Chicago and San Francisco are two of the largest metropolises in the United States.
They are gorgeous and home to a lot of history and business opportunities and share similarities when it comes to accommodating large populations.
However, the similarities stop there.
Both cities have distinct characteristics that make them stand out from one another.
Are you interested in learning how each city stacks up to the other?
Whether you are considering living in one of these cities or just want to visit, we cover everything you need to know about Chicago’s differences, pros, and cons compared to San Francisco.
Chicago Vs. San Francisco (Differences)
We will cover some of the fundamental differences between San Francisco and Chicago to help lay down the main contrasts between the two areas and how they lead to more nuanced differences.
Chicago is a midwestern city located nearly smack-dab in the middle of the country on Lake Michigan, while San Francisco is a western city near the Pacific Ocean.
Chicago has the advantage of a strategic location when dealing with both the East Coast and West Coast.
Residents also get to enjoy the lake and some Midwestern forest preserves and, of course, the cornfields just outside the city.
However, unless you really want to see Milwaulkee or St. Louis, there aren’t too many nearby major cities.
San Francisco residents can take in the San Francisco Bay as well as the nearby Pacific Ocean and Santa Cruz Mountains.
They also enjoy the West Coast mentality, and San Francisco is also closer to other major cities.
One of the most glaring differences between Chicago and San Francisco is the weather, which varies so greatly thanks to their drastically different locations on the map.
Chicago is known for its harsh winters and windy weather.
They also experience the very real lake effect, which can make cold winter and wind feel even harsher.
San Francisco, on the other hand, tends to enjoy warm, sunny days most of the year.
While San Francisco does experience winters, they usually still have an average temperature of 50 degrees in the winter months.
3. Population Density
A city’s population density refers to how many people are stuffed into one area.
Chicago is a rather large city with 2.9 million people.
However, those people have a lot of space to spread out with 234 square miles of land.
San Francisco, on the other hand, only has 0.9 million residents.
However, all 900,000 residents live in a relatively tight space of 46 square miles.
In Chicago, you may have to travel further to get to the different landmarks you want to visit.
Luckily, a relatively effective transportation system makes this feasible, even if it takes some time, and you may have to deal with crowded trains and buses on game day.
In San Francisco, things are much closer together.
However, it may take you just as long with all of the other people taking similar routes.
4. Population Diversity
Chicago offers significantly more racial diversity, but some may also argue that there’s more segregation.
At the same time, a person may feel more comfortable living in a place that offers a large community for them.
See the following race percentage based on the 2020 census:
- Caucasian: 31.4%
- Latino: 29.9%
- Black: 28.7%
- Asian: 6.9%
- Caucasian: 52.8%
- Asian: 36%
- Latino: 15.2%
- Black: 5.6%
As you can see, there are more African-Americans and Latin-Americans in Chicago compared to San Francisco, which has a large Asian community.
Do not let race discourage you from either city, though.
Both cities welcome all people.
Feel free to represent your culture proudly anywhere.
San Francisco definitely has a unique atmosphere, unlike most other cities.
It embraces a seafaring way of life that incorporates a beatnik vibe some describe as European.
There’s a large emphasis on progressive policies and clean living.
It’s a much newer city with newer artists, including a long list of painters and poets, such as Alan Ginsberg, but also the members of the Grateful Dead.
I can imagine berets and snapping fingers to politically-charged written-word poetry at organic coffee shops with glass corporate headquarters of tech companies and boats in the harbor in the background.
Chicago, on the other hand, has more processed foods, such as hot dogs and deep-dish pizza, and more business suits.
While Chicago has distinctive characteristics, it’s called the Second City thanks to its similarities to New York in its emphasis on the typical urban life that accommodates an extremely diverse population.
Chicago has an older culture that has a lot of blues talent, housing greats like Muddy Waters Buddy Guy.
I picture Chicago as the SNL skit “Da Bears” with Chris Farley mixed with rich suburbs of Home Alone and the cool and rebellious jazz of The Blues Brothers.
It’s almost impossible to encompass the complex culture of a large city in such simple terms.
Both cities have communities that accommodate just about anyone.
Cities also evolve, so don’t assume that either city won’t change somewhat over time.
Chicago Pros And Cons
Pro: Unique Landmarks
Chicago has landmarks you won’t find anywhere else, such as the enormous Willis Tower (still widely known by residents as its former name, the Sears Tower) and the art exhibit known as “The Bean” in Millenium Park.
Chicago has more museums than San Francisco but not by much (55 compared to 48).
The museums tend to be better, too, such as the Art Institute of Chicago, known for its iconic lion statues, and the Field Museum with the infamous T-Rex named Sue, but that depends on numerous factors and your own personal preferences.
Be sure to take advantage of free museum days throughout the year if you are a resident!
Con: Harsh Winters
Chicago is known for a lot of things, but great winter weather is not one of them.
