Chicago vs. San Francisco

When choosing between Chicago and San Francisco, travelers can find themselves in a conundrum. Who wouldn't, especially when faced with the difficult decision of judging which city is superior? Both are armed with unique charms, from bustling downtowns to iconic landmarks filled with so much character and culture. At the end of the day, the only way you'll get your answer is to consider your personal preference at the end of this read.
Chicago vs. San Francisco

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Hands down, go to Chicago if you favor a sprawling metropolis surrounded by many natural hotspots. It’s also the best place if you have the heart for everything tasty, from deep-dish pizza to one-of-a-kind frankfurters. Plus, don’t forget that the Windy City is known for its awesome skyline, with concrete giants stretching far and wide.

Meanwhile, head over to San Francisco if you’re more of a culture vulture. Here, you can get your fill of the prettiest eye candy and stuff your camera roll with golden landmarks. Don’t forget the rich culinary experience the city offers and taste dishes outside of the local scope!

Still torn on which city reigns supreme in your heart? This article may just help you solve the dilemma you’re in!


You know what Mark Twain said about Chicago – it’s always a novelty! It’s never going to be the same city you saw the last time you dropped by. Instead, brace yourself for its infinite faces, from the many nature parks to its bountiful concrete behemoths. What’s more exciting than that, right?

Chicago is loyal to its nickname, the Windy City, and is as fickle as, you guessed it, the wind! One moment, you’ll be touring its streets and admiring the many skyscrapers well-known throughout the globe. The next, you find yourself enjoying the tranquil lakes and basking in the sun’s warm light. And at night, you’ll be surprised at the sudden shift in the atmosphere and the instant appearance of pubs and music bars.

Eager to know more about the different identities that make up this state in Illinois? Well, get ready to marvel at Chicago and everything that makes it one of a kind.

What Makes Chicago Unique?

The City in a Garden

There’s a high chance you’re no stranger to cities possessing mini-pockets of nature. Maybe you’ve toured several of them and marveled at how they preserved these spaces despite the many urban areas. However, have you heard of the opposite? If not, you’ll be thrilled to witness Chicago in all its natural glory!

This city in northeastern Illinois can not only boast of its phenomenal hotdogs and deep-dish pizzas. It’s also worth noting as a mini suburban area surrounded by miles and miles of natural scenery. In fact, even its motto is a dead giveaway of its vast collection of nature – urbs in horto. It’s a Latin phrase translated as ‘city in a garden’, fitting for a concrete spot enclosed by many greeneries.

First off, Chicago is rich in nature parks. There’s no shortage of these hubs in the city – and the best thing of all? They’re mostly accessible to locals and tourists alike. This means you can sprawl on the grass, marvel at the sky, and pass precious time close to Mother Nature anytime you want!

You can also host a picnic with your family or marvel at plenty of scenic lakefront parts. If you’re more into physical activities, then Chicago also has some hidden gems for you.

Many public parks double as hiking spots for novice and experienced nature lovers. Or, for a more romantic experience, why not avail a bike in one of the rentals nearby? You can even go on a kayak tour or hop on one of the many sightseeing cruises around the city for a unique skyline view!

Additionally, there are also conservatories and botanical gardens throughout Chicago. It’s where you can go to satisfy the botanist in you or if you’re eager to improve your blessing of having green hands. Who knows, you may even find yourself purchasing a seedling to nurture once you get home.

For the Foodies of All Stripes

If you’re on a journey to find the best-tasting cuisine of all time, you can never go wrong with checking out Chicago’s food scene. It’s an elite experience that will make you question everything you’ve heard about the Windy City’s gastronomy. Who knows, this city’s cooking may even be a part of your best-of-the-best foodie lineup!

For starters, there’s the world-famous Chicago deep-dish pizza. It’s a combination of gooey cheese, chunky tomato sauce, and golden crust. It’s a dish so tantalizing that it will send you straight to foodie heaven! You’ll enjoy the savory experience of biting into the tastiest thick crust ever, on top of uncovering layers of fillings.

Next, look forward to another food you can’t miss: Chicago-style hotdogs. It’s a classic dish much more than a standard frankfurter on a bun. Think yellow mustard, white onions, relish, dill pickle spears, tomato slices, and sport peppers – they give this dog its signature kick! Of course, it’s not for the faint of heart (and tastebuds!), but it’ll satisfy your cravings for spicy goodness.

