San Francisco, Travel, USA

Chicago vs. San Francisco

Champion Boxer With Sign
Let’s get ready to…RRRRrrrruuuummbbllleeee!!!!

Chicago and San Francisco both hold a dear place in my heart. It’s been fascinating for me to see how the different cities have evolved.  The sometimes subtle, sometimes not, differences between the two. Each city offers a different day to day lifestyle, and I’m loving walking in the San Franciscian shoes (even though my two pitiful knees “San” and “Fran” are begging me to stop). We could learn a lot of from San Francisco, and they could learn a lot from Chicago. Who will take the belt?!

Chicago vs San Francisco

1. Transit – Welcome to the land of scooters and trolley cars.

This was the most obvious for me to talk about first. As a Chicago commuter, I feel pretty good about navigating public transit as an enjoyable way to get around. The CTA (Chicago Transit Authority) and MUNI (San Francisco Municipal Railway) share many similar qualities – the ability to accept cash fare, along with RFI cards. Riders can board through the front door and exit from the back door. Here though is where, no pun intended, the rails begin to split.

Chicago: We seem to have more main roads and therefore, more busses. It’s easier to access public transit. The grid structure of Chicago also makes navigating it a zip! Additionally, the EL has many different lines running around the loop and branching out all of the city – it’s good to live off a train line. When it comes to driving, Chicago is NUTS. God help you if there is rain or snow.

San Francisco: Many different types of cars – rail, cable, or busses. On most MUNI busses, you can also board from any door on the bus as long as you have a Clipper card. The public transit network however seems less extensive in San Francisco. You might have to walk a bit [up a hill] to get to the nearest bus stop or bus line you need. The BART also seems like a headache with all the different lines sharing platforms, whereas in Chicago, all the colored trains have [mostly] their own platforms. Driving around San Francisco is a breeze. People aren’t total asshats, the bikers have their own lane on almost every street, and the city is a completely manageable size.

I haven’t had a terrible time riding the MUNI or the BART, but, I think Chicago takes the cake here. Rides seem to be more consistent, more extensive, and more available.

2. City services – Recycling, compost and mental health – oh my!

Citizens of both cities should count themselves lucky! With many services available, including public transit and bike sharing programs, living in a larger city has its perks.

Chicago: Chicago has all the basics – state aid, recycling, assistance for the homeless etc. There are mental and emotional health services available, but they can be hard to find and are in really high demand. Chicago also has a very high poverty population which puts a lot of strain on an already overworked institution.

San Francisco: If you like variety, San Francisco is for you! You can sort your trash three ways – regular trash, recycling and compost!

Green for composting, blue for recycling, and black for regular trash.

The city also seems very focused on it’s citizens. San Francisco is one of the first cities to mandate that companies offer family leave for all new parents – 100% paid for 6 weeks! There is assistance for the less fortunate and mental health services seem to be more available here as well.

For city services, San Francisco is sharing the love a little more.

3. The wind – whoosh!

Chicago is known for being ‘The Windy City’ so you might expect it to be the automatic winner here – but don’t be so quick to judge! San Francisco is blowing back. Ultimately though, both cities are worth of Totoro whisking through them!

Chicago: Consistent wind, no matter what the season is – including winter. The lake provides downtown Chicago with some additional points, but even the suburbs can keep their breeze here. I’ve gone around a corner downtown and been caught in a wind sweep so strong I had to muster the force to push forward.

San Francisco: The Ocean is a major factor in regards to the on-going wind in the city. I can hear the wind whistling up against my windows and I’m always chillier than I expect. With the bay getting blown from all sides, the whole city has a subtle rustle to it, but never overpowering.

San Francisco tried to hold its own here but, unfortunately, Chicago has blown it down!

4. Ocean front beach vs. lake front beach

Oceans and lakes, what’s the difference? Can’t I swim in both equally as well? NOPE!

Chicago, the lake front beach: With limited lake front space, the beaches do tend to be more crowded. However, being a lake has it’s benefits! Being super dirty is not one of them, that is a lose. But, short lake cruises are really fun and it’s an easy way to go out on a boat [with your flippy floppies]. Secondly, with it being a lake and waves being much more manageable, there are often water based shows like fireworks or jet ski races.

San Francisco, the pacific ocean beach: Always too cold for swimming – psych! Pretty much only the hardcore surfers get wet at these beaches. The sand is soft and the sound of the waves is the perfect ambience for a picnic. San Francisco also has an unofficial nude beach.. +5 points.


The ocean beach does go on forever and ever which is pretty cool. There’s just something about the ocean that beats a lake. Since I wasn’t going to swim in either of them anyway, I’ll take the ocean!

5. Fashion – hipster vs hippie

One thing about Chicago is that all the men look kinda like lumberjacks with their beards and plaid for dayssssss. I’m not against either of these things…I would just like for it to go away as a trend. Forever. Like, die. San Francisco seems like it would be hippies abound as far as the eye could see. Lights, camera, action and catwalk – go!

Chicago: The aforementioned days of beards. Chicago is a very hipster city, which is why I thought it was cool to live there before you. See what I mean?! While most Chicagoans enjoy their muted tones, I like to wear bright colors, flamboyant clothes and am rocking the pink dreads. My old roommate tells me there is a very,  very strong goth scene – I believe it! I feel like most Chicagoans just bought their identities off Pinterest.

