Thinking face.

Chicago, Houston, or San Francisco? Locals and Travelers Debate Which Is Best 

Whether you’re a traveler or in the market for moving to a new city, the US offers many incredible big cities. But when it comes to Chicago, Houston, and San Francisco, which is the best?

Note: Some quotes in this piece have been lightly edited for grammar.

Where It Started

Man with an excited face.
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A lucky 20-year-old took to the internet to share that he’d received a summer internship offer with a major US airline. As such, he can move to Chicago, Houston, or San Francisco. The best part? Cost is not an issue. He asked the internet for help deciding where to go, and people came through.  


Photo Credit: Depositphotos.

To help narrow things down, the intern-to-be presented a list of requirements and preferences to consider. Among the “must-haves” are safety and a solid public transit system so he can go carless. As far as preferences go, he said he’d love a vibrant local culture that’s fit for a foodie. 

Summer in the City 

Chicago skyline.
Photo Credit: Iuliia Sokolovska via

“Man, a summer in Chicago in your 20s is gonna be great,” one person excitedly commented. Another agreed that it’s the perfect season to be in Chicago, but that San Francisco is worth considering too. “Summer in San Francisco is weirdly cold but is a great city if cost is not an issue,” they said. 

Ups and Downs 

Houston, Texas skyline.
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A former Houston resident said the city was great for their career when they were there during their 30s. “I really liked the people and the broad spectrum of beliefs and experiences they brought. The food scene was amazing.” They said in the long run, the weather and sprawl led to Houston not being for them. 

Endless Summer 

Full House row of houses in San Francisco.
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While one person believes San Francisco is a better city overall, they admit it’s not really a summer city. “It’s nicer because you get moderate weather year-round,” they said. “Summer in Chicago is pretty amazing. You miss the worst part of the city – winter.” 

Ideal for Travels 

Plane landing on a runway.
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From one airline intern to another, a commenter said to choose Chicago for two reasons. Firstly, Chicago summers are much, much better than in San Francisco. Plus, in Chicago, a weekend hop to Europe is well within reach, “but from SF, both Europe and Asia are too far for a reasonable 2-day weekend trip.” 

Glory Days 

Happy young woman.
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One former University of Houston student said they lived in Houston for nine years in their 20s and had a blast. “Was a great place to live. But there were fewer people back then and fewer cars.” They said the city had warm weather, excellent big-city amenities, and was affordable.

Expensive But Worth It 

Woman with her face in money.
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“If cost actually isn’t an issue, then absolutely San Francisco,” one person recommends. “It ticks all your boxes, but it’s seriously pricey if you’re looking to rent in a safe neighborhood and have disposable income to eat out and do fun things.”


River in Chicago.
Photo Credit: Depositphotos.

“For a summer internship? Chicago, easy,” another person says. They nod to the “top tier food and art,” great weather, beaches, street festivals, and accessible transit to the airport. “You’ll have a great time.” 

Can’t Go Carless 

Scared woman behind the wheel.
Photo Credit: Depositphotos.

“Can’t live in Houston without a car,” one Texan says. “I would say San Francisco if the pay is good, Chicago if it’s not.” A Houston hater responded, “Can’t live in Houston, period, if a sense of place and quality of life remotely matter to you. That’s why I left.” 

Looking for Love 

Man touching heart.
Photo Credit: Depositphotos.

Hands down, the best city of the three is San Francisco, one person argues. While they say Chicago has excellent museums, sports, food, and people, “San Francisco has all that plus much better weather, superlative seafood, and the best wine and beer on the planet.” They also add that San Fran has a much better dating pool. 

Easy Answer 

Nerdy man holding glasses.
Photo Credit: Depositphotos.

“I’d pick Chicago,” another says. They add that they love San Francisco, but its culture doesn’t come close to what’s in Chicago. “Houston is better than most people give it credit for, but it’s a massively sprawling car-dependent city and way too humid and hot to be trying to rely on public transportation.” 

Los Angeles Dupe 

Hollywood Walk of Fame.
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There were a lot of Houston naysayers in the thread, but to one Long Islander, the city reminded them of a cheaper, more affordable Los Angeles. “Lots of sprawl and transplants with little sense of place, but I actually liked that.”  

Take It From Me 

San Francisco with the Golden Gate Bridge.
Photo Credit: Depositphotos.

Speaking from experience, one Bay Area resident said San Francisco is the answer, especially if the cost of living will not be a factor. “San Francisco has the scene you are looking for.” 

Tough To Choose 

Woman thinking.
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One 37-year-old said they’ve visited San Francisco and Chicago a few times, and it would be a tough pick. “I agree with others that the weather would be better in Chicago for the summer. Regarding safety, it may be a wash between the two, but for different reasons.” 

Fond Memories 

People holding up beers.
Photo Credit: Depositphotos.

“I had a lot of fun in Houston in my mid-20s,” one person said, reminiscing about their time in the city’s museum district. “A lot of that, granted, was spent complaining about Houston with my friends. But we had a great time.”

Source: Reddit

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Nervous man.
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The City by the Bay makes for a pretty postcard, but not all is as it seems in San Francisco. Ten San Fran residents share whether they regret living there.

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Frustrated woman.
Photo Credit: Depositphotos.

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