If you’re not into these global favorites, there are still unique treats waiting for you in the Windy City. You can try their take on Italian beef sandwiches, known for being the stuff of legends. In Chicago, you can try this the crispy way, in which a thinly sliced roast beef is served on a long roll with pickled vegetables and hot peppers. You can also order them ‘wet’, wherein you slather your sandwich with plenty of gravy, sweet chili, and hot giardiniera.

Are you in the mood for something sweet? Then go out on the streets and choose from the many stalls of yummy ice cream sandwiches! They come in various flavors, from salted caramel to fresh, fruity strawberries. The sandwich is served between two warm slices of cake or lightly roasted cookie dough. It’s a decadent treat that is perfect for cooling down after going through Chicago’s many sites.

All these food are simply samples of everything you can experience in the Windy City. Consider them the tip of the iceberg in Chicago’s gastronomy, and look forward to the foodie galore waiting for you in the area!

Heed the Call of Music, Cocktails, and the Disco Ball

There’s nothing the combination of phenomenal music and a fun night out can’t cure, especially if you’re jiving out under the disco ball. Pair these up with the most delicious and colorful cocktails you’ll encounter your whole life, and you’re solved! They’re sure to lift you from any slump and awaken the party streak you didn’t know you had all along.

And where best to experience these potent antidotes than the Windy City itself? If you’re not aware, Chicago is considered the gem of all hidden gems in music. It’s home to some of the most talented musicians, offering the most diverse sound scene you’ll ever encounter.

There are their legendary jazz clubs where you can have the time of your life listening to lively boogie-woogies. One great spot would be The Green Mill, the oldest jazz club in America. Or, if you’re looking for something more low-key, there’s also the Jazz Showcase in South Chicago Loop. It’s where you go if you want to witness veterans and experts in the jazz scene, including Andy Brown and Mike Smith!

If blues are more of your cup of tea, there’s also the Buddy Guy’s Legends and Rosa’s Lounge to drop by. Chicago is also known for nurturing its blues culture, so you have plenty of options. Of course, don’t forget the abundance of electronic and live music venues in the city every night. Even if you’re not a fan of any genre in particular, these performances are bound to put a smile on your face – maybe even tap your feet along with the beat.

Looking for something more than these musical wonders to spice up the nights throughout your trip? Then be pumped to know that Chicago’s avenues are also packed with electrifying nightlife hotspots! From waterfront bars and cabaret-style lounges to posh nightclubs – you’ll find something to your taste here in the Windy City.

For instance, you can explore and discover the encounters the Gold Coast has to offer. It’s a chic neighborhood where you can find and experience everything about the clubbing scene, be it a cozy, intimate one or a wild ride of fun.

On the hunt for something more out-of-the-ordinary? Then the Chicago Magic Lounge in Uptown will draw you in at first glance. It’s a speakeasy-style pub dedicated to magic, literally. Brace yourself for close-up magic shows and theater performances mixed with more than a dash of the finest cocktails in town. It’s sure to be a delight for every kind of tourist, even more so for night owls!

Among the Skyscrapers

Hong Kong may take the crown for having the most skyscrapers in the world. However, did you know that these buildings that touch the clouds won’t exist in the first place without Chicago? After all, it’s the city where all the concrete giants originated; you can even dub it the birthplace of these structures which scrape the sky.

Surprised? Well, there’s no blaming you if you’re in disbelief! After all, the Windy City is well-known for its untouched natural hotspots and its saying: urbs in horto. It just doesn’t seem plausible that a city filled with nature preserves would also be where concrete behemoths originated. However, Chicago is a great paradox of technology and nature rolled into one big area.

Initially, it was the city’s attempt at fireproofing its architecture to prevent the repeat of the Great Chicago Fire in 1871. The architects of the era took inspiration from the Eiffel Tower and created metal buildings. These are so tall you’d think they could touch outside the atmosphere. Not only are they intimidating, but you’d also marvel at how skilled the human hands are that made them possible!

One world-famous example of these behemoths is the Willis Tower, which you may know as the Sears Tower. It’s the city’s tallest skyscraper spanning about 1450 ft (442 m), and the second-highest one in North America! Here, you can enjoy the entirety of Chicago’s cityscape through The Skydeck. If you’re lucky and the skies are clear, you can even witness the grandeur of four nearby states!