San Francisco: Fashion here seems to be much more of a statement of personal expression rather than fashion expression if that makes sense. I feel people here dress for themselves over dressing for a magazine photo shoot. The expression is also subtle. While the dress may be wild, it all seems to blend together very nicely with the city. The gypsy, hippie and flowy look is also more popular here, as well as color. San Francisco naturally has the advantage with the weather, and they are working it!

San Francisco rocked this runway!

6. Diversity – talk about melting pot!

This is less of a comparison since both cities are very diverse, but more of a commentary. Coming from po-dunk Ohio, Chicago was shockingly diverse. When I visit Ohio now I’m like “god, there’s so many white people here...”. Even though the culture shock has worn off, I still enjoy, and relish, the diversity offered by larger cities. MMM…relish.

Chicago: Very hispanic oriented. Everything is in both English and Spanish. We have food from all over the world, and hispanic food is very prevalent. Chicago also sports several ethnicity oriented areas including Chinatown and Ukrainian Village. While diverse, Chicago is still very racially segregated, with groups tending to clump together.

San Francisco: Rocking not only a hispanic influence, but also an Asian one! Instructions on public transit are in English, Spanish and Mandarin. Chinatown in San Francisco is much bigger, more expansive, and feels more authentic than its Chicago counterpart.

Not far from Chinatown is Japantown which has it’s own very distinct flair. As a whole, San Francisco seems as equally diverse in culture as Chicago and also in financial disparity.

Ring – TIE!

7. Pizza – who has the better pie?

Pizza is a hot topic with Chicagoans. I’ve seen nothing less than a Malort shot battle (this is not something you want) to settle who gets to pick where the pizza comes from. Let’s see if San Franciscans are as pizza-passionate.

Chicago: Three words: Deep. Dish. Pizza. It’s my favorite, and that it is all to be said.

Chicago deep dish. I dug through 4 years of Facebook photos to find this. We’ll be fixing that when I get back to Chicago.

San Francisco: When looking up the highest recommend pizza place in San Francisco (aka best Yelp reviews), Little Star Pizza took the top of the list with 2,505 reviews and a 4.5 star rating. Luckily, they also serve deep dish, of which, I happen to be an expert.

Measuring in at 9″, this meant I could have more than one slice of this pie. Okay,.. more than two slices. Okay, … – nevermind. Look at these cliche stringy cheese photos:

Being mindful of overall cheese, crust, sauce, and flavor I give San Francisco’s deep dish a 4/5! Not as much cheese as we do in Chicago. The crust was kind of corn-bread-style so I’m glad I got the extra marinara sauce.

This pie blew it out of the park on flavor. Holy herbs and spices, perfectly roasted garlic and fresh mushrooms. THE BEST.

8. Media and advertising – uplifting vs. efficiency

As leading cities in the states, both San Francisco and Chicago are advertising battlefields. On public transit, billboards, on buildings, street handouts – everywhere.

Chicago: Whenever I see an ad in Chicago, it seems to be trying to make me more efficient. More cell data for less money, a way to get your work done faster etc. Always with the rush. That’s not a bad thing! It suits the city – Chicago is always poppin’!

San Francisco: San Francisco has just as many ads as Chicago. The ads here though seem to be more geared towards services and positive things. Learn how your children learn best, public resources, or just straight up kind messages. Also, lots of marijuana ads which is always a plus!

9. Drinking – booze is good.

I have to admit, I expected San Francisco’s stoner culture to be more obvious to me since Marijuana is so accessible. Its obvious in a way – people smoke weed on the sidewalks. You sometimes smell it on public transit when someone is heading home from the dispensary. Overall though, I’d say that drinking is still the oldie-but-goodie for socializing.

Bloody Mary and Mimosa, two winning favorites!

Chicago: Chicago, honey,…you are a drinking city with a sports problem. Seriously, when I moved to Chicago there was so much booze. So many drunk nights. Every bar has great PB&J specials (PB&R + Jameson shot) for $5. How could you resist this? Chicago is also sporting the good ol’ Malort, boozy ice creams, and more breweries than a hipster heaven. Combined with our multiple stadiums and Black Hawk pride (true story: many employers break
from work if your office is along the parade route), it makes for the perfect storm of sports-crazed-drunkenness. Let’s not even talk about St. Patrick’s day.

San Francisco: Talk about a good cocktail or a glass of wine, San Francisco has my number. From Tiki bars to spritzers, this city knows what I like. I admit I haven’t done too much drinking here since I’m kind of a cheap date, but every store sports an impressive wine selection due to the amount of vineyards in California. I’m much more prone to wine and cocktails over beer. Also, because the sports start so early here due to the time difference, those are less hours I have to deal with the crazy brahs!

10. Geography and Terrian

Featuring a large body of water is a perk for both our contestants!

Chicago: Flat. I never truly appreciated this until I came to San Francisco, but that is a huuuuge perk! I would say that Chicago also sports seasons…but it doesn’t. Summer in Chicago is nice, winter in Chicago makes for good alone time.

San Francisco: The hills here are a pro/con situation. They make everything look adorable, but whewww they are hard to walk up. The comfortable and predictable weather here is the big win. If you would love Fall all year round, you’d love San Francisco.

Sticking my toes in the cool grass.

Here we are at the end of our friendly competition!

I could count out some points and declare a winner, but I’m not going to. Sorry [not sorry] if you’re pissed, but I can’t choose between these two special cities! Both of them will always mean so much to me and I love all my city children equally.

How do you think the list measured up?

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xoxo <3


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