Chicago residents know to expect harsh winters.
However, you do get a much higher chance of a white Christmas and the opportunity to enjoy winter activities, such as sledding.
Plus, once you become accustomed to Chicago winters, you get to scoff at San Francisco and other warmer cities when they shut down schools for an inch of snow or wear coats in 60-degree weather.
Spring and summer come with nice weather in Chicago, even if the water in Lake Michigan is cold most of the year.
(That’s not to say you can’t take an enjoyable dip in July and August.)
Chicago is widely known for its food scene.
In particular, Chicago claims to offer the best deep-dish pizza and Chicago-style hotdogs.
If in the area, be sure to visit some of the following restaurants that can fit just about any budget:
1. Gene And Jude’s
Gene and Jude’s offers the best hot dogs and fries in the country.
That’s not an opinion.
That’s a fact.
They only take cash, but you’ll get a hot dog and fries for just a couple of dollars.
Don’t ask for ketchup because they literally won’t give it to you.
You can also get tamales and soda, but that’s all they offer on the limited menu.
Go early to avoid the late-night lines on weekend evenings.
“No Seats No Ketchup No Pretense No Nonsense”
2. Al’s Beef
A somewhat overpriced place according to locals thanks to its popularity, Al’s Beef does live up to the hype.
It has won more than 150 awards and has established itself as a food icon of Chicago over the last 80 years.
In a city known for its deep-dish pizza, you won’t find any better than Pequod’s.
Pequods uses high-end ingredients and, unlike other restaurants, uniquely burns the cheese on the edge of the pan.
Honorable mentions for hot dogs and pizza include Portillo’s, Lou Malnati’s, Johnnie’s Beef, Al & Joe’s, and Giordano’s.
Chicago offers high-end dining, organic dining, and vegan dining options as well, but you’ll fare better in San Francisco if you’re looking for those items or fresh seafood.
Nonetheless, Chicago wins hands down thanks to how affordable the food is and how delicious it is.
While not the most dangerous city in the country by far, Chicago does have a reputation for crime.
It started with organized crime in the form of the mob and crooked politicians.
Many people would argue that not much has changed over the years.
There were 797 homicides in Chicago in 2021 compared to 56 homicides in San Francisco.
That’s only the homicides.
There are additional violent crimes that occur, too.
San Francisco leads Chicago in property crime, but that’s hardly a consolation.
It’s important to address the real issues happening in the city, but that shouldn’t deter you.
Most neighborhoods and suburbs are safe.
Just research your destination location before purchasing a home or choosing a hotel to ensure you stay in a safe area.
Chicago doesn’t always win, but when they do, they win big.
There was nothing more exciting in the ’90s than having the lights come down in conjunction with the iconic music at the United Center and hearing the announcer enthusiastically introduce the players of the Chicago Bulls.
The anticipation built in the crowd and the announcer got gradually louder until he finally belts out the heights and names of Pippen, Rodman, and of course, as the crowd screams, MICHAEL JORDAN!
Jordan led the Chicago Bulls to six NBA Championships in the ’90s (1991, 1992, 1993, 1996, and 1997).
The games were especially exciting to young people fascinated by the spectacle.
The legend of Chicago sports doesn’t end there.
While not the best team in the league last year, the NFL’s Chicago Bears made a statement when the large football players bust onto the scene with their famous (infamous?) display of humor and cockiness known as the Superbowl Shuffle in 1985.
Reminiscent of Babe Ruth calling his home runs, the Chicago Bears put out the video before they won the Super Bowl, which would have been embarrassing if they didn’t win (which they did, but they haven’t won again since).
More recently, the Blackhawks stunned viewers when they turned the tide in Game 6 of the 2013 Stanley Cup to tie the game in the third quarter by scoring two goals in 17 seconds with only 1:16 left in the game.
They went on to score another point and win the entire Stanley Cup.
Of course, any discussion of sports in Chicago would come up short without mention of its TWO Major League Baseball teams.
Both of these teams suffered from long-time “curses” resulting in nearly a century in the case of the White Sox (1917–2005) and more than a century for the Cubs (1908–2016) without a World Series Championship.
San Francisco Pros And Cons
Pro: Unique Landmarks
There are certain landmarks that you simply can’t find in Chicago.
It all starts when you travel into San Francisco over the iconic Golden Gate Bridge.
The beautiful red bridge has become synonymous with The Golden City and is featured in almost every television show and movie that takes place in the area, including Full House.
Furthermore, San Francisco is home to the famous Alcatraz Prison known to be inescapable and the temporary home to Al Capone (ironically from Chicago).
The prison rests on an island in San Francisco Bay, which is part of what makes it so difficult for prisoners to escape.
Only the worst of the worst and people with the greatest flight risk would become Alcatraz inmates.
Today, it’s no longer a prison but a tourist destination that covers the different famous prisoners and failed escape attempts.