Another giant to look out for in Chicago is 875 North Michigan Avenue, formerly known as the John Hancock Center. Locals affectionately call it The Big John, so remember to mention this nickname once (or twice!) to fit right in. A tour of this building will provide you with every good thing possible, such as tasting the ultimate dishes from The Signature Room.

There are plenty more concrete giants in the vicinity, so you should keep your eyes open in the Windy City. Who knows, maybe you’ll find your favorite vantage view where you can snap countless photos of one of the prettiest skylines on the planet.

San Francisco

If you want to be in a place that pushes you to have a golden state of mind, look no further than San Francisco. It’s dubbed the Golden City for more reasons than one, so really, is there any other choice? Golden beaches, golden sunsets, and the Golden Gate Bridge – it’s a city that has perfected the formula for an ideal vacation!

You won’t want to leave once you step foot in this sunny state of California, even more so after you experience everything it offers. There are beautiful sceneries everywhere you go, ranging from nature-given gifts to man-made art. Plus, don’t start on its many cultures – it’s like visiting many countries in one spot! Also, don’t miss out on the divine culinary creations you’ll encounter, from local ones to those made with a nice outlander touch.

Still curious what is it about San Francisco that makes it golden? Book a trip, and you’ll find out!

What Makes San Francisco Unique?

Huge Arsenal of Eye Candy

San Francisco is a city not lacking in anything – it will make you feel full with its many splendors. These include satiating your cravings for eye candy, be it man-made landmarks or natural hotspots. Truly, the Golden City is a fitting name for a place so perfect, surrounded by beauty on all sides.

First, the Golden Gate Bridge, San Francisco’s orange beauty, needs no further introduction! It presents you with a majestic view of San Francisco Bay and is considered one of the most famous landmarks in the city (if not the most!).

You’ll have plenty of chances to witness eye-catching bright orange towers and miles of beautiful sunset vistas. Even on a cloudy day, you can enjoy the bridge up close, maybe rent a bike, and cycle across it.

Don’t forget the Painted Ladies located on the edge of Alamo Square. They’re rows and rows of lovely houses that takes you back into a bygone era, particularly the Victorian period. Hint: it’s where they shot some scenes in the hit Korean series Full House, so it’s a must-visit if you’re a fan. These houses are a sight for sore eyes with their intricate woodwork, stained-glass windows, and decorated porches!

These spots are just starters to the eye candy you can find in San Francisco! To give you an idea for your city itinerary, you can also check out the following sights:

  • Palace of Fine Arts
  • Lands End Labyrinth
  • Japantown Peace Pagoda
  • Baker Beach
  • The Presidio

The Streets Are for the Artists

Some cities are obsessed with having their walls spotless and squeaky clean. Others would spend much of their budget on regular renovations to ensure no lasting mark. San Francisco, on the other hand? Well, this city has it all: culture, diversity, architecture… and a whole lot of street art!

That’s right; the Golden City isn’t just shining vibrantly because of its gleaming hills and yellow sunsets. It’s also golden in terms of its stunning array of murals and graffiti. It’s the perfect place for artists who want to express themselves without the restriction of easels and mini-paintbrushes. It’s also the ideal place if you have the heart for bright, colorful creations and creative masterpieces.

Walking down the avenues of San Francisco will take your breath away, literally. It’s like walking in a different world, where everyone can converse in a language beyond the human tongue. From back alleys that tell various political tales to works of the most intriguing lines, this city is a full-on evolving masterpiece!

Curious about which of San Francisco’s street arts will appeal to you? Maybe you’re more adventurous and eager to explore every inch of the city to uncover its many artistic treasure troves. No matter which it is, don’t forget to check the Golden City’s many alleyways!
More often than not, you’ll find the most beautiful graffiti pieces created by locals. You can also look forward to plenty of thought-provoking murals that will stick with you long after your trip to San Francisco is over.

Birds of Different Feathers Also Flock Together

There’s just something about San Francisco that attracts many kinds of residents. Is it its golden reputation, especially with its ever-growing tech industry? It may be its many wonderful landmarks paired with the perfect sunny weather that knows no cold. Or it’s due to the city’s wonderful gastronomy, composed of steamed beers and clam chowder bread bowls said to enchant any man?

