time at The Gaslamp Quarter. It checks in with 4.6 stars out of 578 reviews on Skyscanner.
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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.