Con: Cost Of Living
Chicago isn’t exactly the least expensive place to live, especially with increased property taxes.
However, it’s not nearly as expensive as San Francisco.
San Francisco is known as one of the most expensive areas in the country.
In fact, the cost of living is 101.7% higher than the rest of the country.
The greatest expense is housing with the median price of a house in San Francisco at more than $1.3 million.
It’s no wonder Danny Tanner invited two other guys to move in with him.
Pro: Business Opportunities
San Francisco is one of the hottest business markets in the country, especially in the growing tech industry.
Tech employees, including hourly tech support employees, coders, and innovators, have more tech opportunities with higher salaries in San Francisco compared to Chicago.
It’s not only the tech industry, either.
As people flock to the area, more people need healthcare and food and other goods and services that increase opportunities in other industries as well.
Pro: Warm Weather
San Francisco has pleasant weather almost the entire year.
San Francisco rarely gets snow but it will get a significant amount of rain in the winter.
If there is snowfall, it’s significantly less than a midwestern city like Chicago experiences regularly.
Just keep in mind that San Francisco also has a lot of fog in the mornings.
The sun may take some time to peek through at first, but it generally emerges.
The pleasant weather makes San Francisco the better place for outdoor activities.
With the diverse geographical features in the area, you may also notice that there are more options when it comes to outdoor activities, too.
California is known for its earthquakes, and San Francisco is no exception.
While there was a lucky 67-year quiet period between 1911 and 1979, there have been six major recent earthquakes in San Francisco with a magnitude of 5.0 or higher.
The worst earthquake to hit the area was the 7.1 magnitude earthquake on the San Andreas fault in 1989 that killed 63 people.
If moving to the San Francisco area, be sure to get earthquake insurance on your house and prepare yourself properly.
Pros: Progressive Attitude
Even large cities like Chicago still seem far behind California and other West Coast states in terms of politics and lifestyle.
San Francisco is known for being at the epicenter of progressive movements throughout history.
For example, San Francisco was home to a large LGBT+ community in the 1970s when the topic still made many people feel uncomfortable.
The city experienced a tragedy when Korean War veteran Harvey Milk became the first openly gay politician in the country.
Despite his experience, passion, and gregarious personality, a political rival shot him only ten months after his election to the San Francisco Board of Supervisors.
While tragic, the incident highlighted the struggles that honorable gay citizens experience every day.
While still far from perfect, society has come a long way, thanks in large part to Milk and San Francisco.
Look, all cities have significant traffic.
It’s part of the territory when you have a lot of people in one area.
As we mentioned earlier, San Francisco has more people in a tighter space.
Furthermore, more people commute to and from San Francisco to other cities in the Bay Area.
Traffic in San Francisco is abysmal.
The average commute in San Francisco by car takes over an hour while in Chicago, it’s about 45 minutes.
While seemingly minuscule, that’s an extra 150 minutes a week—almost three hours!
Unless you’re catching up with a book on tape or safely making personal calls during your San Francisco commute, that’s just time you’re not getting back.
Pro: The Arts
Chicago is the setting for some of the best movies in the world.
Including the Blues Brothers and Ferris Bueller’s Day Off.
Chicago also boasts the Art Institute of Chicago.
However, San Francisco tends to offer more for artists.
Whether you prefer fashion, painting, sculpture, or poetry, you’ll find support and inspiration in San Francisco.
The leader of the Beatnik movement and the San Francisco, Alan Ginsberg, lived in San Francisco for the majority of his life.
He clearly found inspiration there, as well as other artists, such as poet George Sterling.
Chicago Vs. San Francisco Comparison Results (Winners)
Weather: San Francisco
Health: San Francisco
Population density: Chicago
Business opportunities: San Francisco
Politics: San Francisco
Crime: San Francisco
Fashion and art: San Francisco
Cost of living: Chicago
Traffic: Chicago (just barely)
Happiness: it’s a tie! You can make a great life for yourself or enjoy a great vacation in either city.
Chicago suits people who enjoy the snow, sports, freshwater activities, and down-to-earth neighbors.
San Francisco suits dreamers and progressive thinkers who like to be a short drive away from the ocean and the mountains for healthy activities after work.
While both cities are expensive and have high taxes, Chicago is more manageable for the family on the budget.
Both Chicago and San Francisco offer a big-city vibe with plenty of business opportunities.
San Francisco has a much more pronounced identity that includes a progressive and artistic mentality compared to Chicago which arguably offers more diversity in terms of lifestyle and definitely the better food and sports.
Look, I’m a Chicago girl through and through, so, for me, there’s no comparison.
I like the Chicago skyline and even the winters.
If you ever do catch me in San Francisco when Chicago gets too cold, I’ll be wearing my Bears jersey proudly.
San Francisco is great to visit, but my heart belongs to Sweet Home Chicago.