No matter what it is, there’s one thing you can’t deny about the Golden City: it’s a phenomenal melting pot of culture! You’d find an infinite array of people in the area, each building colorful lives, and dreams. In this city, you learn from different cultures and pick various beliefs – maybe you’d even choose to settle in the area yourself.

First, San Francisco has an authentic Chinatown, unlike other imitations you’ll find in other tourist spots. It’s the biggest out of the four Chinese districts in the city, with plenty of Chinese immigrants present until today. These Asian settlers arrived in the Golden City in 1848 and grew into a thriving business community. The result?

A bustling, bright section in San Francisco where you can find wonders of all kinds! Here, you can taste only the most authentic Chinese cuisine, such as jian dui, char siu, and man Sichuan-style dishes. After eating your fill, you can also marvel at the Chinatown Dragon Gate and the Tien Hau Temple.

Aside from getting a tour of the best Chinese culture, the city can also provide you with a vibrant Latino neighborhood. It’s known as The Mission, a must-visit enclave for those who love tacos and burritos! More than that, though, this San Francisco cultural spot is also home to many bodegas, posh retail shops, and thrift stores.

You can access the heavenly Nieves Cinco de Mayo, a hub of delicious Mexican treats in this Latino neighborhood. Get a taste of the Bionicos or the Raspados, sweets that caught the hearts of many travelers. If you’re feeling bolder, try the Mangonada. It has endless mango layers sweeter than the last, mixed with lime and tamarind for a kick!

Home of Riddles Wrapped in Crispy Goodness

Are you a huge believer in luck and endless possibilities? Maybe you find inspiration in Virgil’s well-known saying, ‘audentis fortuna iuvat’? Well, no matter what it is, you’d definitely find a calling in San Francisco, the birthplace of fortune cookies!

To be specific, many people believe that Makoto Hagiwara invented the original recipe at the Japanese Tea Garden in Golden Gate Park. Others claimed that the cookies were an original creation by an employee from San Francisco’s Kay Heong Noodle Factory.

These legends have been passed down through generations of San Franciscans, making them an important part of history. You can even find variations of these sweet cookie wafers throughout the Golden City, be it a small-scale restaurant or a huge specialty shop.

Not familiar with the joy the fortune cookies bring?

Well, it’s high time you step up and try them out in their city of origin. They’re sweet treats filled with small slips of paper containing varying messages. Some have texts you can’t help but laugh out loud; others contain inspirational ones that can take you out of any gloom. Other cookies even have predictions, and they often have a special meaning for that particular person.

Think this is only San Francisco is good for? Well, you thought wrong. Fortune cookies only serve as an appetizer or a dessert for some of the best-tasting dishes you’ll ever know. Brace your tastebuds for the many culinary masterpieces the city offers.

First off, you can pair your lucky cookies with the Golden City’s very own take on Irish coffee! That’s right; you would think finding an excellent cup of this variation in San Francisco would be like finding a needle in a haystack. However, you’re lucky since this city is well-known for crafting some of the best Irish coffee!

And if you get hungry, why not try San Francisco’s many delightful meals? One of these is the Cioppino, a simple dish made by Italian anglers in the Golden City. It’s a broth based on tomatoes, with plenty of seafood to sweep you off your feet. You should try this out if you’re a fan of crabs, calamari, and mussels. There’s also a bit of wine included in the recipe, something you can always look forward to.

You’d feel your fortune growing every minute you explore the meals in the Golden City. Maybe it already did the moment you chose it as your destination or after you cracked open your first local-made cookie of prediction. No matter what, you’ll never tire of San Francisco’s food scene, so be bold and have a taste test galore!

Is Chicago or San Francisco Better?

When it comes to comparing Chicago and San Francisco, the debate is ongoing. While both cities have their unique charm, many people find themselves trying to decide which one they like best. Ultimately, though, it’s all about choosing the one that speaks to you best.

If you’re looking for a destination with a more casual, laid-back urban vibe, then you can’t go wrong with Chicago. It’s a paradox of a city known for combining concrete behemoths and thick natural hotspots. It also possesses some of the greatest music and nightlife of all time, so you can let your hair down with wine and a lot of dancing.

On the other hand, San Francisco has a vibrant city scene full of culture and exhilaration. Here, you can enjoy the perfect weather and the sceneries that make this urban area worthy of the title ‘The Golden City’. On top of that, this place is also known for being a cultural melting pot. Get ready to expand your palate and knowledge of different humans and their traditions!


Chicago vs. San Francisco Weather

The weather conditions in Chicago and San Francisco vary greatly; you could even say they’re on two different spectrums. The former is known for its windy weather and cold winters, with sky-high temperatures over the summer, too. Meanwhile, the latter has pleasant weather all year round, shown in its abundance of warm, sunny days.

To give you more details, summer in the Windy City can get over 83.9°F (28.8°C). The winter months can get as low as 19.2°F (-7.1°C), while the rainy season can yield over 38 in (970 mm) of rain on an annual average.

On the other hand, summer in Golden Gate City only gets up to 67.2°F (19.6°C). Winter weather can reach only about 45.5°F (7.5°C), with no chances of snow at any time of the year. Chances of rain are also low, with about 24.6 in (624.84 mm) on average per year.

Is San Francisco in Chicago?

No, San Francisco is not in Chicago. Instead, it’s a city in the state of California, located in the western part of the USA. Meanwhile, Chicago is in Illinois, in the midwestern region of the United States.

Chicago to San Francisco Distance

The distance from Chicago to San Francisco depends on the mode of transportation used. If you’re traveling via plane, you only have to cross about 2985 km (1855 mi). You’ll also travel the same length if you take the indirect railway route going from Chicago to Emeryville, then commute to the Golden City.

On the other hand, going from Chicago to San Francisco via car will depend on the route you take. However, the average path spans approximately 3432 km (2133 mi).

Chicago to San Francisco Flight Distance

The flight distance from Chicago to San Francisco is 2985 km (1855 mi). If you’re traveling at an average speed of 805 km/h (500mph), you’ll reach your destination after 3 hours and 42 minutes. Note that you may arrive earlier or later than the average time due to the type of aircraft used, its route, and the weather conditions.

Chicago to San Francisco by Train

If you’re planning to take a train going from Chicago to San Francisco, there are two things you must know. First, Amtrak is the only train line you can depend on when traveling this route. Second, the company has no train station in San Francisco, so there’s no direct railway between the two cities.

Amtrak trains going from Chicago to San Francisco pass through the Rocky Mountains and the Sierra Nevada. They do so via the California Zephyr course, which would require you to get off at Emeryville, situated beside San Francisco Bay. You can then avail of an Uber, Lyft, or book a taxi to reach your chosen spot in San Francisco.

Travel time spans an average of 52 hours from Chicago to Emeryville via train. You’ll have to cross 2972 km (1847 mi) to arrive at the station. You can then reach San Francisco from there after an average of 13 km (8 mi), with 15 minutes of commuting. Overall, the distance between the two cities is about 2985 km (1855 mi), which will take you over two days to travel.

Sleeper Train From Chicago to San Francisco

There is no direct sleeper train going from Chicago to San Francisco. It’s a pity, especially since it’s one of the best ways to maximize your time when crossing two cities. However, there’s still some good news for you.

Although there is no direct overnight train on the Chicago to San Francisco route, you can access the next best option. This would be availing a slot on Amtrak’s sleeper cars – it’s the only train line that can bring you closer to your target destination. To elaborate, the company’s trains travel from Chicago to Emeryville, a city in California sitting close to the Golden Gate City.

When you avail of a ticket for Amtrak’s sleeper cars, you’re privy to many amenities, including restrooms and showers. You are also provided with free meals and a cup of coffee.

Luxury Train From Chicago to San Francisco

The only train line that can take you from Chicago to San Francisco, albeit indirectly, is Amtrak. This company offers no first-class seating, so don’t expect luxury travel when choosing the railway. The California Zephyr route, which you’ll use when crossing from the Windy City to the Golden City, only has coach seats and sleeper cars.

Don’t be bummed out from the get-go, though. Despite having no first-class section, you can still have private rooms and bedrooms if you’re availing the overnight cars. Specifically, Amtrak’s sleeper carriages have two levels, each containing restrooms, and showers. Plus, they have one family-sized bedroom and a single accessible bedroom.

Reserving a slot in their single, accessible bedroom means you have a private shower and restroom. However, if you’re getting their family-sized one, you’d have to share these bathroom amenities with others. Note that these accommodations range from $700 to over $2000.

Scenic Train From San Francisco to Chicago

The Amtrak trains going from San Francisco to Chicago offer plenty of sceneries that can make your jaw drop in amazement. These trains travel via the California Zephyr, which passes from Emeryville, California, to Chicago. There’s no railway in San Francisco, so you must book a short trip to Amtrak’s train station in Emeryville before starting your scenic journey.

The California Zephyr route passes through five wonderful states. These include Nevada, Utah, Colorado, Nebraska, and Iowa before arriving in Chicago. These American spots are known for their unique sceneries, so ensure you get the seat with the biggest window if possible.

Tip: family bedrooms in these Amtrak trains have windows on both sides, so you can witness the wonderful views en route from left and right.

Chicago to San Francisco Drive

If you’re planning to get from San Francisco to Chicago via car, you’d have to drive for approximately 3432 km (2133 mi). This will take you about 30 hours and 38 minutes of travel time if your speed is 112 km/h (70 mph). Note that this is only a rough estimate as you also have to factor in the route you’ll take and the traffic you’ll encounter.

Chicago to San Francisco Drive via Route 66

There’s one thing you should be aware of when driving from Chicago to San Francisco via Route 66: it ends in Santa Monica Pier in California. This means that you won’t be reaching the Golden City directly from downtown Chicago when using this path. Instead, you have to travel about 615 km (382 mi) more, which will take 5 hours and 41 minutes.

If you’re up for it, the drive from Chicago to Santa Monica spans about 3940 km (2448 mi). Crossing this distance will take about 40 hours on average, not including the break and stopovers you’ll be taking. Add the driving time from Santa Monica to San Francisco, and you’ll be behind the wheel for over 45 hours.

Best Route From Chicago to San Francisco

No doubt, the best path to take when traveling from Chicago to San Francisco will be Route 66. The journey is lengthy and tiring, but it’s worth considering all the beautiful places you’ll pass by. You see, it’s not called the Mother Road for nothing, so it’s your ideal choice if you’re craving the perfect road trip.

Route 66 crosses eight different states. These are Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. This means you can travel and enjoy most parts of this southwestern journey without lacking anything. You can witness different sceneries, taste various cuisines, and meet all kinds of people on the road.

The best thing is this: you’re free to stay in any town in all these states for as long as you want since you’re using a car. You don’t have to catch a flight or line up in a queue to get a train ticket.

Driving From Chicago to San Francisco in Winter

Driving from Chicago to San Francisco during winter is a great idea, but only if you’re prepared for it. For starters, you may encounter blocked roads due to heavy snowfall. This means backtracking or stopping at a nearby town until the weather calms down. You should also factor in other dangers, especially if you’re a solo driver steering the wheel through slippery routes.

If you’ve set your mind on crossing from Chicago to San Francisco, then the first thing you should do is secure a map, just in case of a bad signal. Remember to familiarize yourself with different routes in case you have to switch roads. Also, stock up on supplies, particularly food, water, and items that keep you warm.

Remember that your journey between these two American cities during winter may take longer than normal. For reference, the average travel duration from Chicago to San Francisco will take only about 30 hours. However, you have to be mindful of your speed and maybe switch routes multiple times depending on the weather. It’s all worth it, especially if you think about the views and how nice it is to enjoy the trip without too many tourists.

San Francisco to Chicago Road Trip

The road trip from San Francisco to Chicago may be lengthy, but it’s well worth it if you’re traveling for the experience. There are plenty of great stops along the way, so it’s best to take your sweet time savoring them.

One excellent rest stop en route is Napa, a city in California well-known for its wine. It’s a great prelude to your long journey, especially if you love sweet, fermented alcohol. On top of that, the food is excellent, too, be it lamb chops, pizzas, or unique Mexican dishes.

There’s also the city of Omaha, a must-visit for road-trippers with a heart for animals. Here, you can enjoy observing them in the Henry Doorly Zoo and Aquarium. This spot is also known for its long history, large arrays of artifacts, and mystical flea markets.

You can encounter many more cities and towns on your San Francisco to Chicago road trip. Some of them include Sacramento, Reno, Salt Lake City, Boulder, and Madison.